Ep. 62 – Lessonly President & COO, Connor Burt

Hiring people for sales and training them is a huge task for any growing organization. Conner Burt, the President of Lessonly, showcases how their brand has become the powerful simple way for teams to learn and practice like never before. Conner has been responsible for growing Lessonly from 0 to 750 clients

Hiring people for sales and training them is a huge task for any growing organization. Conner Burt, the President of Lessonly, showcases how their brand has become the powerful simple way for teams to learn and practice like never before. Conner has been responsible for growing Lessonly from 0 to 750 clients and over 2 million learners. In this episode, he shares the core of their model, its setup and scope, and their long-term plan. As a growing company, Conner also talks about their hiring process and the importance of getting their staff in a smiley environment and a fueling culture. He also discusses the tools they use for scaling Lessonly as well as the big lessons he learned from working with other key leaders.


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Conner Burt is the President and COO at Lessonly. He serves all of Lessonly’s quota market teams and has been responsible for growing Lessonly from zero to 750 clients in over two million learners. As a first time entrepreneur, he used his prior adventures at ExactTarget and a background in Division I college athletics as a coach and player to guide his philosophies around building worldwide teams. Conner, welcome to the show. 

Thanks, Cameron. It’s great to be here.

Tell us so everybody’s clear what Lessonly is. What is it? How does the business model works?

We have the privilege of helping primarily sales and customer service teams do better work with our training software. The idea is you think about a new or an existing seller or a support agent. These customer-facing teams that are interacting with brands every day tend to be the hardest to train in an organization. We’ve purpose built Lessonly to ultimately serve that need. It boils down to helping the organization drive both learning and then practice so that when those customer-facing teams are in action, they’re performing at their highest levels.

That’s the critical niche to the sales and customer service teams. Even when I was first exposed to it, I thought it was online learning or an LMS for everybody. That is like everybody else, isn’t it? 

That is exactly like everybody else. There’s probably 500 of those, maybe 600 now. When we started, there was 500. I’m sure there’s more. It’s a big market. There’s a lot of space for a lot of different folks. The way we saw it is early on we took a wide approach. What we learned quickly is if we’re going to drive value to the organization, it happens when a salesperson, a support person is getting better. Their CSAT scores are going up. We can show tangible ROI and value. The training burden is higher as you think about our business. Specifically, HR function in the business is running training maybe quarterly, biannually in terms of compliance, maybe some manager training. A sales or a support person needs training every day. We get a lot better usage and engagement with the tool and hopefully a bigger impact.

Is that the core of your model then, getting trained for fifteen minutes, half an hour training a day?

We focus micro in length when it comes to training. I’d be ambitious if I said teams are training every single day. Weekly at the least. Monthly basis, we’re seeing training happening in Lessonly. We’ve started to move also into more contextual training. We have a Chrome Extension essentially that follows the learner around the web. That says, “You might be in the middle of logging something in sales for Mr. and Mrs. Seller. Here’s a helpful lesson that might help you on this deal.” It’s not just to set aside training time, it’s also in the course of your day-to-day interactions interjecting ten-minute lessons into that.

Is that plugging AI into this one as well?

I wouldn’t call it AI yet but there’s some recommendations components. Simple stuff as well as a program owner saying, “I know in Salesforce when this is happening, this is a good lesson maybe to recommend.” It’s not quite the AI but recommendations.

Takes us back to the beginning how you and Max got together and how you decided to build this thing.

We were roommates. We’re based out of Indianapolis, Indiana which you don’t always hear. Some incredible companies have been growing here. ExactTarget being our best and brightest. In the early days, Max and I were living together. He had this inkling of something in the learning space needs to be done. I was his roommate at the time. I was working at a startup that got acquired by ExactTarget. Serendipitously, my job became training. I was a sales rep, but I was one of three people who understood the product we were selling. At the time, ExactTarget said, “You’re 24 years old. You’ve got no commitments. We’re going to send you around the world to essentially enable our thousand salespeople on this new product we just purchased.” One of our early beta customers was ExactTarget because I was in Australia for two months.


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I was in London and my only job was to train. We took the MVP of the product. I took it into my role there and said, “Instead of me doing all this travelling and sitting you in a conference room that nobody’s paying attention just trying to close deals, I’m going to send you a ten-minute lesson on this and then I’m going to go co-sell with you as we go along.” That was the point for me, “I love Max. We’re best friends. I was in his wedding. He was in my wedding.” That was the point for me at which I figured, “If there’s a problem for a big company like ExactTarget, there’s got to be one for others.” That was enough for us to join forces and try to make it happen.

