E51: How Lightspeed Commerce Built a $1B+ Sales Engine - JD Saint-Martin, President @ Lightspeed Commerce

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

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Today's guest is JD Saint-Martin, who is the president of Lightspeed Commerce, which is a cloud-based online and offline commerce platform, uh, which serves 326,000+ SMBs globally. And JD joined Lightspeed in 2019 through the acquisition of Chronogolf, which he co-founded with Guillaume, who introduced us. So shout out to Guillaume. Everybody take a look at Vasco for all of your AI RevOps platform needs. And that was a SaaS golf course management platform. That you guys co-founded in 2013. And then JD rapidly advanced through the leadership ranks at Lightspeed, going from, you know, a lowly senior director when you joined the company to now president running a bunch of different functions within a 3-year time horizon, which is certainly something that we're going to pick apart today. Prior to your entrepreneurship times, 5 years in venture capital at Terralyst Capital, GE Equity, clean tech, SaaS, a bunch of different stuff. So I'm excited for this one and thanks for joining.

Yeah, thanks for having me, Kyle. Super, super nice to do this with you. And as I was saying earlier, I listen to you regularly and religiously in my car. I have a long commute, so it's nice to actually put it in real action and see your face through the computer that way. It's really cool.

Yeah, yeah, this will be fun. Now you can listen to yourself on one of your drives. Yeah.

I'll try not to do that. I really cringe when I listen to my own voice, so, you know, I don't know if I'll listen to it.

Yeah.

But yeah, I'll listen to the others for sure.

It probably makes me a bad podcaster because I never listen back. I'm like, I can't do it. It's just too, too cringe for me to listen to my voice for, for an hour and a half to, but I, maybe I should to get better at it, but, uh, you know. That's how it is. So what did I miss in your background? Fill in the blanks for folks with sort of 60 seconds on, on the career journey. Oof.

Uh, no, I think, I think you nailed it. I mean, yeah, maybe a tiny thing is I, I'm, uh, I'm, you know, as, as your listeners will pick up from my funky accents, I'm French Canadian. So I apologize if I make some mistakes here and there, but I was originally born in Ottawa from, uh, from Canadian diplomats. So I, I've really like had privilege of living all over the place, all over the world when I was younger. That's really shaped who I am today. And as you said, I started my career in VC, private equity, then crossed over to, I guess, the side of the light or the dark, depending on which vantage point you take, as a founder and entrepreneur. And then now as an operator, my company got acquired by Lightspeed. So the last, last 6 and a half years has been drinking from a fire hose, I think is the best way to frame it. Like I joined Lightspeed, we're doing $75 million in revenue. We're on our way to $1.2 billion in recurring revenue now.

Wow.

Yeah. So it's been a, it's been a pretty crazy journey to say the least. Uh, and, uh, yeah. And it's just amazing ride, learned so much.

Uh, so, so yeah, I had no idea it was only $75 million when you joined. I figured it was way bigger.

Yeah. Lightspeed went public on the TSX in March 2019 and the fiscal year end we, we, we had just closed was, um, was, was, was that number. And then we grew organically and inorganically. So we acquired, in my, in my time, we acquired 10 companies, different sizes, but we also grew massively, Kyle, because we are, as, as you know, we're a vertical SaaS player that added payments and now also capital. So we have like a full financial service offering on top of regular subscription revenue. So obviously that accelerated a lot, the revenue arc that you see there as well. It's been, it's been, it's been growing like gangbusters, frankly, for a while and now growing efficiently. It's one thing to grow, but you gotta, you have to do it efficiently and profitably. So yeah.

Yeah. Well, we'll, we'll loop back to efficient, efficient growth and infrastructure and all that good stuff. I want to ask a little bit about the journey because it, you know, that's a rarity going from. Startup founder, get acquired, and then 2 years later, your CRO, and then very shortly, the president. What did you have to change about your approach going from startup guy to public company executive? And maybe what was the same?

