How to Scale SaaS Sales

How do you scale SaaS sales? Set territories, pricing, metrics, and quotas? Build a team? Be a leader? Today’s episode features a panel discussion on Software as a Service (SaaS) sales and scaling hosted by Jono Landon, founder and CEO of Hubbli.

Panelists include Cheryl Fearon, Zensurance sales director; Bram Belzberg, KEV Group CEO; Jordan Grant, Zafin head of business development; and Nick Kozmin, founder. 

Topics Include:

  • What is SaaS sales? Mastering a craft, learning every day, figuring out what works, and how to make it better and easier for customers and team members
  • KEV Group’s growth lifecycle due to product, pricing, and positioning innovation
  • started to help SaaS startups scale successfully through product-market fit, lead generation, selling, and closing 
  • Sales Strategies and Metrics: Selling hasn’t changed, but marketing technology and tools make an impact 
  • Sales Sprints: Implement weekly, monthly, and yearly goals and action items to achieve
  • Successful Strategies to Scale: Hiring practices and personality tests to find top talent that fit with a company’s culture and onboarding process
  • Ideal Customer Profile: Required characteristics of potential prospects include asset size, interviews, and value of solution
  • Conducive and Compelling Candidates: Competencies, hard work, and diligence may not be enough or make someone worthy of position
  • Art of Sales: Customize, interpret, develop, and deliver message to get customers  
  • Content Marketing: What should you do to solve your problem? How can you solve the problem by purchasing a solution? 
  • Salary, Commissions, Compensation, and Bonuses: Different business models that generate motivation and participation  

Links and Resources:


Jono Landon on LinkedIn

Cheryl Fearon on LinkedIn


Bram Belzberg on LinkedIn

KEV Group

Jordan Grant on LinkedIn


Nick Kozmin on LinkedIn 

Toronto Software as a Service (SaaS) Meetup Group

Predictable Revenue by Aaron Ross


Caliper Test


Salesforce Methodology








Google Analytics


Ring Central




“Sales is like mastering a craft. It’s about learning every single day on what works, what doesn’t work, and how do you make it better and easier for your customer and your team.” Cheryl Fearon

“Selling hasn’t changed, but marketing has changed to make an impact.” Nick Kozmin

“Solve one problem for one person.” Jordan Grant

“Any good sales leader is going to be…agile. They will try and test a million different things.” Bram Belzberg

Episode Transcript

Jono: Hello and welcome to the Kick SaaS Podcast. I’m your host, Jono Landon. In this podcast, we share excerpts from live in-person SaaS growth events that I run here in my hometown of Toronto, Canada. A little about me, I’m the founder and CEO of Hubbli, a B2B SaaS company that helps private schools find new families to enroll and engage them throughout the entire enrollment journey. This episode is a recording from a recent panel discussion that I hosted and moderated at the Hubbli head office here in Toronto on the topic of SaaS sales and scaling.

The panel included four members of Toronto’s top SaaS sales leaders. First we had Cheryl Fearon, who’s a Sales Director at Zensurance. Also, we had Bram Belzberg, CEO of KEV Group, also a recent recipient of Canada’s Top 40 Under 40 award. Jordan Grant is the Head of Business Development at Zafin. We also had Nick Kozmin, the founder of This panel discussion offers many takeaways for anyone who is involved in scaling a SaaS sales organization.

We’re going to jump right into this episode and I hope you enjoy the format and content we go through here. I look forward to sharing future episodes with you from these live SaaS growth workshops.

Thank you. Thanks, Margie. My name’s Jono and I’ve been working in the Internet world since the early 2000s. I started out in a sales role, moved into sales management, then marketing management, and then I got into product management and did that for about five years. I launched Hubbli about five years ago where I’ve been doing everything. Thankfully, in the last year-and-a-half, I’ve been able to really focus again almost exclusively on sales and growth. I’ve been really excited to be connected with people that are focused on sales growth.

What we do is we see it as ranging the spectrum from marketing and lead generation, all the way through customer success, all the different drivers of growth. That’s why we started this group and it’s exciting to have such an amazing panel here tonight. I want to personally thank everybody for coming. It’s a real honor to have you all here. Also, I want to thank everybody for joining us, especially on a cold rainy day like today, so thank you. I’ll pass it on to Cheryl. I’ll let her introduce herself.

Cheryl: Hi, everyone. My name is Cheryl. I’ve been in sales my whole career. In sales, started with inside sales, outside sales, I’ve moved up through leadership positions. To me, sales is like mastering your craft. It’s about learning every single day on what works, what doesn’t work, and how do you make it better and easier for your customer and for your team. For me, it’s been a lot of years of evolving and really trying to figure out, “How do I this better and how do I do it better for my customers?”

I’m with Zensurance today. I’ve worked for a number of startup software companies and technology companies from big and small. Really, what I love to do is to take the company from here and build it up to here. When I started at Zen, I had three sales people in my team. Today, my team is 30. It takes a lot to be able to build a team, make it cohesive, bring everyone together, figure out a magic solution, and help that to scale. I’m hoping I can share some of those thoughts with you today.

Bram: All right. I’m Bram Belzberg. I’m the CEO of KEV Group. For those of you who don’t know KEV Group, it’s a provider of accounting and online payment software almost exclusively to public schools across the United States and Canada. More specifically, we have an accounting product and then the ability for parents to pay for all their kid’s school fees. We operate in just over 18,000 schools across North America now. I’ve been in the business for 10 years.

It was founded by two amazing ladies, Kim and Ev, who are still with the business, actually. They founded the business and they worked at the school district. They left the school district trying to solve a problem that they had identified at their own home base. They created a solution and realized about the heads and legs, eventually left the job, and created a little company out of it. Maybe 12 or 13 years later, I got introduced to them after business school. I joined up as the COO and then the CEO six months later. I’d been there for now 10 years and we’ve been growing at a pretty fast pace since.

One thing that’s interesting about KEV for this particular discussion is where we are in our growth life cycle. We’ve done a lot of product innovation, we’ve done a lot of pricing innovation, a lot of positioning innovation over the years. We were first in our market, selling online payments in Canada so we had to come up with the whole pricing model that would work. We did that through trial and error many, many times over and we went through that. Even today, we’re innovating on our modeling and our pricing again.

The other thing that’s interesting is that a year ago plus two days, I know we closed our first ever major outside investment from a growth equity firm out of California called Zen Capital. We then made an acquisition, a month later, of  our largest competitor in North Carolina. Along with that, we decided to go from what was basically a two or three person sales team where every individual just sold and there’s no sales leadership or management of any kind. It’s just one of them was the founder […] who is still selling and two other relatively junior people to building a proper sales organization.

We hired Cheryl Fearon, who’s a head of sales and marketing, who’s pretty amazing. We have since, in the last year, gone from where we are now to 15 full-time sales staff including account execs, BDR, and marketing across the board. We’re just assembling our team. I’ve recently gone through, again, how do you set territories, how do you set pricing, how do you set metrics, how do you set quotas, and all that. I’ve been schooled quite a bit recently in that, so I’ve been into that.

Jordan: Welcome, everyone. My name’s Jordan Grant. Today, I’ve been two weeks on the job, Head of Business Development at Zafin. We’re a Toronto growth company. We’ve been around for about 15 years. Recently sold part of our business, about 500 folks to Accenture. That was a multimillion dollar deal that happened in January. We’re about 230 folks today and regrowing the team, if you will, the part of the business that we kept.

Prior to that, in my previous life, I worked at two startups. The most recent one was Flybits as Sales Director, selling into all the world’s largest banks across America. Prior to that, I started my own beacon company. If you know beacons, they never really took off but we made a couple of bucks out of it and did some really cool projects. We built a team up to about 15 people.

I think that was probably the most groundbreaking part of my career, helping a lot of new to Canada. People actually establish their life here in Canada. Some of them have moved back to Mexico or Netherlands and other places. That was the best part of my career even though it was not the funnest of times and most profit-making.

I was brought into Zafin to rebuild the business development team. We have about 35 global clients today. They range from ING, Standard Chartered, Bank of America, the world’s largest banks, but we don’t really have a lot of potential companies or prospects in the pipeline. So, building up the team there, I’m hiring if anyone’s looking. I’m excited to have this discussion. I personally have a spectrum from enterprise all the way through small, medium, and a growth-sized startup. So, I’m really excited to chat.

Nick: My name is Nick Kozmin. I founded We basically help startups scale. I’ve been doing this for about eight years. Two years ago, I came up with a new consulting offer and put my process down on paper. Since two years ago, we sold it to almost 700 companies. Justin’s on my team, actually. We have a few customers here, actually. Bootstrapped it to $5 million in less than a year-and-a-half and we’re operating at $5 million with only 6 people. We’re really lean, mean, and customers are doing really well, which is really cool. I know how to start offers from scratch and get them going without fundraising.