You figured out the need for it and saw that you could do this thing together. How did you divide and conquer the roles?

It was honestly a bit of luck that it just so happens Max is a product mind. Not necessarily like a CTO type person, but focused on design, loves getting into the weeds of product. I was more focused on the revenue side. From the beginning, day one of the business it was like you go focus on the revenue side of the business. I’ll go focus on product, talent, culture and growing the team. That was it. It stayed that way since.

You are similar in a way in a setup to what Tobias and Harley did at Shopify. Tobias, the CEO, is inward product facing. Harley was outward facing, bus dev, sales and marketing.

The one unique twist for us is Max definitely serves as the face of Lessonly. He is inwardly focused on talent. He is inwardly focused on product. We launched as a company, Max wrote a book called Do Better Work. It’s the mission of the company. He’s out there on the road doing speaking events, some cool ones. Whether that’s with customers or events and promoting his book We were proud he got to an Amazon list bestseller. He’s the figurehead of the company. I tend to be inwardly focused in some ways and focused on customer interactions. That’s the one tweak that may be unique for us. We haven’t seen too many examples.

Walk us through your orchard. How does the company look, setup and scope? Then we’ll get into some of the weeds with you.

We’re going on about 150 folks, big go-to market teams. We’ve got a lot of those folks about 50 in the sales org. That includes STRs, AEs. We have a new enterprise segment. We’ve got a post-sales team that’s growing as that new business scene is growing. That’s about twenty. We got a 30-person product team and a ten-person marketing team. There are functional leaders across most of those. We have a revenue operations team that keeps everything intact. I’d say pretty typical, fairly growing services organization as well. An executive layer if you will of seven with each functional leader involved. BPSCX of HR, of products or revenue operations and of marketing.

Who reports to you and who reports to Max?

I take all the revenue side of the things, so CX, sales, partnerships. Max takes HR, product. We share revenue ops. I tend to work a lot with them. It’s a shared responsibility between us.

All of you employees, are they all in the Midwest? Are any of them remote? Any of them overseas?

We’ve got a few satellite offices. We started to grow a small team in Denver. Then we’ve got a few scattered folks. For the most part, we’ve grown the business in Indianapolis. Cameron, there’s a lot going on here. I think it’s an underappreciated city. We love it here. We found no shortage in talent. To be honest, it’s what a lot of people complain about. We’ve had a good time finding people here. In terms of the capital requirements to grow business, we’re just fortunate. The Indianapolis market is different. I can’t imagine what it’s like to grow a business out West or East from a capital perspective because it’s just night and day different. It’s priced 30% to 40% less expensive for us to grow people here.

The cost of talent?

Yes. That’s expands to office space and everything else, just operating capital. Less is needed which was great.

Do you think more companies aren’t trying? Are they making an excuse that you need to be in the Bay Area or VCs or around technology hub cities? 

It is a tight knit community. It would be hard for someone to just come in and necessarily plant roots here if they’re not from here. That might be part of it. The other part is what you’re saying is a bit of a belief to access the capital is tough, which is true. We’re not swimming in venture capital, although it’s growing. In my mind, it’s easier to go on a road show and raise some capital. We raised from an investor out of Boston called OpenView Ventures. It’s easier to go on a road show and do that for a couple of weeks than it is to plant there and grow more expensive business. That’s just one person’s perspective. We love it.

How much have you raised? What’s the future? Where are you taking the company?

We raised about $14 million. That’s through a series B, light on capital. That’s just a couple of rounds, three C and then an A and a B. We’re at the point where we’re in a cool position where we’re controlling our own destiny with some optionality. We’re in that phase where we’re getting to a point where we have a choice. Which route do we want to go here? We can run the business and continue growing it fast without additional capital. We’re also thinking about what would we do with that additional capital, go faster? Those decisions are behind closed doors being figured out, but it’s an exciting chapter. We’re fortunate to be in that spot where we’re not in a crunch to go figure either those options out. We’re trying to make sure we’re building solid business that has that optionality.

What’s the long-term plan? Are you going to try to take the company public? Will you continue to grow? Is it a strategic exit or continue to build an amazing company?