Yeah, I mean, so to be honest, this was not planned at all. I would say when we, when we were acquired and we can revisit like why and why did we decide to choose that path? You know, because we could have continued Guillaume and I to grow the golf business and it's been, it's been a, it's done phenomenally well since the acquisition. But when we decided to partner with Lightspeed early on, there's a gentleman who I have to give a shout out to because he's someone who, who believed in me and gave me that shot, our previous CEO and president, JP Chauvet. When we're discussing the acquisition and kind of like the post-acquisition playbook, it was pretty clear that there was a need internally in the organization to lead account management and customer success, which is pretty uncommon to do when you acquire a company prior to even like signing the docs. Like we were already forming on, yeah, like what, what the world's post-acquisition will look like. And my skillset. At least from his perspective, it was all kudos to him. I didn't see necessarily that in myself, but he saw an opportunity for me to take on that role early. And I think another per— another person or a friend we have in common is, uh, Julian Teixeira, who, um, moved on to, uh, to become the CRO of 1Password. So, so that also kind of snowballed when, when Julian left, uh, to join 1Password, you know, that's when, as you called out, I was a, I was a senior director, um, JP kind of saw what I was able to do in a short period of time with AM and essentially gave me the reins of global sales. And then that kind of cascaded and cascaded. Um, and it's just, yeah, I think circumstances and just someone at the top having that belief in me and me just kind of like running with it and working as hard as I could so that I wouldn't disappoint him, frankly. Because everyone else, I think, thought like, what the hell? Like, this is a weird, this is a weird decision. But I think going back to the founder thing, I think what's maybe particular in my case and arguably what all other founders normally go through is that beyond, yeah, like as a founder, your title says like CEO or whatnot, but really what you're doing, like we're a much smaller organization at the time. What I was doing was every single role in go-to-market, right? Like I was a marketer, I was the SDR, I was the AE, I was the implementation consultant, the AM, the support agents, doing support at night, on the weekend, working 6 days a week. So it's like doing all of these jobs for 6 years in a life-threatening intensity. So I think when I joined Lightspeed, that was definitely my, my unique skill sets is that I had like built, whether if I liked it or not, like such empathy for each of these roles and what it takes. And so I think that, that in itself gave me, gave me an edge and what allowed me probably to grow in the organization. And the other is golf courses have a, so Lightspeed, we sell software and payments and capital solutions to retailers, restaurateurs, and golf course operators. And so starting from golf, you know, for those of you that listen and play golf, you know, there's a pro shop in a golf course and then there's a restaurant. And so I basically sold to the Lightspeed ICP, myself for 6 years. So yes, this is the golf, but it was, we would actually bundle Lightspeed in our, in our offering. So when we were acquired, we're the largest reseller of Lightspeed technology, even if we were—

oh, I see. Okay.

So I came in, it's like I knew retail inside out, I knew hospitality inside out, I knew the products inside out. I demoed the products and then I did all of the GTM roles on steroids. So I think that was kind of like my, my edge. Um, and, but, you know, but beyond that, I think it's ultimately, it's someone believing in you and just kind of, you know, and taking that opportunity.

And so what did you have to change going from being a founder, doing all this stuff to operating as a public company executive?

I think mainly, you know, obviously to give you a sense of scale, when I joined the company that we ran, Guillaume and I, when we were acquired, we were about 60. Individuals across all of our functions. Today, Lightspeed, and it's like, this used to be a claim to fame, it's not anymore, to have a lot of people in your organization, obviously, but just to give a sense, you know, maybe not a good representation beyond the revenue, we're about 3,500 at Lightspeed. In my organization specifically, as president, I lead all of go-to-market, we're 2,000 folks, including 700 quota-carrying reps. So for sure, I mean, You know, what had to change for me is that I was accustomed, and I'm a control freak, Kyle, so I was accustomed to doing everything and, uh, and then going, you know, behind everyone and just making sure everything is done the way I want to see it. I think the biggest change has been to like, you know, to let go in some ways and, uh, and, and trust, uh, and trust the rest of the team and trust the, trust the group that we're assembling. Um, Well, I have a great, uh, we have a great leader here, um, very seasoned leader called Mike Gensu, who leads our retail operation here in North America. And he likes to say like a blue collar, uh, leader, you know, a leader that rolls in the mud. Like I, while always keeping that, that, that, um, approach, but yeah, I've had to, I've had to find ways to, to dedupe myself or to find ways to not be the bottleneck because that was my, my go-to was just taking on too much. So it probably in the early years, I, I took on way too much and now I think I found the right system and the right rhythm and the right team so that I can leverage the rest of the group and we can work as a team in symbiosis.

Cool. What do you mean you have to always roll in the mud? That's a great saying.

I think in order to solve problems, you know, there's different types of leadership. Don't get me wrong. I'm not saying this is the way to do it. But I've always admired the leaders that are able to walk a mile in the shoes of the people that they're leading. And so, and so whether if it's the people or the problems you're trying to solve, you, you have to, you have to actually do the work. Like you have to actually live it. You have to get into it. You have to get into the details, certainly at Lightspeed, maybe more so than other organizations that are a bit more well-oiled and have grown. A little bit more linearly. It's a, you know, every time we hire here, particularly leaders, I always say like, you know, how comfortable are you with chaos? And, you know, is chaos energizing you or it's like, it's taking energy, sucking energy out of you. It's a very chaotic world, you know, in our world because we're growing quickly. And so the way to get to see through the noise, like you have to roll in the mud. When I was younger, I played rugby in university and in Italy. Uh, and I didn't speak Italian and didn't know the rules of rugby. So I can relate back to that. Like the way I got, you know, I guess I got accepted by my peers was by rolling in the mud and just doing the work and being, you know, being there in the trenches with everyone else. Uh, and I think the best leaders going all over the place, but, um, I think that's, that's, that's an important characteristic that as a founder, you kind of, kind of inherit and build that. By default.