Some of our customers fundraise but we can do a bootstrap and it’s a totally different game. We carved out a niche there and we’re helping entrepreneurs in that way. Most of our customers are SaaS companies, some high tech-service. We focus on product market fit in the beginning, lead generation, and then selling and closing. So far so good, so if you guys have any questions regarding how to make millions of dollars when you’re really young, then ask away.

Jono: Yeah. Definitely good question for the Q and A. I’m going to kick off the panel here and I think what we’ll do is we’ll just let you guys jump in wherever you think you’ve got something to add. Don’t feel pressured to answer, but at least one person has to answer every question, okay? The first question is, how have you seen successful sales strategies change over, let’s say, the last 5-10 years and what were the impacts of those changes on your sales metrics? Who wants to go first?

Nick: I can answer. Sales hasn’t really changed. It’s selling probably to somebody and providing a product. What has changed is the marketing strategies. Ten years ago, email marketing was really big, like cold prospecting. Cold calling was big. Cold Calling 2.0 with Aaron Ross—I don’t know if you guys know him—wrote the book Predictable Revenue and Impossible to Inevitable. He’s actually customer of ours because he wants to do the digital marketing stuff. Now, instead of doing the cold prospecting and cold calling, a lot of the lead generation comes from paid advertising using social platforms and content. I’ve seen that change, but sales is the same thing. If you’re selling over the phone or door-to-door—I started door-to-door—same stuff, at least in my opinion.

Cheryl: On my side I find I agree. The sales haven’t changed but I find our tools are different. Today, there’s a lot of automation tools you can use to make your team more efficient. How do I have an email automation tool that does some of those follow-ups themselves were you can handle more volume, get better sales, increase your sales but take some of the mundane work out of the team? How do I put technology to play to be able to make that easier for my team and to increase the amount of follow up and how do we manage that.

Sometimes that is looking at operational efficiency internally and the sales team loves it because it takes out all of that mundane work where you’re focusing on having good conversations at the right time.

Jordan: Going off of that, I have this motto that delves into the details. So, in my last two roles, I’ve implemented Trello, which is a very interesting tool, especially when it comes to business development because it’s typically known as a product solution. Trello, I break everything down into 10 days sprints. We do a stand-up at the start, a midpoint review, and then endpoint review. The goal here is to have everyone call each other out on what can be done in a two-week period or a 10-day period. It doesn’t have to start on a Monday. It also gives you visibility across the organization to understand what everyone’s working on. It’s really about what can you do in that 10 days? That’s all I care about.

Bram: You’re talking of 10-day sprints for sales teams. That’s cool. We do a week, like weekly goals, and monthly. That’s cool.

Jono: I find that very interesting because when I went from sales management to project product management, I learned all about sprints, becoming agile and everything and I’ve never thought about a sprint in sales. My experience was in the early to mid-2000s was everybody in a room like a bullpen, having everyone’s numbers on the board, and having all that daily sort of rah-rah stuff. I’d love to hear a little bit more about how that’s implemented through a Trello Board and obviously we can’t get too visual here but can you talk a little bit more about that. I’d love to understand practically or pragmatically how does that get implemented.

Jordan: There’s two things. We just implemented it at Zafin. It was, I think, day two that we kicked it off. So, our team of four BDRs, including myself—I consider myself a BDR—list out a lot of the action items that we have to get done in those two weeks that are outside of customer facing, if it’s training or anything like that, and then there is now the clients.

The clients are things like are you reviewing their annual reviews? Are you sending particular information to the client ahead of time? Are you doing customer interviews to learn how better to position your product? You’re mapping out all of the process for a client. We call them cards on Trello if you use Trello, but you take out all the stops in the sales process that you don’t think you’ll get done in that two-week process. As for me, as a leader of the team, I can now evaluate if there’s too much in someone’s plate and I’ll call them out if they can’t get it done. And if there’s not enough on their plate, I’ll also call them out.

Jono: Okay, and everybody can see that, obviously. It’s public within the team.

Jordan: Across the team. Sometimes, the owner of the card, these are individual little goals with task lists inside, so you could comment your boss. My boss actually has a visibility into this. They could comment as to, “Hey maybe prioritize this individual task over the other because maybe we’re looking at investment or something like that.” I wish I could show my Trello board. It’s pretty cool.

I use it for individual life as well that is hidden from everyone. Business development is unheard of. I used to do it in sales and it makes sense, but business development you think all you’re doing is calling people and getting people on the phone, but there’s a lot. If you actually map it out as to all the little minute tasks that you have to get done and all the follow ups and orchestration that you have to do internally, there’s quite a bit.

Jono: Would you be willing to share that with everybody? Can I put you on the spot? Afterwards, can you send out a screenshot or something?

Jordan: We can do that.

Jono: That would be great. That would be amazing.

Bram: How big is a ticket price on what you’re selling?

Jordan: Ticket price ranges from. $200,000. We have one in the Hopper for well over $20 million, actually closer to $30 million.

Jono: Moving on to the next question, if you guys could pick maybe the one or two strategies that you’ve implemented that you’ve seen to be the biggest wins for you in your roles, whether its current role or something in the past. I’d love to hear what those are for everybody.

Cheryl: For me on scaling and growth, I think hiring practices have been huge because I’m scaling so much and trying to centralize what does that look like. My team is too small, but I hire the best. So, how do we really make sure the candidates that are coming in are the best fit culturally to have the right culture for the organization to feed into our growth and to make sure that we’re bringing on the top talent. I’d say that’s been a huge focus for us. I think the second is utilizing tools and technology to create a really streamlined work list. We’ve basically integrated a fair number of tools together to create a seamless work list to help the team prioritize what’s next.

Different from Jordan, we’ve got a lot of volume so how do we manage such a high volume of number of customers and tasks to be able to support what’s important? How do I bring up and flag what order they need to do things to be able to support what’s next? If you have so many things to do, it’s easy to get overwhelmed. So, how do I break that down? Highlight and prioritize that in a simple way and being able to create a work list that organizes it in the right way for the team has been a huge success and help us manage that volume a lot better.

Bram: I’m just trying to look up the name of the software product we put out. We’ve done two things, recently, both on the human capital side. Just to be clear, I think any good sales leader is going to be—I don’t like to use the word—I think that on this panel you’d say agile. They will try and test a million different things and see what works for them. Not just for their company or their product but for that time of the month and that part of the sales cycle. Good sales management in general is always aiding and assisting the salespeople on how to close the deals. That being said, getting good people and making sure that they’re the right fit for the team culturally and that they’re on board at the right way has made a huge difference. We’ve done two things in that regard.

The first thing we’ve done I was just trying to find the name. I will find it and I’ll tell you, but we instituted company-wide personality tests. There’s one in particular and I love it and now I am just completely drawing a blank. I will find it. When the private equity firm invested in us, they asked me to do it and my team to see what they thought of us. What they were able to tell about us just from reading our results was pretty scary.

They were also able to do a bunch of team dynamics stuff which I thought was really, really helpful. I’m super skeptical about this stuff, but I am really drinking the Kool Aid on this right now. So, we’re now thinking how can we push this deeper into the sales process. When you hire a salesperson, you spend a lot of money on them. You train them, you onboard them, and then you give them a 6-9 month ramp before you can judge them, then you’re talking about a $250,000 investment into one person, not to mention the opportunity cost which is many times that.

If you can decrease the chances of you being wrong by 10%-15% percent, that’s a multi-hundred thousand dollar per person yield. It costs $100 to do the test and it takes an hour. I considered almost a no brainer. We’re really seeing how we can push that out without making people feel uncomfortable while using it the right way and there’s a bunch of pieces of that. That’s brand new to me.

The other one that we did was, as I said, the two founders of the business are both still with the business. Kim is still a sales person and doing amazing. We have asked her to sell less and train more and people are able to model their behavior off of her because she’s been doing it for 25 years, selling this specific product. Whereas the new people that we’re hiring are very process-driven—she wasn’t as process-driven—she’s unbelievably capable on the specifics.

The other thing we did, that was Evelyn, the other founder—Kim and Ev makes KEV—I tasked her with starting an onboarding program company-wide, which we never did. Now, every new person that comes in does a week intensive in-class—it’s a board room and there’s 5-6 people around the table—where we bring in product, values, culture, history of the company, how to use the phone system, all that stuff.

Then, every month there’s more classes, there’s more dinners, there’s more buddying. We’re […] to it. This just started a few months ago. I’ll tell you, the impact has been mind-boggling for what it’s done. First of all, when people leave that week they are so fired up and may feel like so much part of a team as opposed to before, especially because salespeople, at least in our business, tend to be remote.