I think it’s the last one. I don’t think we’re close enough to seeing what an IPO would look like to be thinking about that. While we’ve made great traction, it’s not what we make up thinking about. Definitely, “Let’s build an excellent company.” Max and I have, as we reflect on every stage, it’s been so different at every stage that for us it’s a blast. We’ve got about 150 people. We can see the culture changing and forming. The momentum and the people getting fired up every day coming to work, that’s been our focus when that’s in the business. It’s not always there. It feels like, “This is challenging, but it’s fun.” As long as that keeps happening, we’re growing a great business. I figure the rest would take care of itself.

You mentioned that people come in and they’re fired up. I heard Herb Kelleher was asked ago, “How did you get all your employees to smile like that?” He said, “We don’t. We just hire smiley people.” I don’t think you get people fired up. You hire people that are fired up. Is that correct? 

Yes. One of the key things, especially on the sales org, we look for is our people fired up about something. An interview question is like, “What fires you outside of work?” You can always tell if somebody goes on a rant about this exciting thing to them. That’s a great sign. It’s one of those people that sees things with a glass half full. As you get more of those, the people that may not quite be that way almost have no choice but to fall in line with that. There are some things we do or try to do intentionally to encourage that type of mentality. One of them we made a core value, which highlight what’s working is the core value. The reason we did that was give this book to everyone. It’s a book on pursuit of inquiry.

I went to school at Butler, a huge Brad Stevens fan. He always recommends a book called Soar with Your Strengths. The idea of all of it is, “Let’s highlight what’s working so that we can do more of it.” Too often in these high growth businesses there are plenty of things not going well. When you choose to focus your attention just on those, you lose sight of the bigger picture. You also lose an opportunity to say, “The business is going well. Let’s do more of that.” The fact those stand is like, “Let’s go fix the things that are broken.” Sometimes you don’t have to be great at everything. Let’s be great at the things we’re good at and double down on those. That mentality has helped us keep that smile coming in the door or positive mindset. Putting it on the wall as a core value and living into that and modelling that has helped us encourage that environment.

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You mentioned the appreciative inquiry. Were either of you part of the CATCO organization in school? 

We weren’t. We signed them on as a client.

It’s funny because there’s a big movement with a bunch of guys that I know that have been in CATCO years ago. Hal Elrod, who’s my co-author with The Miracle Morning for Entrepreneurs and John Rowan, who’s coming from the Midwest. There’s a whole group of them that are part of this appreciative inquiry movement. Give us the helicopter tour of what the appreciative inquiry is?

At its core, it is about a tactic to philosophically dig into what’s working. The misconception maybe is like it’s this Tony Robins, always be positive type of thing. It takes a perspective and ask questions to see what’s going well. For example, Max and I might be talking about something. Max explains to me this troubling thing. It might be a simple question of framing in a more holistic view like, “How often has this happened? How impactful is this?” We get to the point where it’s like, “This is an isolated incident. There are all these other things going well. Let’s go fix it but let’s not lose sight of the bigger picture.” It’s the best way I can think about it. I’m sure that’s not doing justice to the entire book. It’s not an abstract to the book necessarily, but that’s the big idea.

I’m going to read it for sure. I was at an event related to Hal Elrod’s The Miracle Morning. He had probably about 150 of these raving fans from The Miracle Morning community. They were all doing this two-day appreciative inquiry, deep dive into what The Miracle Morning could be going forward. He kept getting all these ideas from the group and breaking the group off into subgroups. They decided amongst themselves how they were going to fuel this whole movement. Sitting back, I’m like, “The CEO is not even telling anybody what to do. His employees aren’t even the ones doing it. It’s his raving fans.” All the stuff that they’re excited about and where it can go. 

Can I ask what is The Miracle Morning? I’ve heard of that.

The Miracle Morning for Entrepreneur, Hal Elrod and I co-authored that together. He wrote the original TheMiracle Morning book around six morning success habits. He looked at all the most successful people on the planet and what they were doing and try to net it out. He came up with what he calls the six morning SAVERS. The first one is Silence. The first S is waking up and giving yourself a moment of silence in the morning to let the day come in. I sleep with my blinds open so that when I wake up, I see the natural light in the mountains and the ocean coming right into my room right away. The next one is Affirmations. A is giving yourself a morning statement that you will repeat to yourself until it starts feeling more true. Then you have your Visualization, which might be reading your vivid vision or part of your vivid vision or part of your plan for yourself, reading through that visualization. 