Yeah, makes sense. If you went back to your early corporate days, what's the one piece of advice you would give yourself?

When you say early corporate days, as in like at Lightspeed specifically, or like—

Yeah, yeah, yeah. Going from founder to like now being a corporate exec.

Yeah, I mean, so there's multiple sides, I guess, to that question, because it really depends what role What role you do, but let's say I would say day one post-acquisition, you can go back and be like, JD, I've, I'm from the future.

I want to tell you one thing as you're like on your first day at this new company Lightspeed. What advice would that be?

Yeah, I would say, well, again, like it depends, it depends what your, what your role is in the, in the organization. But let's say if I'm a revenue leader or a go-to-market leader at Lightspeed or joining Lightspeed in the context of, of go-to-market. I think the advice I would give myself or give this person is just the importance. And I mean, this, this is front and center nowadays and what people talk about, but the importance of, of, of spending the time to understand the operationalization side of the decisions that you make. You know, in theory, go-to-market leaders are, at least the good ones are good at playing like the full orchestra, not just this instruments. Um, and so understanding what's behind the scenes. So like an example of that is like, okay, we want to grow, you know, from, uh, you know, X to Y in MR, or we're going to, you know, we're going to go from 20 to 50% year over year growth in this motion or in this area, in this region. It's, um, it's very easy to just approach this with like, I'll just add a bunch of reps and, you know, everything will kind of work out magically. And it's like on a spreadsheet, warrior type of planning, it's a lot, it's a lot more complicated behind the scenes. And so really investing the time and the energy to actually understand the systemization side of those decisions and what needs to happen from an operations perspective for these things to come through. I think when you're a founder, because I'm relating it back to your first question, you can see everything. It's just, you know, like it's a small group. You can kind of touch everything. So you don't lose sight of what really happens behind the scene. As you grow, that's the biggest challenge. You kind of gain altitude, you lose sight of some of these decisions and what it actually takes for that plan to pan out. And so I think, yeah, I would say like that's something that I would give myself as an advice that I mean, I learned along the way that like, you know, you know, making these plans like, okay, you know what, like this was a lot trickier than we thought and here's why.

Yeah.

And, uh, and I know, I mean, having listened to you over, you know, uh, over the years, you've mentioned a lot like the, the importance of investing in revenue operations and, and all that, but it's like everything, all the cogs in the system, right? Like the infrastructure, the enablement ops data, you know, systems investing a lot of energy there and understanding how that works. It will, uh, it will save you. From making very costly mistakes.

Yeah, couldn't agree more. So I want to transition to the, our first sort of major topic, which is how to build a high-performance culture and what are the building blocks of building a high-performance organization. And so maybe let's just outline some of the foundation pieces first. Like, what do you think those, those blocks are? And then we can dig into each one.

And yeah, yeah, I was excited to unpack that because I think we've tried different things at Lightspeed and it's hopefully going to help, uh, folks out there too. So yeah, I mean, the different blocks, I mean, look, I mean, obviously it starts with like the people you hire, whether if it's like from an IC or, you know, leadership perspective. And for us at Lightspeed, I kind of touched on the leader side, but on the IC too, we're like, we're a little quirky, I think, Lightspeed, like we're particular, we're unique. Uh, I, I know everyone says that, but I, I, I truly believe that's true with Lightspeed. Um, and, um, and I, I, I, I think it's very clear over the years that we've had a lot of success because we've, or at least from my point of view, my vantage point, we've had a lot of success because we've been pretty candid with everyone that like we're not for everyone and the people that join us like need to, you need to be. In that mindset. So I think like the best advice I can, I can give to someone out there as they're thinking about like building a high performance culture and starting at the bottom with hiring ICs, it's like you spend a lot of time understanding like what you're about, what your culture is, what do you stand for, and be as prescriptive as you can when you are hiring by laying all the cards on the table. It'll save you a lot of grief down the road. Now tactically what that means for us obviously is that we go down to when we hire particularly quota-carrying reps, you know, we'll go down to say like, look, like this is a tough job and you need to understand that going into it. This is the number of calls, you know, let's say if you're an outbound BDR, like this is the number of calls we're expecting you to do on a daily basis. We have a pretty high cliff, so you know, 60 to 80%, like if you just get to 60% of your quota, you're not making your variable, like just being, you know, being very clear upfront. No, you know, we'll invest in you and we'll invest in the training and all that, but being very clear upfront that this isn't for everyone, I think ultimately leads to people kind of like going in there with eyes wide open. And then same goes with the leadership side. We've had a lot of, you know, we've had leaders over the years that came from incredible backgrounds and incredible CVs, but because of how chaotic our environment can be, it was a bit of a shock or a bit of a surprise. So I'm always like very, I try, I've learned to be more and more candid over the years. I, after all, have diplomat parents, so I, yeah, keeping beautiful pictures. Now I'm a lot more direct, but it's like, yeah, like same with your leaders. Like, hey, here's the situation. Like, this is what you're walking into. You know, obviously nothing is incredible and great and beautiful. Like, there are things that are going well, but there are also a lot of things that are broken, and this is why you're coming in. You know, I'm being very upfront. So I think that it starts, sorry, long-winded answer to say it starts there. Like if you're going to drive a high performance culture, it starts there.