You hire someone in Timbuktu, they might never meet anyone on the whole team other than on the phone. To bring them in and give them a week of FaceTime, get them to go out for drinks at night and all that has been so much more important than I gave it credit for. Also, the time to successes shrunk and the unwanted turnover had shrunk. It’s just been really, really positive. We’ve been constantly testing and adapting our model to figure how to scale and things like that on the human capital side I had, by far, in the way the most yield.

Jordan: One of the things that I learn from a couple of failures was really finding out who your true customers and what I call an ideal customer profile. Really identifying technographics from a graphics operating model, all the things that fits within your model or within your ideal customer, and never deviating away from that.

Bram: Sorry, what is that? What are technographics and […]?

Jordan: It’s like information for banks would be like asset size. Asset size below $25 billion, we’re not chasing. If someone literally comes to us at $23 billion, then we’re not going down that road with them.

Bram: So, you want to know better information about your customers?

Jordan: Characteristics of our customer, they have to meet the characteristics for us to explore that customer. The idea you can also have depending on the size of your company and where you’re at, you can also include an acceptable profile, which means if we sell the banks—we’re maybe an auto financing company which is pretty well a bank; they do auto financing very well—we might be fit within that acceptable profile.

The idea is that you hold true to who your customer is and you never deviate. It reduces a lot of wasted time. Your product being pulled in all different ways and then you never get to build the product that you originally set out for because someone else asks for something else. Sure, there’s deviations that are good for the company, but in most cases I find has crippled companies.

The other big one is doing customer interviews. Some proponents of being able to actually identify what do they feel as though my company provides to them. What’s their unique selling propositions? What’s their operating model? Where do they measure it on? Really identifying those things initially will help you. What they tell you is better than any marketer or any sales person within your organization.

I actually mirror it to someone in your product team. Someone in your product team will actually boil down what you do and the value of your solution because they’re the ones that built it, they’re the ones closer to it. Everyone else muffles the messaging you truly don’t really understand and I find you always go down that path that’s not really a strong one.

Nick: Yes. Those are good points. What size is your company? Just starting? Under a million? Over a million? Over 5 million? I agree. We’re at that stage now. I think you’re mentioning it like the culture and that hiring. That’s probably the number one thing for us now is finding the right fit. They’re in social events and getting everyone involved. So, I agree with that a lot. We didn’t find that important until we hit a certain stage. In my opinion, it depends on the size. In the very beginning, it depends if you’re like $100 million. Focus on the target and the problem that you’re solving. That’s the main thing. Once we found out who we are going after, we dialed in the problem that we’re solving and we saw the […] out of it.

That’s when we shot up to $1 million in a few months and then to go from 1–5, it was more dialing lead generation, getting that consistent, and then dialing the sales process. Now after five, it’s like getting the right hires, making sure the culture’s right. That’s going to take us to 10 and passing off some of that responsibility.

I definitely agree with your points. We’re finding that to be a problem now. We’re putting more emphasis on bringing more people in, but in the very beginning it’s really solving a problem, making sure it’s a really painful thing, and I know some of our customers, we dialed in your offer, right? As soon as we tightened it up, you started seeing growth, right?

Jono: Yes. I was actually going to mention that. That was for us a really incredible transformation. We were just solving too many problems for too many people, so it made the sale way more complex than it had to be and it actually made every metric not as good as it could be. I was just at a point where I was like, “Okay, well, either I need to stop selling and go raise a bunch of money or I have to figure out some things.” I came up with a scrappy idea which was accumulating after a year of getting a lot of requests for one thing in particular When we really looked at it, it ended up being the biggest problem for our market. It was one of the things that our platform did and was doing for customers. We said, “Okay, let’s really dig into that” and we really scoped down what our solution was doing. This is really a repositioning of who we are and who we are for in the organization.

I really credit Nick because he really gave me that kick in the pants to solve one problem for one person. Once we did that, all of a sudden we could close deals instead of an average of three calls, we could do it in one call. Because we really narrowed down the scope of what we are offering, we could go a little bit deeper in value and more than double our prices. Every sales metric just shot through the roof and it was easier to onboard them. Our onboarding time went down by 90%. I did a whole talk on this about niching in different ways in our last meet up, so I would say that was something.

To Bram’s point, in previous organizations, I was always into this personality assessment thing. I’ve done like everyone that exists on myself. I think they’re just so fun to do. I don’t know why, but I have a degree in psychology, I guess that’s why. They’re so consistent and it’s really scary how easy it is for a test to tell you about yourself, but they’re right. I’m actually interested to hear how you implement that information because obviously you can’t. I don’t know if you can legally not hire somebody for their personality. I don’t know, maybe you can, maybe can’t. I don’t know, but all I know is hiring people is really scary when it comes down to law and I can never just ask people what I want to know. I always have to like dance around it but I would love to hear about how that’s implemented more in a sales environment.

Nick: We have not rolled it out on sales yet. We use it on senior management and then, literally very recently, we’ve decided to push this down. We already put on everyone a director and above and I recommend that we move it down one or two more levels and that’s what we’re testing. First of all, I looked it up. It’s the Caliper test is the one in particular that we use. It’s called Caliper and the private equity firm, Sarens, use it on everyone on their portfolio companies and its standard operating procedure.

Bram: Do you know they look for? Do they share that information with you?

Nick: Yes. One of the things that they have and I don’t know if this is done by Caliper or if it’s done by the users, but they’ve developed profiles. Let’s say I’m a CEO so they want a very self-directed person, someone who’s not going to be overly concerned with whether everyone around the table has a say in everything but someone who is going to be able to develop a strategy and stick to it and explain that clearly to the organization.

The things that make a good CEO do not necessarily […] a wonderful head of HR or a wonderful head of product or a wonderful head of development. It’s just different. I don’t have the keys, if you want to call that. That’s something we’re looking into now is do we develop our own or are there standards? Can we go and take training from the organization which I think we can, but there are very clearly certain characteristics that would make a good hunter.

If we’re hiring a true hunter role, then you want people who, for example, are okay with people saying no to them and will not get crushed. You want people who are okay with being self-directed because a lot of times they’re working from home and no one watches them for a whole day. So, they’re going to be the kind of people that wake up at 8:00 and just go to work. They don’t need someone standing over their shoulder. There’s lots of other people that just don’t have that and they can’t motivate unless they’re on a team and they’re sitting in a group of people.

I would say for every person here it’s very important to know that about yourself. Are you a hunter or are you gatherer? In our firm, what do you think about yourself in the role and to find the right role. I’m always amazed, actually, at how many people I see are very far on in their career prospects. They don’t have a huge amount of self-knowledge about who they are, especially on the sales side. I’ve found, sometimes—I don’t want to generalize too much—salespeople think about it as a special skill and magic, like, “Oh, I can sell anything to anyone,” type stuff. I tend to think about things personally. I may be more cynical, but I tend to think about it as a lot of hard work. Most people, if you work really hard and are a smart person, you could be a great salesperson.

Now, you have to have certain skills but that’s why you hire amazing leadership to train those skills and that’s why you have great technology is to make sure that you don’t miss your steps. Teams can supplement so if you’re not wonderful demos, you could have teams that have demos done by someone other than you. You cannot replace intelligence and you cannot place hard work. Those two things I have found for every role but very much for sales. The people who think, “I’m such a hard worker but I really got this, that people really like me,” that scares me a lot.

I’ll tell you something, people do like those people and it’s easy to fall for that. You’re sitting in an interview, they get you talking, they sell you, and by the time you’re done, you’re like, “Oh, I love this guy.” Then, someone will say, “Oh, great. What were his metrics?” I’ll be like “I didn’t even ask.” It didn’t even occur to me. You got to really hold yourself resolute. Again, the more objective you can be at all processes, all parts of the process, the better. Especially something that’s more artistic like sales.

Jono: Similar to that, one thing I’ve noticed in in building sales teams, I’ve probably built up to a 10% sales team in the past. Well, somebody might be a really good sales person, with a lot of experience and national lead at LinkedIn or something like, that was just a total rock star, came into an organization that I was running and really did not perform well. One thing I’ve seen is that some people are amazing salespeople at a particular type of environment or a particular kind of product-to-market, and they’re really bad in other markets. As an example, this guy from LinkedIn came in and he turned a $5000 customer into $100,000 customer, which was I was pretty excited about.

That was the first six figure deal we closed in and he did it remarkably well. It was all front-loaded, we had all the money in within three months. I’ve never seen anything like that before. I was just excited to have a $5000 customer. The truth is, he actually was a horrible fit for our organization because we shouldn’t be selling six figure deals. We’re not set up for it. We were set up for small businesses and somebody that’s kept paying $100,000 is looking for something very different that is somebody paying $5000.