Then some morning Exercise. I suck at that. I like to do my exercise at the end of my workday and before I move into the rest of my personal day. There is some value to certainly getting the blood flowing. Even a seven-minute workout first thing in the morning or some burpees or something to get going. I finished my cold shower, I call that exercise. It sucks. The R is Reading, giving yourself five to fifteen minutes of morning reading. That can also include listening to an audio book as much as reading with your eyes. There’s a lot of value for people that struggle to read but are absorbing content from listening. The last is Scribing, which is writing. Just as journaling doing a five-minute journal or getting your thoughts out of your head. Those six morning SAVERS are the core of the Miracle Morning. 

I’m about 50% so I got some work to do.

I’m sure you got a bunch of your own as well. Walk us through the culture side. What else do you do to drive the fuel culture? I think the media has done us a disservice by pretending that culture is about the free massage and the free lunches. That’s not what culture is all about at all.

It’s funny how we’ve been fortunate online to get some decent reviews, whether that’s employees or people doing a research on Lessonly and they’re coming into an interview. One of the first things, “What got you interested in Lessonly?” It’s always like it’s the culture. The follow up question is, “What do you know about our culture?” Most of the time I read the reviews online and I saw the free LaCroix and the snacks just seems like a good vibe type of answer. That’s like a big red X for me. Unless they talked to someone, know people in the business. You can’t know it until you’re involved. I agree with you. It’s probably a number of things.

I’ll promote Max’s book. It’s called Do Better Work. We’ve got them everywhere, but we made these things because we get this question a lot. The one I’d share with you that has been helpful from my perspective that I’ve learned over the years is we promote a culture that leaders don’t need to know the answer. Which leads to a spirit of vulnerability that everybody talks about. It might be an interesting way to get to vulnerability. What we do well as an organization starting bottom up and top down is the humility. Maybe this is a Midwest thing, but we don’t have many egos. Oftentimes if a leader doesn’t know the answer, that’s okay. What that leads to as an organization from a culture perspective is if you think about we draw this Venn diagram.

There’s what the business needs and there’s another circle that is what gets done. If leaders are acting like they know every answer, oftentimes what’s getting done doesn’t overlap very much with what is needed in the organization. We try to get those golden circles to overlap. One of the greatest ways to do that is be vulnerable. When we don’t know answers, we don’t know where to go next. We don’t know what the next turn is. We ask a lot of questions. We get a lot of feedback. That leads to everyone in the organization doing the same thing. We end up in better spots. People feel a lot more autonomy in the path we’re going down because of that.

We were speaking about that in our COO Alliance Event. We were talking about how leaders should be the last one to speak at the table. When you ask a question, so often the CEO or the COO wants to chime in right away to give the answer. The answer is often in the room. Our job is to grow people, not to give them answer all the time. If we’re going to grow them, it means to let them give the answer. Often, they’re either going to be right or they’ll be better than ours or they’ll give them the confidence to speak. If we’re always the ones speaking first, it never comes out. How about on the interviewing side and the recruiting side? What are you doing? I know that you said that in Indianapolis it’s been great for you as a recruiting pool. You are starting to become one of the big names in that market too, aren’t you?

Yeah, that definitely helps. We’ve definitely hit a bit of an inflection point where at least nearby, and hopefully outside of nearby, people know who we are. That definitely doesn’t hurt.

Go back to when you were 20 to 50 employees or 50 to 100 employees. What were you doing at that point to attract people then?

Brute force referrals were one of the best ways to describe it. Taking risks on people with nontraditional backgrounds were the two strategies. For example, in the sales org, the first four salespeople I hired, none of them had SaaS or technology experience. Only two of them had any selling experience. We were hiring on potential and figured we could grow that. In the early days, that was the strategy, then bringing in referral networks from there. As we’ve grown, we’ve gotten a bit more scientific about this in terms of getting clear about what we’re looking for and what we’re not looking for in a role because we’ve hired more people than we can see.