Starts with hiring. Yeah.

Uh, and start with being, starts with being very clear what the expectation is upfront, not, not after the person started, because then you will, you will pay a terrible price if that's your approach.

Yeah. We're the same way and we even have this, uh, process where we We'll record a video that we send to the candidate ahead of the first hiring manager screen. So after they've met a recruiter and they're going to meet, say it's my role, I'm hiring for a senior role. I have like a 30, call it like 22-ish minute video that people can watch about like what problem zone are solving and how are we structured and where are we going and the role. And then at the end, it's like, What do you need to know about Honor's culture? Very intense, very high expectations, high pace, not a work-life balance culture. And I go through like what's good and what's not good. So people know that going into the first conversation. I've had good candidates pull out after watching video too. They're like, hey, and it's always extremely positive. Like, I'm actually really grateful that you sent this video. And, you know, like, I understand what you're building, but like, I'm not at a you know, I'm not in a position in life right now to like make that type of commitment or, or whatever it might be. And, and they're like, you know, we can pull the, we can pull our meeting. And like, you know, I, I really appreciate the transparency. Everybody is very appreciative of the transparency.

Yeah. I imagine all the time you saved on both sides, right? Like bringing on a person who honestly wasn't really about that life, so to speak. And then you onboard them, you enable them. I mean, yeah.

That's, uh, yeah.

Yeah. So for sure, for sure that I would, I would start, I would start there. I mean, we can get into our philosophy around like comp plans and how we, how we structure them and so on, if you'd like, but yeah, we're going to get there for sure. What, what, what we were also very maniacally obsessed about here is, you know, there's this saying, I think it was like, uh, Drucker, a gentleman, uh, kind of like the godfather of management consulting that said like, you cannot manage what you don't measure. For us, we're very obsessed with measuring activity, quality, outcome metrics, showing it to everyone, showing it to all leadership meetings, putting these leaderboards everywhere. Back in the day, um, so our office is in Montreal, hence my funky accent, as I said earlier. When we got this office, we were originally on the 4th floor. And the fourth floor, the entire GTM team at the time was, was on it and was set up as a, as our customer journey. So you'd walk out of the elevator and then you could kind of follow the journey and then leaderboards were everywhere and you know, you, everyone could see where they stand. And not just on, you know, where you stand on AR, MR and relative to your quota, but you know, how many calls you placed today. So it's like, it's a very transparent. Culture as far as like how we track metrics. And so I think that's, that's, that's critical. Like if you're going to drive performance, that's, that's, that's a critical piece. We've also invested— yeah, go for it.

It just— I want to ask a question about the metrics. So how much, how much weight do you put on input versus output metrics? Because, you know, like managing to the dial number oftentimes just means people making ghost dials and, and, you know, it's vanity metrics versus if it's too much focus on an output metric, then they might not do the inputs to get them there. So how do you think about what metrics to put at the forefront? What do you focus the rep on, the manager on? Like, how do you think about it?

So, so they're all important, uh, in my opinion, because then the challenge is you don't know what to fix or what to improve or what to work on if you don't give attention to, to all of those things. So like in theory, to your point, like typically we bucket them into 3. So you have your activity metrics, you have your, what I call kind of like your success metrics and then your outcome metrics. So let's use again a role like a BDR or an SDR. So number of dials will be the activity metric, like the prime activity metric we'll track. The success metric will be qualification rates. And then the outcome metric will be SQL or MRR, like when you learn or the AE that closes. We have ranges of what we expect in each of these 3 buckets for each of the role. We have 3, basically 3 leading metrics for each of these 3 pillars defined for each of our roles. At Lightspeed, we do inbound, outbound partnerships, and inbound we do field as well as remote outbound. So we can get into that because they're all quite unique roles. But we, yeah, we track all that because if you don't track that and you don't make it very clear that in order to be successful in this role, this is where you need to be from a range perspective in these 3 areas. Well, then when things are off track, you don't know what to fix. You don't know what to correct. And so then going back to your question on the manager front, our managers are expected to manage their individuals and their teams. Like if you're, you know, kind of like a frontline manager based on that, like we, I kind of like use the, if you know the Maslow pyramid of needs, yeah, I kind of use it in the context of a manager. Like as a manager, you need to Always think about coverage. Like that's the bottom line. Like you need to hire and need to be overcovered as you move up your, the chain of that pyramid. The pyramid, the second dimension is activity. Like that's just 100% under your team's control. Like if your team isn't producing, let's say dials to use the metric still, the number of dials that is expected as an individual and as a team, that's, that's 1000% on you. Like they will fire you.