We were paying for leads to come in that what I considered to be fairly warm and he considered them cold. I just couldn’t understand why but I realized that he was a master of taking a $5000 deal and converting it to $100,000. And he didn’t want to do anything else. That’s the type of organization he needs to be in. I’m just wondering, can you guys speak to that at all and what are the type of salespeople? Because I have a feeling you might all be looking for different kinds of people. Can you talk about your ideal type of salesperson? I think there will be something to learn from hearing the differences.

Cheryl: Absolutely. I actually have three teams. In a sales team, I divide up function based on specialty and within those teams, I actually further divide it into industries so that they specialize in a certain field. Simplifying what they sell to ramp up and help on board and get them going and ramp them up faster, we can always cross train later but let me get them having some success and excitement quickly and help them really learn something.

My first team is new business, how do we help those and again our competencies if your to do personality or competency-based interviewing. There are certain characteristics I’m looking at that I think make a successful new business individual and that might be different than another role. For new business, you’re looking for specific things on how they can relate to customers quickly. Again, I agree 100% with you. I look at their organization and follow-up on their statistics because those are super important.

In any business, when we deal with a lot of volumes—small and medium business is our niche—that is volume and it takes a lot. In sales, it’s not your first contact that’s going to get the sales, it’s building trust, it’s having follow-up, it’s putting the rigor in the work into it to prove you’re worthy to earn the business. There’s a lot of work that’s needed. Hard work, diligence, and respectful communications are going to trump someone that just knows how to do it really quickly but falls later. I look that on new business.

I also have another team that just does renewals. To your take, once you take an existing customer, focus on relationship building. How do they build relationships? Do touch points mid-year. Focus on retention to be able to retain and grow that business. How does my revenue survival rate go up to be able to support? What is that experience look and feel like? They might not be comfortable reaching out to the customer but an existing customer can definitely build a relationship.

My third is my account management team, which is a lot of customer service. It’s being able to support our chat. What happens when a customer calls in? How do I de-escalate a frustrated customer, to turn them around to be a good customer and that’s a different person? We specialize our team based on the different functions to be able to support what that looks like, interview differently and really gear what those questions are, and what I’m gearing it towards to help make sure that person is right.

It doesn’t matter what the role is. Our guiding light is our culture. We spend a lot of work on culture, defining what is that, what are our top values, and it doesn’t matter whether you’re a full-stack developer, whether you’re on our marketing team or product team or sales team, what those values are resonate across the whole company.

We actually interview and rank how they do against those values to make sure that they’re fit corporately for us to be able to make sure that they can grow. For me as a sales team, I don’t just look at where they are today, I look at do I see them moving past the role they’re playing for. Because if I’m going to hire someone, I want someone that’s going to grow with my business. If you’re applying for a new business role, I want to know what the role is after that and how I can further develop someone to get beyond the next role. I want to be able to see someone that can help build our business and be able to grow with us as we bring on new people.

Man: […] average deal size and sales things? […] put this in context?

Cheryl: Absolutely. In my space, we sell commercial insurance and we do it through digital platform. We ease for any small-medium business, how do I really streamline, respect time for my customer, and my internal team, to quicken that process and make it super smooth, but add the quality that we need to make sure those questions or underwriting algorithm, is all put into some intelligent software. Our deals, you can actually buy online with some of them so they can be five minutes and some of them can be a couple of weeks depending on the complexity. Better specialization in small-medium business with a lot of volumes.

Man: The deal size?

Cheryl: I’d say my average deal size is probably $2000 approximately. On a lead volume, we hit $500,000 last week for the first time. It gives you a perspective of size that the team’s handling.

Bram: My sale cycle is somewhere between six and nine months on average and my average deal size is probably less than $100,000 in that area. It very much varies and depends, et cetera. Ditto, like almost every single thing you said, it’s crazy. We have three selling teams also. We have a new logo as our first team which is a straight up hunter role. Then, we have what I’m calling our upsell team, which is customers that have one of our products but not the other major product. We have two big products, one of which you have to have first, so up-selling the second product to that first customer which is a very different value profit, a very different selling positioning.

The main difference is this. If you’re a new logo person, the vast majority of your time is developing trust and finding people who will talk to you. That’s a very hard thing to do. Until you are able to give a demo, that’s 90% of the value add I would argue. Once you’re able to give that demo on the new logo side, they’re already at a point where they’re interested, they have a need, they made a decision to buy a product. People are pretty excited by the time they get past that demo stage on the new logo side.

On the upsell side, the demo would be like right at the very beginning of the engagement because they have a relationship with the company. Why wouldn’t they see a demo of other products that has nothing to do with whether they might buy, they’re not putting any money out, and they already have the trusted relationship. You’re not building trust, you’re not building rapport, a little bit rapport, but not a lot. It’s literally completely different. I would say, if you put in a logo person on the upsell side, they could scare away customers, they be maybe a little bit too aggressive sometimes, not always, but sometimes.

The other way around, especially if you put a primer on a new logo deal, they’ll never get the customer. They’ll never do the cold calling. Again, it’s very interesting how many times you’re sitting and talking to candidates and they’ll say, “Oh yeah, I could do either.” Maybe that is true for some people, but my experience tells me it’s not.

Again, for everyone out here who’s in their career in sales, I’d be very interested to know how many people have a really good understanding of whether they’re a hunter or a farmer, whether they’re pursuing that, whether they’re only looking for opportunities that are similar to where their skill set is, and whether they’re really looking for the right role that matches their skill set. I do find most people just tend to look for jobs that pay money because they need to get a job and they’re more eager to do that. They’ll figure that they can figure things out. I’ll tell you, if I hire a new accountant, it takes them half a year to be productive, to get up to speed to learn the books, to learn the culture, to learn the phone system, just to be comfortable. It takes a long time.

When I was in business school, we did a study that said it takes a year on average for an average employee, but for the easiest transition I would say would be let’s say finance or something like that. The books are the same, it’s just […] are taking over. For sales, it’s at least a year, at least.

The cost of switching jobs for the sales person, especially, is so astronomical that really I think should be a lot more work put in, especially sometimes on the candidates I’d argue what the right role is. What you really are looking for and I also say that it makes people—it is a little off topic, but I think it might be relevant for this particular group—a much more compelling candidate.

When you can come in and say, “The reason I want to work for you is because I’m a hunter. I know that this is primarily how you sell and I’m okay with a nine month sales cycle. I enjoy this and that and I enjoy developing relationships. I tried being a farmer and it didn’t work out for me.” By the end of that interview, you’re like “Oh yeah, I got to take a chance. This is someone I really need to talk to,” and the opposite vice-versa, too.

The third team is our cross-sell team. Our product is structured that our customers will start with accounting, then it will turn online payments, and then we have now maybe 10-15 other smaller products forms so parents can fill out their online forms for their students, various consulting services, and much smaller things. We have right now one, although, we’re expanding that team to two or three. As we’ve been scaling, we’ve been focusing on the other two teams which is why I paid less attention to it now.

Also, for us, our account management teams and customers—we call them customer success management—that actually is not under sales. That’s a separate team for us and we don’t put any selling under that team at all. We have a cross-sell team which is effectively the selling arm of the customer success management team, which is in my client management division.

Clients would be on boarding in client management, that would be my client’s division and sales is self-evident, I think, and if you’re selling then you’re on the sell side. I want my customer success people to have a deep relationship with my customers and I don’t want any customer saying I can’t trust them because they’re just trying to sell me stuff all the time. That’s not the relationship I want them to have with our customer success.

We also have a different world in general because we have very little customer turnover like almost zero, just because the nature of our product and also, I’d like to think we do a lot to prevent that. Most SaaS businesses do, by the way just to let you know, literally 99% of them do. We just are very lucky that’s something we don’t have to do.

Man: You said you have the cross-seller or upselling teams. Is it the source of the business how you’re selling to schools and stuff? Or do the parents there, the forms come in, and that you ask, say I, as a parent have something new I need to check out?

Bram: That’s a great question. We sell exclusively to the school district. We don’t sell to the schools. We call the CFO and his or her staff at the school district office. For example, TBSB is 583 schools, so we’ll do one call for that. There are some at tech businesses that sell to the schools, private schools mostly. Jono does that. You can talk to him about that.

For me, that would drive me nuts so we had to call the big guy. We try to focus on the big guys as much as possible, but it does drastically. Jono can close a sale in five seconds, that’s unheard of for me. It just doesn’t happen. We have a huge amount of RFPs and procurement. It’s a whole different world in public school space.