One of the tools we use to do is called Predictive Index. We use that early on in our interview process. It predicts what environment is going to be driving for the person. For example, in a sales role, we look for what’s called low patience. Somebody who has a lot of high urgency, is ultimately a little bit lower on the formality side, but willing to not get it perfect, then high on the extra version side. They draw energy from people and interactions. That profile, we can stamp out early. It’s not a tarot card but it definitely helps. That’s one thing we’ve done as a tool as we’ve grown, as we’ve gotten more scientific about it.

You are starting to understand the core behavioral traits that make some of these roles tic. It’s interesting that a great salesperson will never make it through an HR screening process because HR people hate salespeople. People make it up on the fly, they’re winging it. They keep their energies too high. They don’t follow any of the systems. HR is all about, “No, we have a process. We have to follow it. We have to stay straight.” That doesn’t work in the sales process.

We’ve done that. That’s part A. Part B is throwing them in a real scenario. A sales that’s role playing a product, that’s engineering tests, things of that nature. We’ve gotten a lot more practical about speed to hire has become important. What we’re doing in 20 to 50 was a series of conversations over beers. Eventually, we’ll try to suss out a gut feel about you. It’s like, “We want to get to a decision,” both for us and for the candidate as well. Practically, here’s a job challenge that we want you to take on. It has been more illuminating than anything else, any question or any answer you could talk your way around.

You are also at a stage now where you’ve, at some point, had to have hired some mid to senior level people on top people that have been there for the original time. Some of them you’re going to hire above them. How did you do that?

We’ve done it a number of times. Our first head of marketing, he was the third person we hired. I begged him to come on to the team. I remember the sales pitch. He was at a big company making a ton of money. He was taking a 60% pay cut. My sales pitch was essentially, “When you’re 80, what are you going to remember?” That’s what got him to come on board amongst other things. He was with us from the beginning, Mitch Causey. Mitch always had ambitions to go off and do his own thing. Mitch spent five years with us. We worked together and he was incredible about it. He said, “I feel like it’s time.” We felt like it was time to think about VP of Marketing. The way Mitch approached it was, “If you get the right person and I trust you to get the right person, I’m going to learn so much. It’s going to build my career for the next thing I want to do which is start an agency.”

There was that side of it for him that he saw that worked with him. It doesn’t mean it wasn’t painful conversations. We got a guy named Kyle Lacy who has been incredible accelerant to the business. Because Mitch was so open to that, it was perfect. Mitch spent a year and a half, two years under his wing. Then we got to the point where Mitch was like, “I’m ready to start my own business.” He gave us six months’ notice. We had a big party when he left. That worked out incredibly. Mitch Causey, the guy in the seat before Kyle came in, is an incredible human being to have that humility and take that perspective. I don’t know how you do it if you don’t have that type of mentality of the person that you’re bringing over the top.

SIC 62 | Hiring The Right People

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You’ve touched on a couple of big things. One was that phrase that you used that I think is almost gold. It is the, “What are you going to remember when you’re 80 years old?” Do you want to just do that corporate gig? Do you want to do something special? Just shutting up the pregnant pause and let them sell themselves. You don’t have to sell the company at all at that point. The feeling of desire to want to do something better, which most people will never get a chance to do. The second one was when you have that senior person that wants to go off and do their own thing, you didn’t try to hold them back. It’s almost like raising a kid. Our job as parents is to raise the kids so that they leave the house and go to college and do their own thing. We can’t keep them under our house forever. 

This has been a driving factor and motivation for Max and I. It’s like, “People are going to work long part of their lives.” If we can give you a working chapter, whatever that chapter is, that is memorable, that you’re going to look back on and be like, “That was great, mission accomplished.” Whether that’s two years or whether that’s ten years, then our job has been accomplished. Hopefully, it leads you to the next thing that allows you to get a bit closer and explore what you want to be doing.

Then that celebration of that when he’s off doing his own thing and you help celebrate that with a party leaving. Did you take a percentage of his company when you helped him spread his wings?

We didn’t. We became his first client. He started a marketing design agency. I’m sure he gave us a favorable rate, I’m not sure. He’s too good not to hire. We ended up being his first client which we were glad to do.

I will bet that there’s a huge opportunity for cult-like companies like yours to help their employees go off or become their own entrepreneurs and take 10% equity positions in their company, become an early stage client, an early stage adviser and help them spread their wings. The reality is a lot, especially Gen Y, when I grew up running your own company was evil. You were eccentric, greedy, a capitalist. Even my aunts and uncles thought that I was this weird kid for wanting to. Nowadays, running a business is cool. Running a business, being an entrepreneur is a cool thing. There might be an opportunity there for companies to help Gen Y start their own and become an entrepreneurial incubator of their own people. Walk us through some of the operational stuff. You have had an easy run in terms of the five. I’d say that it’s been an easy ride from zero to 150, but clearly it hasn’t been.