Unacceptable.

Unacceptable, like a minimum condition for employment kind of thing. Then like, and that's, then as you move your way up, then it's like you go from activity to skill. So then it's like, you know, like the mastery in the role, the dexterity, the, you know, like the ability to convert those dials into demos or convert those demos into signed customers and deal sizes and so on. And then as a manager, then the last, at the peak of the pyramid and the, and kind of that framework is the engagement and kind of how your team is impacting the rest of the, the, the org and the culture and the career growth of your team and, and, and all of that. Right. So, so it's like if you're not tracking, going back to your question, if you're not tracking those numbers, all these buckets, it's, it's very hard to figure out where to focus and, and, and what to change.

Yeah. The other thing that we spend a lot of time on, and it's been in the last sort of 18 months, is baking in our company values into that same pyramid and it's like, it's in our promotion framework now. It's in how we recognize folks, but like, are you living the company values? Because the company values aren't just like, you know, like things on a wall, which oftentimes can be the case. Like there are things that we do deeply believe in and Adam and I from day one saw the world in like a cohesive way, you know, this obsession with learning and growth. The, uh, this ownership mentality. There's a bunch in there that we actually want you to be demonstrating and living day to day to, to, to be eligible for a promotion. And so now we've got this like 3-door promo framework where it's like your, your, uh, metrics are door 1. You can't get to door 2 unless you can have like great metrics. You don't have to be the— it's not only the very first top person. but you gotta be in the top like 10%. And then the second one is the skills. Do you actually have the skills to execute and potentially do the next thing? And then the last thing is the values. Like, are you living those values? Do you think you have built the right foundations as a corporate athlete to be able to do something that's harder and more intense? And so I think our language is different, but this, I very much align with this hierarchy.

Yeah. And maybe you give me some thoughts to build on what you just said there. So at Lightspeed, what we do too is So first of all, like we, we even in our IC commission plans, typically, I mean, there's some exceptions here or there, but typically it's 80% on the individual outcome KPI, like let's say MRR, AR that they're focused on, 20% on the team. So we have a team component to encourage, yes, and then we'll get into how people get promoted and all that. Particularly as ICs, but, you know, as I liked what you said, where you said like, you know, it starts with the metrics. So you got to hit your individual metrics, but we also put our money where our mouth is in order for you to hit your full variable and your full comp. You also want your team to hit. And so we incentivize the individual, you know, when they're at target, like they're going to help their colleague get to target as well. And then we have 6 guiding principles at Lightspeed. And we have a Changemaker Award. Program. So every town hall and its team submitted by region, by group, then it cascades all the way up, like for like the kind of the best of the best in the context of these Changemaker Awards. And it'll be like financial, you know, reward, but also company recognition. And this, this is peer voted. And so beyond individual achievements and team achievements, you know, are you, uh, are you living the guiding principles kind that we all believe in and are you demonstrating examples of that? And then we, we celebrate it, we showcase it, we encourage it, we highlight it to everyone. So cool. It's kind of systemizing that. I mean, again, like as you, as companies grow, you kind of have to systemize this thing in order to keep, you know, so that it continues to live. So yeah, we, but I, I really like what you said there. I think it's, it's so, so critical.

Yeah. And the 6 guiding principles, are those the same as the company values or is that guiding principle specific to GTM?

No, it's company values. Yeah, because you want to break the silos. Like we don't want to necessarily create like GTM guiding principles that are different. Uh, but it's like, you know, we make it happen. We make it together. We make it human. We make it about the customer. Like, it's like these 6 kind of guiding principles are aligned with P&T, with go-to-market, with ops. Wherever you are in the company, there are examples where, you know, you can live by those principles and show examples of that, but they're not necessarily specific to GTM.

Okay.

What we do that is very specific to GTM, since we're like focused a bit more on, on, on recognition is we have this concept of the elites program, kind of borrowing from Air Canada with elite status type of thing, but it's, it's essentially reps based on their achievements relative to quota earn points. And points are automatically translated into promotions. And the promotions are a combination of a change in their OTE, a change in their title, in some cases a change in their responsibility, and also an equity piece. And that's from feedback that we got over the years of promotions feeling like they were subjectively driven.

Oh yeah.