Jono: Right, and just to speak to different personalities, I tried selling to districts and I absolutely hated it. I’m good at small business sales and it’s just something that I’ve been doing. It works for me. It’s just a personality thing. I obviously just stuck with what I knew I could scale because I have a history of doing that. We have no plans in going into districts. At one point we were thinking about it, I would just bring somebody else to do that because it drains the life out of me. It’s a personality thing. I don’t know if I’m a hunter or a farmer. I think I’m just a killer. I don’t like hunting or farming. I like to close.

Man: I think you answered the question.

Jono: Yeah. I like it when other people do the hunting and bring me in to shoot it, that’s what I do.

Man: You have people in the first lane here.

Jono: I want to go online forever.

Jordan: I’ll be quick on this one. In my previous role, I was managing business development sales and post sales which is, in some definitions, customer success. Every company calls it something different. What I realized was the business development was quick wins. If someone said, “Let’s get a meeting with this company,” we will get that meeting almost right away and this is CIOs, CDOs, the highest roles within the banks which is unprecedented. It was just by pure cold calling, emailing, and just a little bit of relentlessness but just keeping emails extremely short and just doing the hard work. Then on the sales side or sales cycle, to answer your question, is anywhere between a year-and-a-half to five years.

Jono: Shoot me now.

Jordan: Shoot me now and between meetings would take 2-3 months just because you’re dealing predominantly with banks. The post sales was pretty fun. They are already clients, so you don’t have to chase them down. They typically want more out of you and you can develop plans. I developed a smart community plan with Bosch, the dishwasher company—but they do many other things—and put a whole smart communities plan for them to up-sell them to much larger contracts which got sold. I thought that was interesting, but it didn’t really get me excited. It was fun, but it didn’t get me excited.

What I realized in this whole process was actually having the benefit of working all three angles was that I really like the business development side of things. That’s actually what prompted me to move from predominantly the sales role at Flybits to head of business development at Zafin because that’s what I realized what I’m really good at and what I really love is piecing things together, getting in front of people, and building as many relationships as possible.

Now, I don’t have an America’s footprint, I have a global footprint. Right now, I’m setting up an arsenal football match on Sunday with all the top CIOs of all the top banks, and I’m their best friend. That’s cool for me. I’m connecting already our company to Salesforce and many other partners and everyone looks up at me as the starting point of the company as opposed to where’s my next sale this week.

Nick: Tickets size, anywhere from $10,000-$50,000. Sales cycle, one call closed to two weeks. That’s why we’ve been able to grow so fast and I think it’s a little bit uncommon for people but Jono knows; you were in our ecosystem for a while. One call closing $15,000. I had one call close a $40,000 deal and we can do that. You need marketing to back it up. We use what I call video sales letters and I don’t know if you guys saw my marketing or whatever, but…

Jono: Go on his website, it is the best video ever.

Nick: Yeah, it’s there for a reason. We understand it takes about seven hours to get a customer. They have to be listening to us, thinking about us for seven hours. You can either do that over the sales call, or you do multiple calls. You’re chasing people down, hunting them down, sending them letters, and going to football games or whatever. I would do that if the deals are big enough, but we’ve been able to use technology to get that seven hours in with video sales letters, webinars, advertising. Then, when someone gets on the phone with us, they’ll open up their checkbook, and that allows our salespeople to move real fast.

Jono: This has been incredibly helpful for us, too. I talked about this a lot with people and I said, “Back in the 80s or 90s, early 2000s, the only time you ever saw an infomercial was if you were on TV late at night. Today, everybody can make their own infomercial and you can do it if you know how to get the traffic to that video.” One in Nick’s original point, sales hasn’t changed. It’s just the medium. It’s funny. When you’re looking at an infomercial and you’re not interested in what they’re selling, it looks like the most god-awful thing in the world. How could anybody walk that slap shop with that guy who is so ridiculous? Actually, when it speaks to a problem that you have, you’re like a fly or a deer in the headlights, because it works.

Humans work a certain way. We are not also to that personality assessment point. We work a certain way. Sales works in a certain way and that’s why every single infomercial is written almost exactly the same way. It’s a template. It’s the same template that you see on a flyer that you get because that was the original direct mailer. How does your company extrapolate the elements of a sales letter or an infomercial, and then of course speak to your particular audience that has their problems?

I think that’s really sort of the art of sales. It’s figuring out how to interpret your solution into that method. What’s the right way to deliver that message is different for different sized sales and different markets. If you go to Nick’s site, it’s a great example of a video that sells. If you watched my webinar, I literally take Nick’s template and I use it and it works incredibly well. I’d say it’s probably at this point, a good time to open up to some Q and A. I know there’s been some questions already, but we will just let you guys have at it. So, go ahead.

Man: I’ll take the first question. We are in a […] automation company, but for us showing people that these boards that people have been talking all these big companies we have that. We’re putting that on LinkedIn. The same discussion that we were just having, when people take out there, a lot of people like a lot of my peers call me and say, “Why are you guys putting so much information out there? Anyone can build it and take it.” I said, “Feel free. Go ahead and do it. What we do, you can’t do it or the quality of product.”

The one thing that I just heard from you, Jono, is the infomercials. It’s information for us. The thing that we hold back is what is the ROI and what is the solution? Much more details on the solution. Do you think that we should be putting that information out to the people, too, that this is a $30,000-$40,000 solution? You should be buying it from us and this is the ROI.

Bram: Why didn’t you […]?

Man: Why didn’t I?

Jono: The pricing in your marketing? You’re saying, don’t…

Man: The ROI specifically.

Jono: Oh, okay, yeah.

Man: Obviously, I’m not as smart, so I look to people like you. And people like you say, “Why are you putting this first board on LinkedIn and they get a free video coming up with […]. You have that on your website and then you have it on LinkedIn these recordings. People will find these solutions and they’ll start learning.

Bram: Sorry, but just to make sure I understand. What you said is, […] puts it up on the internet, and everyone told us to take it down, but we said no, you try to build it, go ahead.

Man: Yeah.

Bram: But then you don’t include the ROI, but for the same logic.

Man: But the thing is, so many people tell you, you get scared. I know I’m not the smartest, I look up to people.

Bram: I’ll only say this probably speaking, okay? I’m not […] but I will just say this. It’s unbelievable how many people think they know anything and it’s really even more unbelievable how few people know anything. If anyone knew anything, then they would be doing what you do. They don’t and they don’t know. People generally give advice I think a lot of times to make themselves feel better or to talk to themselves, not talk to you. In general, I don’t know about your specific issue, but don’t listen to anybody.

Jono: I agree with that. We put a lot of free information up. If your solution is easy to copy then there’s not any value in it anyway. If you can give part of it away and you’re worried about getting stolen from?

Man: I’m not worried about the current […] solution are better than what we build and put on the videos, but then we held back and now I’m regretting that after 2-3 weeks, that we put this […] here. I have seen a lot of people seeing it, but I’m not getting these calls.

Bram: […] that.

Nick: Yeah.

Man: We made a mistake there.

Nick: With the ROI justification, it’s more of like a bottom of the funnel conversation. First order of business, you got to make sure that they’re interested in the problem that you’re solving. Then when they’re ready to pull the trigger and they’re looking at the price, and they’re looking to justify the investment, that’s when you can talk about ROI. But as far as top of the funnel stuff, you really want to attract people that are interested in your solution. Put as much information out as possible. We do that, I put out a lot, but they still can’t piece things together. You have to be a customer to get the actual cadence.

Jono: I would say that one of the principles of this form of marketing using content or long form video like webinars or VSLs—video sales letter—is you’re showing them the what? What is it they should do to solve their problem? But what you’re selling is the how. In ours, we sell a hands-free enrollment marketing solution, it’s a complete marketing funnel top to bottom for private schools, and my webinar breaks down in detail a case study of everything that we do for our clients with examples.

They sign up because they want to learn what it is. If they have somebody in their organization that could take that, go test it, play with it, and try to figure it out for themselves, then great. I happen to know for my market, they don’t have that. It’s going to be a very, very edge case for them to have that.

What I’m doing is I’m positioning myself like the expert, because I have all these case studies from customers that are successful and I’m giving them what seems to be the secret sauce. The real secret sauce is, we’ve all spent thousands of hours doing it and building the solution. They’ll never going to be able to copy that ever. They don’t have 3,000 hours to sit. They don’t have any time. They can barely get the hour to watch this webinar.

That’s the next point. If somebody can easily copy it, and if it’s that easy to copy, then you have to think about if you’ve built something of value. If it’s not, then you can show them all the information; you’re totally safe. That’s been my experience and seems to be theory that works.

Jordan: My advice on that and I think what the number one problem on sales is that, well there’s two. One is, I go into a website and I never know what anyone does anymore. It’s like, “Please boil it down for me. Let me know what you actually do.” The other is, what information to include. Don’t try to sell the whole company, the primary and secondary advantages, and everything else that comes with your product. Just pick your poison, if you will. and stick to it. Keep it nice, short, and concise, and the rest will come. The point is that for business development, our goal is to get a meeting.