No, not at all.

What are a couple of the big struggles, the lessons from the edge? Did you ever almost lose the company?

No. Fortunately, we have not been in that boat.

How about a big holy crap moment? Losing sleep for a couple of months? What were the big things? What did you screw up or the big lessons?

We’ve been fortunate to not have any catastrophic ones. I’ll share some of the ones that I remember at the time felt like the world was falling down. I remember there’s one where we used to run every trial business as a strategic initiative. We were always trying to get this free trial conversion rate up. One of our strategies was to hire someone who was maybe over experienced for an inbound STR role but helped us figure this out. We hired someone. They’re often running it. We figured that had the right experience to do this. We wake up one day and we realized I don’t remember the exact time frame. We were talking about what was digging into some sales reports or something and realized for six months we hadn’t followed-up with our highest score leads. No calls, no emails. Max and I were fired up. It was one of those moments where we had been talking to the board about improving this trial conversion rate. Here’s our strategy. We go to do it and we had missed that. We weren’t calling literally the best leads in the pot. In the grand scheme, it’s not bad, but in that moment, it felt like we are going nowhere. “What are we doing?”

How did you uncover that?

It was our Director of Marketing. He was digging into the reporting. He looked at a lead record that was a good lead from a big brand you would recognize like, “We haven’t called this one yet.” Then he looked at the next one and he was like, “We haven’t called that one yet.” Somehow over the six months we didn’t see, the conversion rate was flat. The high level metric, it didn’t drastically go down or up which was weird. Maybe there was a lag time in that because it takes some time to close the deal. We were looking at the wrong things. Somebody ended up drilling down the levels deeper than they needed to and realized it.

We’ve got Scott Dorsey and Mike Fitzgerald from ExactTarget on our board. They’re great mentors in the business. One of the things Scott Dorsey is incredibly good at, every time they call him with something like this which I’ve picked up just by his modelling, is in the moment of something like that happening, he’s so good at pushing emotion aside like, “What’s happened has happened. What are our next best alternatives from here?” Eventually, he’ll come back and address the situation, but for things in the moment that are critical, we got to act quickly. He’s so good at staying calm and saying, “Let’s talk about the next alternatives from here. In a week or two, let’s come back and address what the problem was.” In the moment, I’ve never seen anyone as good as him at helping us through those things.

Scott Dorsey has done an amazing job both with ExactTarget and the portfolio companies he’s helping to steer or involved in. Does he get actively involved in the business as a board member?

He does. He’s not on that many boards to be honest with you. We feel lucky. He’s on a publicly traded board at Pluralsight, which is a great, cool experience that he has there. Then a few others outside of Lessonly. When Scott commits to something, he commits to it. He’s the type of board member who’s not hovering over us and asking us a ton of questions day-to-day.

I think back to when you were talking about the whole you weren’t even phoning your top sales leads and how that it was almost like how could we have not been. I heard a saying years ago, “Inspect what you expect.” As a leadership team, “We’d be calling our top leads. Maybe we should look at that. We treat our customers. Maybe we should look at that.” That’s something I need to even do more with the COO Alliance and the company I’m building. Even one of the CEOs that I’m coaching is to get them to dive in and look. It’s amazing how often stuff isn’t getting done. 

It’s a muscle I’ve had to build personally because I tend to be the less detail-oriented type. It has been a hard lesson to learn over time. The other one I would say is another core value we have here because of things like this is that it’s so important to get agreements amongst people. That’s different than expectations. In this case for example, my expectation was you’re calling the best leads, but I never said that. I never had that agreement of, “Let’s pound fists. We’re walking out of here doing this.” We’ve gotten a lot better across the organization and try to model this from Max and I. It’s like, “Let’s not keep assuming things and expecting things of each other. Let’s get agreements. Let’s negotiate the agreement.” It doesn’t have to be like, “Conner told me to do this so I’m going to go do it.” It’s like, “Can we get an agreement on this and let’s negotiate what the agreement is.” Then we’re both bought into it. We both end up in a much better spot.