Weren't necessarily fair. And also, I don't want my managers to think about who to promote. I like that this is systemized as much as possible. Leadership track is a little different, but as far as like ICs, up the ranks. So we've kind of like, I was saying, like we kind of gamified it. Like it's basically that, like it's, and what's cool with that is you can move at your own pace. So people that are burning through the steps can get promoted more, you know, more quickly. And there's no cap, like you can keep earning points and it, you know, kind of like as an elite status, right? And the flip side of that is that that is paired with our performance improvement plan. So it's kind of like, think of it almost as like the, the snake and ladder game of Lightspeed. Like you keep hitting and then you can keep going and it's like very straightforward and it's formula driven. Um, and this idea actually came from one of our leaders. If he listens, Liam Crooks, uh, he deserves a shout out, who worked at Yelp for many years and he had designed something similar there and they have all those levels at Yelp.

Yeah, exactly.

But then on the downside, if you're not doing well, it's systematically number driven. So there is no, like, you get on a PIP based on your achievements. It's, there's no subjectivity to why you're on a PIP. And then I want my managers instead, or we want our managers to focus on spending time not figuring out who should be on a PIP, who should be promoted. but more, all right, like what, like one, once the system flags that someone is trending towards a PIP, what can they do to get that, that person back on track?

Mm-hmm.

So really systemizing the kind of the promotion and, and performance management side of role. Um, yep.

That's really interesting. We, we have something similar at Owner where there's these triggers, like 2 months in a row below 75% or like a certain time horizon below a threshold. Automatically triggers what we call a get on track plan. And the get on track plan's a little different than a PIP. Like it's, there's a ton of manager commitment in it and we're, it's not about filling out paperwork so we can just like exit somebody. It's like a flag to the rep and the manager. It's like, you need to get this person back on track because the rules say that if they don't, then they're going to be exited. So it's made I think the reason I love this points approach and why ours works is it's now not the manager picking and choosing because that really, that has the opportunity to really fray the manager-rep relationship. If it's algorithmic, then it's not, you know, your manager choosing you like over this person to be on a PIP or promoted. It's like, it's really about the system and those two people having this common objective. And so you, you, the manager knows if you've had like one rep below 75, it's like, all right, JD, like we got to make sure, like you're not trending great this month. We got to make sure that we're, we're hitting like 80% or like it's going to trigger a GOT and like, we don't want that. And so it just like makes it so much less emotional. Totally. The, the, the points thing is interesting. Are there, is there any consternation? About like, oh, if your territory wasn't as good, or if like, you know, the situation was different, like, you know.

No, you gotta skip. So, so specific to, to this elite, uh, point system concept, you have to stick to your guns. So it only works if it's like, it's very, it's actually very rigid and it's cookie cutter. Yeah, there's no subjectivity. Like, it's just it is what it is. Uh, there's actually only exceptions if, you know, behavior is like completely outrageous or anything like that. But like, assuming like you're not on the, you know, on the PVP's radar type of thing, like it's like, you know, like it's the numbers are the numbers. You know, I think that's the elegance of it in some ways. Um, and then also, I mean, I suspect it's similar to Astralis.net owner, like at Lightspeed, we, we hire mainly on the younger side, uh, to train the, you know, our, our teammates in like within Lightspeed. So we hire a lot at the SDR, BDR level, and then they kind of grow. Um, and we prioritize more like ideally like industry experience in hospitality or retail or golf and, and, and grit and, you know, and those kinds of character traits. And then we will teach you like the sales system and we'll teach you how to you give a great demo and, you know, and that, that, that stuff. Um, but the elite program goes really well with that approach because we don't hire a lot of senior reps from outside coming in. And as you know, the younger generation loves a fast-paced kind of like progress. So, you know, it's pretty typical for our reps to get promoted every 6 months when they start their career, like every 6 months. They get to the next title, the next step, the next level. And it's like our career GPS kind of maps to the elite program. So like they have, what's really good with that is like when you hire someone, you can say, look, like this is where we're starting. You know, as I was saying earlier, like this is what it takes to be successful. So like the dial and the grind and all that, but look, like this is how you can progress. And it's very clear.

And they have control. I'm sure they love, like, I have total control.

Exactly. And it's like, hey, like if I push, if I continue to push this month, I'm gonna get to my number of points required to get promoted to, you know, the, you know, senior, senior SDR. And then, you know, in order to go from SDR to AE, while you need to reach a certain number of points in your SDR track, and then you're eligible to move to the AE track. And then, you know, same goes with, with AM, account management. So yeah, it's just, you know, would I implement that if I'm a startup with like 4 AEs? Like, no, obviously not, right?

Or if you're enterprise or whatever.

Yeah, in enterprise probably doesn't make sense. But like in our, I think in the owner.com world, it's probably relevant too. Like, you know, as you're building like this massive engine, you have to, I think it's actually, I really think it's served us well. Like, and it's made it very clear. I remember when I got here in the early years, it was all about like, okay, what's my career progression, career GPS, blah, blah, blah. Now it's like, it's clear, like this is what you're— and yeah, so, and I, and it's helped. And then ultimately why we did this is to help with tenure because ultimately the biggest correlation is tenure with performance, you know, kind of like full circle to your question around performance. It's a way to ensure that ICs stay in their role longer and look forward to staying in their role longer. Like the challenge we were having A few years ago, uh, was the expectation that we were creating as an IC was that the next step for my career is to be a leader.