The initial discovery meeting, you’re just trying to gather a couple of things and get to the next meeting. You don’t try to oversell. I’m part of the transformation team at Zafin, and really, it’s just about really boiling down our message of all the key challenges in the banking world that we fit and one of the things that I’m providing advice is leveraging the Salesforce methodology, which are things like the first slide. If you look at any slide in the history of Salesforce, they open up with an industry transformation, but what’s the table stakes of someone actually carrying about your solution? Get the emotion out of them, then talk about development. Why haven’t they’ve been able to deliver on the challenge that they have and then go in the promise and in other things.

I highly recommend googling Salesforce methodology and how they present their solution. They’ve stuck to their guns for the last 30 years since they’ve been in existence. The point is, also look at people that have done it and done it extremely well. Even though Salesforce or a company like that has no relevance to what you do, just take their learnings that they’ve stuck with their guns and they’ve had this very simple process and how they communicate their solution.

Jono: Yeah, another question?

Man: […] about your comp plans, your sales […].

Bram: We got a base salary and then we commission on top. The rates increase once quota is hit. There are three buckets, probably speaking of commission until I think it’s 70%-100% and then above 100% with no upper limit on top. I guess it depends, but that is […] it helps my salespeople sell. Infinite amounts of software and make infinite amounts of money behind it.

Man: Where do you set your quality? How many people usually meet their quota?

Bram: We’re too early in our experiment right now. Historically, a lot. A high percentage because we had very few salespeople, but going forward, now that we’re expanding ourselves, I don’t know if you were here from the beginning, but we’ve just built that whole sales team from scratch basically, TBD.

Nick: Are you hiring in Toronto?

Bram: Yeah.

Nick: What’s your base? What’s the OTE in Toronto that you guys have found that works?

Bram: I don’t want to say it publicly because it’s going on YouTube. We don’t publish that information.

Man: Can you give a range?

Bram: How wide should the range be? Between 50-100, I can tell you that. Our base is between 50-100, our OTE should be at least XX the base, I think.

Jordan: We’re somewhere between 50-100. Based on what I know from my previous role which is we’re pretty much selling the same roles within the banks, I did the math actually today. It’s $92,400 per year on top of their salary. They’re very achievable goals. I keep telling my guys, we have a really amazing comp plan that we’ve created.

The one thing that I’m adding on top of the comp plan and it’s really, really small but going back to my Trello is when you have stand ups and all these meetings. No one really cares about the next guy, because in reality they’re in competition. They’re always trying to look good in front of everyone. What I’m implementing is very small, what I call a team goal. It’s not for myself and I made that clear that if everyone hits their quarterly goals, then there’s an annual bonus involved.

It’s also being creative. You don’t have to set a high amount, but now when we get into our stand-up meetings, the other person will actually give their guidance as to what works, what email formats, or what messaging, all these sorts of things, and they’ll actually help try to get leads if one person is falling behind on their quarterly quota. It’s pretty cool to see that you could shift the psyche on your team members pretty quickly.

Cheryl: On our side, we have a salary and then we have bonus structure. We’ve done that bonus structure. We do also have a team target. We’ve got a bonus today. We’re looking at a commission structure for next year but it’s been bonus structure as we’ve grown and tried to play with what that looks like.

Again, our sales process is much faster than yours to be able to support what that looks like and to be able to scale properly. A little bit different business model and ours is a little faster, a little more high volume, and repetitive. Taking a look at what that is, it’s a bonus structure. We have I’d say the biggest incentive and reward on our team as we rolled out team leads. That has had a huge impact to motivate the team. Because we’ve grown so quickly, we now have taken our top performers and made them team leads, which has become a player coach model. Whereas a player, they need to be top in what they do and they also coach a small team to be able to lift the individuals in their vertical and where they specialize. It has helped with on boarding and ramping quickly. It has created a big motivation and then we gave them a little bit of a team budget where they had some budget to do what they wanted with it.

Again, this is inspiring them to figure out how do they use that money and it’s been more effective to give it to them and say, “Now, figure out what you’re going to do to motivate your team.” That dollar value, they could use it to take the team for lunch. They could use it to go for beer and wings. They can go to play pool. We had two of the teams that had a competition between each other where they put 50% of their budget on the line for whoever could bring in the most revenue.

It has been a lot of fun to see how they could put their creative juices together to figure out how do they use this budget for some fun and it’s had a much bigger impact than probably a commissioned plan. I know that seems crazy, but it drove some great results, and I think it elevated the performance of the team, but also elevated the job satisfaction because they felt like they were building something, and it had a huge impact for us and the team morale. And I think it helped fit into what culturally we’re trying to accomplish, to have them really take ownership of their spaces.

Man: […] Do you sell someone and then they make sure two months later, there’s not much value in the sale. Have you ever thought about […]?

Cheryl: In my space, it’s an annual contract. The customer doesn’t leave after two months, it’s really rare, and most of the payment’s upfront for the year. For us, we don’t have that challenge. Again, I have a renewal team that owns the renewal and the survival rate of not only our policies but survival rate on the revenue, on the upsell, cross-sell upon that renewal. We have a fairly sticky business where we haven’t had the issue of the churn that it created a good motivation factor on bringing in new business.

Nick: I’ll speak to that. We have a pure commission structure and it’s been good. Our guys make a lot. Our top guys make about $25,000 a month, but it’s purely commission. We started bringing on newer folks. We started them off with a little bit of a base but I was always trained in commission only sales where, “Will you kill?” sort of thing. It makes them really, really good. We lose them fast if they’re not good, but once you end up being good, they make a lot of money and they do well.

Bram: I agree that if you do commission-only, you tend to get really hungry, self-reliant people. What worries is it seems to me like if you have had 10 years of success as a sales person, you’re ready for a switch, and you have a family and stuff, unless you have a big draw, people need that money to live. Wouldn’t you just say that some of the best sales people in the market wouldn’t come to you because it’s commission only?

Jono: If you don’t have a track record, then it’s going to be difficult to do commission only. The way that you get the best sales reps is if you can show a guy who’s making $25,000 a month. You’re like, “Hey, do what he does.” You’ll attract the best guys because they just want to make more money. 

Man: How do you […] base plus the commission? I don’t need to take that kind of a risk in my career now that I’ve […].

Nick: That’s true. They’re in their 20s, right? We’re finding people in their 20s. We had someone in their 40s. I don’t know. How old is Jake, probably like 43? Something like that. It was a lot of pressure but he didn’t hit the numbers that these young guys were doing. It seems to work. Our guys are pumping out good numbers. Our one guy’s tracking for $200,000 this month in sales and then he’ll get 20% or 15%. It keeps people going.

Jordan: Yeah, I think I tend to agree with you. Sales is in such high demand especially here in Toronto. I don’t know the quota I read the other day, it’s the number two topic on LinkedIn. I think salespeople are in the buyer’s market. I think it’s a buyer’s market. If you’re going to get anyone who’s worth their salt, they’re going to go for salary but it would be nice to be able to […].

Nick: I’ve found that people that want salary, they’re not even that good anyway. I’ve had that experience. They’re like, “Oh, I want this. I want that salary.” I’m like, “Go. Go do it. Go get a nice salary.” This is what I found out. Our best reps, they’re the ones that put in a resume. They bug me on LinkedIn. They bug on Instagram. I don’t respond to them for a month. They keep bugging me. They might even buy our product and then they’re just like, “Are you ready to go?” They’re really bought into the whole business. Those are the ones that I found that are really successful.

Man: I will follow you on LinkedIn.

Nick: Yeah, sure.

Man: I’ve also seen your website and I wonder where you get those […] from. You’ve got that […] system, so you’re talking about […] seven hour thing, and it seems like you’ve got a commission only approach, that you built a system ready for that approach, right?

Nick: Yeah. It’s true.

Man: Rather than saying, “Hey, […],” I won’t pay to do that. Where are you on this? I couldn’t […] and say, “Hey, look. […] commission. You need it and I provide with a brand that’s going to…”

Nick: Yeah. Here’s what happened. The reason why we have the Lamborghini stuff with that, it gets a lot of attention. I did a case on it. You run an ad of a freaking green Lambo in there, the clickthrough rate is going to be really high. Also, it fires up the young people to come work for you. I don’t even drive a green Lamborghini. I have a black car. It’s not as flashy. I don’t really like that stuff but it attracts the people that we need to attract.