I like that whole agreement component to it. The military used to have a mantra of, “Plan, brief, execute, debrief.” The agreement part would probably come in on the plan and briefing component. Then we go execute. Later, you can circle back and debrief on it. You touched on something else. You said there were two things. Core values was one. What was the second part that you mentioned? What are your core values? How many have you got? 

Highlight what’s working, get agreements, ask clear questions is one. That’s all about in the spirit of not assuming things but asking clarifying questions in the spirit of, “Let’s get to the root of this.” That can be as simple as, “We’re having a meeting. What’s the goal of this meeting?” all the way down to continuing to ask why in certain scenarios. That’s been helpful. We put learners first. It’s an important one. From our business, a lot of people in our space, you lose sight. At the end of the day, our goal is to make someone better at their job. That’s one. Make time for life is another. As demanding as this can be, mental health outside of the job we realize is the core of life. This isn’t the end-all be-all.

This is what we do to make money. If we can’t have some fun along the way, none of these matters in the first place.

You’re in the mountains looking outside, waking up to the sunrise. I think you’ve got that figured out.

You said it was a muscle that you were trying to build. As a leader, we always have to try to grow ourselves. Our job as leaders is to grow people but we also have to grow ourselves. If we think at Lessonly, one of your core values of putting learners first, how do you focus on your own growth as a COO? What have you focused on growing your skillset over the years?

There’s a few that come to mind. One of them for me has been, and this is the last core value I left out, we have difficult conversations. It’s part of my going back to PI, the high extra version which is me tends to drive. I’ve had to work out the kinks of myself drawing satisfaction, energy from the acceptance of someone else. Difficult conversations have always been tough for me because it’s like, “I’d rather just work around this and not address it directly. I don’t want the person to feel bad.” That type of mentality has been something. My development tactics, a lot of them have been in partnership with Max. We have the type of relationship where we can tell each other things from our perspective of, “This area you need to focus on.” That’s the one he’s challenged me on and I’ve tried to get better at.

It’s hard for a lot of CEOs to find the second in command that they have that implicit trust. You were lucky that you had that relationship before you started working together.

I don’t know what I’d do. My view on second in command stuff, that CEO job is so tough for so many reasons. I got some advice from some of the folks at OpenView. At the end of the day if you sit in a seat like mine or like yours, a lot of ways you got to dive your own ego. You got to ask yourself, “How am I useful to the CEO, to this business?” Let the rest take care of itself. That type of mentality is one where at the end of the day, the people in the business who know the business are going to recognize the impact you’re having.

My mindset coming in every day is like, “How can I help him make that job a little bit easier? What can I be thinking about day-to-day that takes some of those concerns and worries off of Max’s plate in this case?” Over time you build the respect of each other. What Max and I got into, the driving motivation I think for both of us we talk a lot about is we have two very different focus in the business. He’s product, I’m revenue. We have a bad revenue quarter, I don’t want to let you down. If we have a great revenue quarter, he’s like, “I don’t want to let you down on the product side.” We need to be serving each other as best we can. That together ultimately makes us both sharper and better. Without that, it wouldn’t be as fun, number one. Number two, I think it would be hard day-to-day if we didn’t have that level of trust.

We were talking about this at the COO Alliance event. The COO’s job is to make the CEO iconic. The CEO’s job is to play behind the scenes to almost support us so the team realizes we’re not jerks. We have to be the ones making all the tough decisions. How do you support each other? Can you give us a specific example of how you might support each other, how you make it iconic and how he supports you as being the operations guy in the business with the rest of the team?

Part of it is focused in attention. A personal passion of Max, or a lifelong goal, was to write a book. I’ve talked about the book already. That took six months. He’s writing this four hours a day. He put a lot of time into this. A tactical example of that was me having trust that, “Six months from now, this book is going to come out. It’s going to be great for the business. It’s going to be great for you personally.” You can imagine in those moments, and Max won’t mind me sharing this, he’s sitting there talking to me about, “I’m almost feeling guilty for doing that.” The book came out six months later and he’s on fire about it because it worked. It was trust that that would work. That’s me trying to do the things behind, which is run the business, keep all the revenue thing, all the stuff that keeps the business running. He doesn’t have to worry about it. He’s writing a book. It’s how to make that the iconic side.