Yeah.

And first of all, there aren't enough seats for everyone to be a leader. If we're all leaders, like, we have a problem. And then second, doesn't mean that you're a great IC that you're a great leader. And then third, uh, I want my best reps to just continue to do what they do well and feel like super valued and rewarded. At that craft and continue to feel like they're progressing in their craft. And so what it's solved for ultimately is tenure and less attrition and so on.

Cool. And so are the points strictly just quota attainment or are there other ways to earn points?

No, this is, so the elite program is entirely focused on quota carrying roles. We have quota at Lightspeed, SDRs, AEs, AMs. Implementation consultants as well are now part of the program and are quota carrying. Other functions in my world, like marketing, you know, RevOps, I have IS, you know, support as well, technical support, customer support are not on a quota-based compensation. So we, you know, they have their own track with their own career GPS, but the elite program doesn't apply to them.

Okay. But the way you earn points is strictly through quota attainment or strictly through quota attainment.

Yes.

So in terms of like this high performance framework, it's hiring is number one, the metrics and cadence, the visibility. We talked about performance management and promotion. I know you're also passionate about enablement as a part of this puzzle. So That's maybe first, first question here before we dive into like, uh, the Lightspeed stuff. Why don't people invest more in enablement? It's a mystery to me.

I think it's because it's hard. It's the same, it's the same reason as to why people have a hard time to invest in brand, in my view.

Yeah.

You know, it's like, hey Kyle, uh, let's invest in like performance marketing and like, let's do more ad spend and you can kind of correlate, well, if we add here, you'll get that. There. I think it's just a matter, it's just harder for folks to wrap their head around, like, if I invest in enablement, this is what I'll get in return, right? It's not as linear, you know, it takes time. And in our world, in technology and in startups, like, people don't like to wait. They're not patient. That's my view, at least if you were to ask me the question, but, but yes, I wholeheartedly love the points you make when I listen to you, which is like, people need to invest in enablement a lot more. And more often than not, if you hired the right person, right? Like, but assuming you hired the right person and they don't work out, it's on you, man. It's like, it's the enablement piece that you did.

Sure.

So what can you do to improve it? I would say for us, we made a ton of mistakes in that department, Kyle. And so, you know, I guess like you asked me earlier, like what I would have told myself, that's another, that's another area. And I'll share maybe a bit of an anecdote. So remember the analogy I was giving you with the fourth floor? So, I mean, we have headquarters, we have offices all over the place, but I gravitate to the headquarters because it's our biggest. We had, we call it the cigar lounge, the fourth floor, because it's literally the vibe is like you feel like you're in a cigar lounge. And at the time prior to COVID, we didn't invest a lot in enablement per se. What we had was sales engineers that were also helping with onboarding new reps and new hires in GTM, but most of the onboarding and training function in GTM, believe it or not, lived in people and culture. So in HR, however, what we did have is everyone in the office sitting all over each other on top of each other. This insanely buzzing energy. You would walk on the floor, the elevator would open, and it's like, yeah, yeah, yeah. The best point where like when people would leave today for the day, like they had a massive headache. Like, I don't know how we got anything done, but the amount of learning from osmosis, the amount of cross-pollination that was happening, like that was basically enablement. And the funny thing is like when COVID hits, because we were such an office culture at Lightspeed, when COVID hit, I remember like it was yesterday, we all freaked the F out because we were like, holy smokes, like how are we going to run this sales team or this go-to-market team with everyone from their house and behind their laptop? And actually for the first years of COVID we absolutely crushed it.

Yeah, because the market was just ripping.

Well, I think for sure the market was ripping. There was demand for a solution without a doubt, but also we carried like that team that had been in that buzzing environment for so long. We had a lot of tenure, like we've a lot of, you had a lot of tenure in that team. It carried us forward, but it was a false positive. But some clients through COVID and, you know, natural attrition, all of a sudden people are like, hey, I want to be a plumber. Like, you know, like everyone was going crazy during that time. Coming up with new ideas of jobs they want to do. So, and then, and then we went through a cycle of hiring and man, did we pay the price. Like then you realize, holy smokes, that was the, that was the glue, right? Like we didn't consciously invest in enablement with like systems and AI and all of these tools that are now out there that I highly recommend everyone considers, of course now, but it was just really the, the, the osmosis that was happening because everyone was together. The journey was kind of like you could follow a customer from lead to signed deal to onboarding to account management. Like you'd walk the floor, like the way it was set up, like was incredible.

The physical environment was enabled.

It was that exactly. So yeah, I hate this, uh, this work from home thing. Just, uh, sorry to be very opinionated on this piece. I'm sure you've had guests that have different opinions about this. I think it's terrible. I think we should all be in the office 5 days a week. I think certainly for folks that are earlier in their career, it's the worst thing you can do. And, um, and actually the other issue is if you say, well, it's only the new joiners that have to be here, but then as you earn your stripes, you can kind of peace out. Well, guess what?