As far as getting started, I didn’t always have the brand, but I was just a dog in the trenches. I got to $50,000 a month just by doing outbound prospecting and closing over the phone. I would just be hitting link. I was doing door-to-door on the internet. I was just hitting my messages every morning for 2 hours, just […] only $3 a day, and then I would close it on the phone.

I would just show that sales. My first sales rep was Joseph. He came on and I just showed him the numbers and I was like, “Dude, if you can do what I’m doing, give it a shot.” I didn’t even pay him any salary. I was just like, “Yeah. I’ll give you a percentage.” He saw me do it. I led by example.

Man: Was that […] to getting onboard with that as well?

Nick: No. Basically, the key to attracting really good salespeople is you just lead by example. That’s what I found. If you’re just a stone-cold killer like Jono was saying, people are going to want to work for you. They’re just going to be like, “I want to work for this guy.”

Bram: Everyone’s who’s a salesperson, just put their hand in the air for one second. For anyone here who would currently take a job that’s commission only, can you keep your hand up?

Nick: Okay. Here’s another question, who wants to make $25,000 a month? Right?

Woman: These are all of you guys. How much more do you value someone who is young and hungry but less experienced, […] very passionate versus someone who is super experienced but then, they also want some stability?

Bram: Young is not the right adjective, I would put on it, but I would say the following. Historically, we used to have a model which was find people who I thought could figure it out and do it and the model sucked. It didn’t work. It was impossible to replicate. There was no consistency to it.

People used to say to me, “Bram, we need to hire in the territory—local—and you need to hire people who have ad tech experience. You need to hire people who have SaaS experience.” I just, “No, you’re not right. You are all right.” The more I have moved to hiring people who’ve done exactly.

Jordan: You didn’t go with your gut on that one.

Bram: No. Definitely not. No. By the way, I’m a pretty terrible manager if you just blindly close your eyes and only trust your gut on every decision. There has to be a healthy balance. I would say the more we’ve been able to add objectivity to it, the better.

People who’ve done it before, you can ask them questions about it and they can tell you. Where if they haven’t, you just have to trust your gut, effectively. I would argue that it might make them better experience. I don’t know, but it certainly makes it easier to determine whether or not they have the track record, if they’ve done it before. If that makes sense.

Nick: I agree with your point. I find that if you get them too many experiences, to much of an investment, it’s too risky but if they’re too experienced, they’re difficult to coach. There’s a little bit of a sweet spot in there. Also, you don’t want them to be too entrepreneurial either because then they’ll go out and start their own business after three months. You put $75,000 into them.

You were speaking about the opportunity cost and the cost to ramp. We spend $20,000 a month for advertising per rep. Three months, we’ve invested that advertising budget into them and we lose them for three months. It’s really costly. I think there’s a sweet spot. I definitely agree with you on the little bit of experience, for sure.

Jordan: I think more important is having people on your team that have industry-specific knowledge. What I mean by that is somebody who’s been on the other side. I don’t know if you’re in warehousing, you’re selling robots to warehouses.

Man: We sell […].

Jordan: All right. Okay. Maybe someone who works at a warehouse.

Man: It’s someone who would be working out […]. Someone like where Cheryl’s been. We have come to that. In fact, I have someone on Thursday, tomorrow is his first day with me and he comes from insurance sales. The product that we built works in insurance […]. I’m teaching what this […] does and ask him to go through the product […] before he […].

Jordan: Having an industry with knowledge. You’re speaking to the person that you’re now selling to, you’re speaking their language. You know the problem that you’re really, truly solving. That, I find, is more important than age. An old person will bring knowledge, maybe be a little lazy, come in at odd hours or leave early. You might have a young person as just to go-getter. I think it’s a healthy balance as well but more of the knowledge is what I’m looking for.

Man: I’ll add something there. Part of my job is product development. […] I’m hiring. These are students who are either international students or people who are coming […]. We are not paying them, part of them. There’s a part of […] like or four people. The only thing that they have is […] so hard in the market at the same time working for your organization, that they are ready to put those three months with me. […] all of them. You guys stayed with me for more than a month-and-a-half. You will be getting your fair […] number, but this is on the top side of what Canada immigration says that I can sponsor to the  immigration to this country. There is a top 5% of the pay for these people who bring three numbers. These are very hungry people […].

Bram: On this point, I would say this. We have found a lot of great success hiring new immigrants to the country. In general, hiring what, I don’t know if I’m going to say this politically, candidates that have had a harder time getting a job in more traditional channels because I find that a lot of people who are responsible for hiring are not wise people. They use not data to make decisions. You’re able to find people who might have an accent or might not be able to express themselves super well within the first month of them coming to the country but they have 20 years of relevant experience killing it.

Not only that. someone who we just hired recently has a wife and kids at home, they had to make a damn living to bring them over. There was no failure in this person’s option. The drive was there. I found, in general, the people we’ve been able to hire like that have had a huge amount of respect, they love to learn, they’re very appreciative of the opportunity because people have slammed the door on their face quite a bit and it must be a very disheartening process. By the way, we hired them because they’re great, not for any other reason. It’s been really wonderful and we’ve been able to do that across the organization. Less so in sales. True in sales but less so in sales but in technology or product.

Man: […] 25 or 20 that’s always the […]. My wife, she’s the founder and she talks to them. One thing that we ask them is your attitude towards other people. We don’t ask you what your technology supplies or anything but there’s something so new, we will teach you, but if you don’t have the attitude, you’re not a go getter. I have people who work Uber on weekends and they’ve work five days with me […]. I come […] seminar. I won’t say what happened with those products there, but […] took three months to built there, my team […] seven days. This guy who drives Uber on the weekend was so hungry, he spent all evening studying and then coming and working for me. I don’t tell them to […]. I think the same thing with people […] hungry and you say, “Yeah, you want […] work like me.”

Nick: Yeah, but the whole Uber thing, I want them focusing on their job so I’ll float them. I’ll give them a draw so that they don’t have to do that. It’s the same principle. They’re really, really, hungry.

Bram: We all try our best to create replicable and scalable activities on sales especially. I have found that no matter how much that is true, still the 80-20 rule applies. My question is, on your various skills of your organization is that true? How much of your sales are made up by the top 20% salesfolk?

Cheryl: I would say ours, we’ve created a model that’s scalable and we have a stronger team approach to bring everyone to that level. I’d say, “Give it more of a 50-50 where we are today, trying to bring it closer to the 80-20, the opposite direction.” I’d say that we have created a process that’s really onboarding and bringing people up to create it for success which is unique because in past roles, I agree with your 80-20 rule but I’d say that we’d shifted it.

Man: […] 50-50. You’d say the top 20% of the organization […] 20% […]. Is that what you’re saying?

Cheryl: No. I’m saying that it’s more than that that’s contributing to the amount of sales. I’d say that if I was to look across the organization on the sales level, we have more than 20% of our sales people bringing in their targets. Does that make sense?

Man: Okay. Yeah, I think I understand.

Jono: Just to give you some context, I used to hire college co-ups. Every 4 months I’d hire 10. It works in this market but within a week, I would train them. We have them selling for the next four months and if I was lucky, I could keep them for eight months. It was exhausting so I wouldn’t suggest it for anybody. If you’re good with selection and your training program and sales process is good enough, everybody was profitable but always, I saw the […] play at. It was always two of them made the majority of the sales. You want to keep on harvesting that top 20% and then move them up. I see it in hiring. I’ll bring on five, I’ll keep two. They’ll get past the first training month.

Man: Yeah, we saw the same thing.

Nick: Our script, I agree. We have a script and a process that we get everyone closing to the same percentage in a week because the script is 15 pages.

Man: It always […]?

Nick: No, there is but it’s not where you think it is. We get everyone closing to a certain amount really fast and the same time frame, but where the 80-20 thing comes in is the people that keep going. They’re durable.

Man: […] to deal with it, by the way. I […] annual sales number and how much is 20% of that, how much of that number is 20%?

Nick: We have that.

Jono: I don’t think you can get away from it.

Nick: No, it’s 80%–20%. It’s like they’re in the 80-20 thing but it’s due to just people that just keep going.

Man: I was hopeful that wasn’t the case but I thank you guys.

Cheryl: I think what I’m trying to say is in our business, I think it’s more than 50% of our people bringing in 80% of the business. I think we’ve got a higher percentage of contributors. Don’t get me wrong, we still have those that you’re ramping up. I have a higher percentage of contributors compared to a traditional sales model.

Man: I bet if you went into that […] 50% […] 80-20 ratio.

Bram: Well, maybe, but it doesn’t matter. If you can get 50% of the people to be contributing in a meaningful way, I guess I was just wondering if […]. So, here’s my question.

Man: You’re better off […].

Bram: What about IBM? Or Apple or whatever? Are there businesses out there that have figured out how to get 80% of the people contributing?