What Max has a gift for when it comes to reciprocating that back to me in this case is just appreciation. That’s all I need. Whether that’s a text that says, “I recognize you did a great job here.” That’s what Max will do is occasionally write a note to our board and recognize something I’ve been doing. That’s all I need. Make sure you don’t lose sight of the tough work we’re doing here. I save those things because he’s great at giving specific compliments that make you feel in those moments where you’re like, “Can I do this job well?” You go back to those things and it helps you keep known that the person you’re working with day-to-day, your partner has trust in you. That’s how he reciprocates it.

SIC 62 | Hiring The Right People

Hiring The Right People: What you’re doing may seem insignificant, but the important thing is that you do it.


You have done the Predictive Index profile with each other. Did you do your love languages as well? Is one of your love languages words of affirmation?

It is. I think we both did it. We’re both the same in that.

We’ve started doing personality profiles not just with our COOs in the COO Alliance but also the CEOs and then with their teams. The love language is a bizarre one. When you do it for your team members and you understand their love languages, you understand how to either praise them, give them a hug, give them a little gift. The next one is they also came up with one reason. They call it the apology language. How do people like to be apologized to? How do they like to be either shown or told that someone feels bad about something? That’s an interesting one inside the company too. Lessonly clearly is one of these top, big emerging software companies. What do you as a company see as some of the top software platforms out there that the entrepreneurial mid-sized company should be using? What software tools do you use that are accelerating the business from recruiting, interviewing, selection, onboarding, culture training, operations?

On the sales side, I’m a bit biased here, there’s a tool called Doodly. It’s a tool for salespeople. It started as a way for salespeople to take notes and get them in Salesforce which sounds simple but is amazing. It’s evolved to updating everything you need to in Salesforce in a simpler, easier to use interface so that our sales reps don’t spend day-to-day in Salesforce and are getting accurate forecasts and stuff like that. That’s on the sales side. On the product side, there’s a company here in Indianapolis called Woven. What they do is an engineering type, recruiting platform that I’m not well-versed in. I know the team has been super pumped about the speed at which it helps them hire and get through engineering tests. As well on the product side, our product leader loves a tool called Officevibe. It’s a polls-type tool for employee sentiment. It does it in an interesting way. Those would be three that come to mind.

Are you Salesforce partner? 

Yup, we are. Salesforce launched a competing offering. It’s been years in the making like most of their new products. That’s not a dig. They did launch a competing offering called Trailhead, but we’re still a Salesforce partner because sales and service reps spend a lot of their day in Salesforce.

What’s a good sales contact manager that works that you don’t spend hundreds of thousands of dollars trying to get work? 

For the first four years of the business, we use one called Pipedrive that I think a lot of people know. We had this ceremony, fake funeral the day we had the CD rom. We put it in a coffin and buried it. It’s the day we had to get rid of Pipedrive because it was a sad day for us.

Why did you have to get rid of it?

Mainly reporting, honestly. If they could have given us more reporting, Salesforce, as we’ve grown in sales operations and gotten sophisticated with stuff, wasn’t cutting it.

Final question, if you’re to go back to your 21-year-old self because we would never listen to our parents or anybody else when we’re 21, but if you could listen to yourself back then, what word of advice would you give yourself now that you now know to be true as a leader? What would you have wished you’d known earlier?

One of the lessons I’ve learned, I’m a big fly fisherman. It’s coined in the fly fishing world, but it’s called river hours. River hours is this idea that I’m going to walk out on to a stream. I’m going to spend eight hours fishing. I may not catch a single fish, but if you take a mindset of those eight hours were river hours I spent to get one step closer to a fish, it’s a mind blowing shift for me. It’s a lesson in, “What you’re doing may seem insignificant, but the important thing is that you do it.” You realize you’re getting one step closer to whatever it is you’re reaching for is the lesson in that.

That has been, over the years, something I’ve learned that has quelled some of the lack of patience I have. The frustration is if it’s not coming quickly. That’s been a lesson over seven years of building a business. I’m always thinking like, “Why can’t this go faster? Why can’t this be better?” I’m always comparing myself to the high flying, huge fund raises, billion-dollar companies. Sometimes it’s about the river hours and the time you’re putting in. You’re ultimately getting closer and you might not even realize it.

Conner Burt, President of Lessonly. Thanks for sharing with us on the Second in Command podcast. I appreciate it.

Thanks, Cameron.

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