Nick: We have people, everyone’s contributing but they’re the superstars. They bring in twice as much as everyone else.

Bram: Isn’t the job of head of sales effectively drafting from the top players? Can you take a strategy that basically assumes most people are going to not perform? You really are just looking for those people that are really out performance if they’re not shift and move on? It’s not the way anyone approaches their job, though. Everyone approaches their job as, “Well, I’m going to hire and create this big team. Everyone is going to hit their number. We’re setting […] point where everyone will be successful,” but in reality, I don’t know.

Nick: No. We built that into ours. I came from door-to-door. When I was 20 years old, I worked for this door-to-door sales thing when I was in between semesters. I thought that was normal, 80% of people would just turnover. I’ve always prepped for that. If we bring in five, we lose three and have two stay but we lose them quick. That’s what we try to do.

Cheryl: Because you’re 100% commissioned.

Nick: And we have this test. Have you guys ever heard of the Peloton bike? It’s like an exercise bike. It’s the one that you can output wattage. I think this was before you were there. For the salespeople, if they hit 200 watts for 20 minutes consistently, they’re hired. We had people competing. We didn’t really enforce it but we just wanted to see. Obviously, we couldn’t enforce it, but I did it, so I challenged everyone. Those types of  fun tests, you can learn a lot from your sales team.

Jono: Do you have a question?

Man: Yes. Thanks, Jono, for having the event. I remember the first […] more of a surrounded pizzas, so pretty impressive. Thanks for all the […]. Cheryl, you talked a little about making sure your staff has the most important thing […]. I think you said seamless work list or seamless workflow available to them. And you mentioned the part of sales […]. Maybe you could speak a little bit about  the tools and how you integrate them? I think sometimes there’s so many tools now that it’s like, what is the next greatest tool? I think there’s some consistency across […] tools, but I don’t mind hearing a little bit about—

Nick: Like the stack.

Man: Yeah. What kind of tools are you guys using? Maybe […] list of general, what  tools are you finding success with narrowing down the noise and letting […].

Cheryl: From our side, we don’t use traditional insurance tools. We consider ourselves a tech software company that happens to sell insurance. We lead with technology and the efficiency of that technology first and the product happens to be commercial insurance, which is very different. Don’t use all those epic systems and if anyone comes from insurance, some of those are old tools.

For our CRM tool, it’s Salesforce and we’ve adapted that to be able to really fit the niche of what that looks like. For email automation, to be able to create a cadence with timed proper messages on follow-ups, we use something called Mixmax. I’ve tried a couple of different tools. I find Mixmax has a more intuitive interface to it.

Man: […]

Cheryl: You could use that one. SalesLoft we used in the past. I find Mixmax has a more intuitive and customer-friendly face to it. It allows you to white label it so you can put your own branding and logo on it. It has different pulls on it.

Jono: Is this for email marketing automation or sales emails?

Cheryl: Email automation. We do it for sales emails as well as renewal messages because in insurance you have to reach out for renewal, certain timing ahead. It allows us, if they don’t respond with certain questions, it has an automated second message to do follow-ups. As soon as they respond, it stops them from that cadence. All those messages come back into, we use Zendesk if anyone’s Zendesk, to be able to support with that ticket system looks like, to be able to organize.

All of those tools feed into a Salesforce report where that reporting metrics can show the last time we touched that customer, who’s responded, whether they’re on a series of cadence messages. They’d come off so that we can manage that workflow to be able to support, prioritize who’s the next one you’re going to mainly reach out to and why.

Man: And then you said, […]?

Cheryl: Absolutely. We can actually see if they’ve opened, if they’ve clicked. All of that is recorded in Salesforce underneath the contact to be able to take a look at what that is. Zendesk also records all of the phonecalls. For insurance, it’s good to have a recording. It’s great for training purposes, to be able to hear those phone calls, be able to give proper coaching.

Jono: One question I have is you must have additional team members that focus on optimizing and tracking that. Obviously, your salespeople are busy using it, so is that you? Who helps you build those systems, optimize them, and maybe split test what emails work better? What’s that role called and how many people work on that?

Cheryl: Great question. I’d say I set it out myself but it was a lot of work to do it and I am probably not the best person to do that. We now have a sales operations or someone that helps with all those metrics. I now have someone that sets up some of those dashboards and reporting for me now that the team is larger. I also have the benefit of we have we have full stack developers on our floor.

We build our own software tools because we’re a software company. I now involve them on some of these integrations to be able to make sure tools can integrate and feed into our website to be able to really support that experience including our online chats and have those tickets feed in. We have got some automated shortcuts for answers that we’ve built in to simplify that whole process and to be able to make it a more consistent experience.

Jordan: I have one that I haven’t used yet but we’re ramping up our customer list or our prospect list to launch in January but actually do a one-day test in November. It’s called ConnectAndSell. I don’t know if it’s unique but they basically do hundreds and hundreds of calls a day. I don’t know if it’s robots or if it’s people from this company that makes the calls. Whenever they get somebody on the line, it transfers over to your business development team.

I think it’s pretty cool considering you probably spend about 90% of your time, at least, trying to connect with companies. Built a separate business to fix this problem but I think that would be really cool from trying to get in front of people, I think, still connecting on phone at any industry. I do it at the bank level with my team and it works. I presume it would work for any product under any industry.

Nick: I can give just the basic stack because this is what we do for our business. If you need landing pages like ClickFunnels or HubSpot, Act! of campaign for email automation. It’s reliable, It’s cheap. I like for my CRM. HubSpot’s okay. Salesforce, I don’t really like, it’s cumbersome. Jotform for quiz submissions, Calendly for calendars. I use Facebook Analytics to track my funnel stuff, Google Analytics for redundancy, and ZapHere to tie everything together. What else do we use, Justin?

Jordan: Just don’t do email tracking. You’ll go crazy.

Nick: Zoom for calls. We use GoToWebinar for webinars, some of that, but Zoom does all the recording stuff.

Man: […]

Nick: We got 40%. Actually you have to be a customer, but want to sign up? 40% off, bro.

Jono: There’s 20 options for each one of these things, so it’s really annoying when you’re trying to figure out which one to use. We have a totally different stack and then we try to get analytics happening and some of them play nicely with the analytics, some of them don’t. It’s really frustrating. One thing that was just a remarkable change in my life was I used to for the calls. Then when we switched to Zoom, it’s literally like their commercial says—it just works.

I sell to predominantly middle-aged and up women that are teachers that are running businesses. They’re not very tech-savvy. They don’t use these things very often. It was always 15 minutes just to get them onto the presentation. I switched to using Zoom just to try it and they would just show up and they’d be there.

Nick: You want to hear a funny story about Zoom? We had a sales guy and it was his first demo and he didn’t know how Zoom automatically started the video. He has his script there. He’s eating a sandwich. There’s three people in the conference call and he’s just eating his sandwich and just motoring through the script.

He didn’t know the video was on. One of our other guys was watching this guy sell and go. I’m in the same room and he’s like, “Nick, you’re not going to believe this guy. Look what he’s doing.” The prospect was like, “This guy is the most confident guy.” He ended up getting a deposit. You got to be careful with Zoom. Make sure you know if it’s on video or not.

Jono: You don’t want a sandwich to be part of your sales process because you’ll get pretty stuffed pretty quickly.

Nick: What’s that?

Jono: If you’re always using a sandwich to sell, you could get pretty fat.

Nick: Oh yeah.

Bram: I would just add two things here quickly. We use a lot of the names that I’m hearing up here. I tend to be pretty skeptical and cynical on technology in general and think that a lot of people would be like, “Oh, we wouldn’t be selling but we just need to turn on three more systems that cost another $100,000.”

I’m thinking it actually affects top performer sale. It does get much better visibility and help people out a bit when you have a good team and motoring the ads and tools adds a lot. I would say we implemented RingCentral company-wide for a video chat and all of our conferencing. I am a convert, I just love it. Now, it has just shortened the distance from all of our people who work at home. The head of sales run a weekly call for half the organization by now. Everyone videos in and everyone can see everyone else. It’s just so nice and so easy. That was a big one.

The other one, we’re just starting to use across the business’s teams by Microsoft now for chatting and communication. That helps because what we found is, a lot of people use their email even with customers. You have these strings and then someone would leave the organization then you’re like, “Where was that whole thing? Oh, we lost it a long time ago.” You don’t want that to happen.

Jono: Okay. I think we’re going to end it here, but obviously, we can stay. There’s lots of pizza and drinks, leftover coffee, anything you want. Any of the panels want to stick around and […] and answer the questions. Please give the panel a round. Thank you so much, guys. I’ve learned a lot. I guess we can all find you guys on LinkedIn and what have you. Thank you, everybody for coming and we’ll wrap it up.

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