Nobody to learn from.

There's no enablement still because now it's only the newbies in the house. So, so yeah, everyone's here. Like, it's like, there's no, there's no, uh, working from home thing that you have to be here. And, and it goes back to like, yeah, we're not, we're not for everyone. That's, that's okay. Like if you want to work in the public service, there's great jobs out there. If you want to work from home, it's totally cool. Just not, not here because it just, yeah, it doesn't, it doesn't work. Maybe. For more enterprise-focused selling kind of roles and GTM for like really large corporations, you're in a plane anyways all the time.

Yeah.

So maybe it's not as paramount. And then, sorry, it's a long-winded comment on this one, but also just the, the, the incredible things that happen when a lawyer meets an AE.

Yeah.

After having worked on a big RFP or whatever it might be, or a big deal. And this, this, like, I know, you know, but like working on Zoom is super transactional. You're not all these moments. I'm sorry. Like, I know people say they do all these funky things online. Like, it's just not going to happen. So being here, it kind of like encourages people to have those moments where they just go to the cafeteria and just hang out with someone random and then new, new ideas form from that, you know?

Yeah. And so going back to post-COVID, you realized you needed enablement, new hires weren't ramping like you wanted. What did you change? What type of enablement investments did you make?

Oh, we made so the craziest mistakes. We even, we even at some point being a lot more conscious of cost, we, you know, sorry if they're listening, we cut SEs, terrible idea. We did really, you know, bad things there. And then eventually we realized, no, no, we need to bring back a really strong enablement function. We now have enablement leaders for each of our business units with teams under them. We moved obviously, you know, onboarding of new and continuous learning of GTM into GTM. Because as I said earlier, outside of our sales engineers that were kind of like doubling up on that, it was really led by HR. And then obviously we're we invested more in tooling. Actually, in one of your podcasts you mentioned, I think, Kimi Onisivera. So that got me very excited about that. So we're exploring that side also of enablement.

Cool.

And, but yeah, but so now what we've done is, well, first RTO. So back in the office folks. And then second, yes, investing more in documenting, systemizing, tooling. The other thing that we also saw is you want your, I mean, as you move up in the organization, you want the go-to-market leaders to own enablements because there is no finger pointing and it's kind of full circle on the hybrid piece of owning the outcome is something I'm a big passionate fan of. If you just own the task, it's too easy to say, yeah, we're not hitting our targets because our teams are not trained properly.

Yeah.

So, so what we also did by bringing that into the function of GTM is that my, my, my go-to-market leaders, my sales leaders, my customer success leaders, my support leaders, my onboarding leaders own the enablement arm of their craft and their function.

So the enablement person actually reports to the functional leader in that business unit. That's great. Yes. And how do you maintain consistency across the customer journey when, when enablement sort of reports in? Separate?

Well, that's my role. So I mean, my role and a few others like myself, we have to make sure that all this comes together. And so, you know, at Lightspeed, we have first and foremost a specialization at the vertical level or at the industry level. Folks that are on retail, they're just on retail. Folks that are on hospitality are just on hospitality.

Folks that are roll into different GMs, like hospitality rolls into, and that hospitality GM will have sales, CS, and everything under it.

Yeah. They, they own all the, the full go-to-market functions, including enablement in this case. Yes.

Okay. Very good. Very interesting.

Yes.

Cool. And then for tooling, like you're making like LMS tooling decisions, like in RevOps or centrally, everybody's using the same tools.

Yes. So, yes. So. You know, that's where you have to be careful. And that's, that's obviously a challenge when you acquire a lot of companies too. We inherited a plethora of tools, but yes, and we can expand on the playbook of like, you know, post-acquisition and so on. But, but certainly like the, the goal in my role and others like my head of RevOps, my head of IS, there's a couple of functional leaders that sit across all of our industries. And one key focus is we have our, our head of customer experience and our customer innovation hub, Cindy as well. Our role is to drive consistency. So it's like, it's the healthy tension between, you know, we have our wild horses out there in retail and hospitality that just want to run and go and do their thing. And that's great. And you want to foster that spirit, but then also how do we bring it together so that we don't end up with wildly different business units all over the place and all of our geos. So to your point, tooling systems, even our commission plans, like a lot of our structural decisions end up converging to the same structure as much as possible. We leave some level of customization, but like as much as possible, we've learned the, the heavy cost and the heavy burden of not doing that. It's really treacherous, particularly now in the world of AI, right? Like if you just let everyone run loose like that, then forget it. Like you can't implement anything like this. Yeah. Unstructured data everywhere.

Yeah. The, the. The winners of AI are people with like structured businesses and good data and process and documentation. The boring stuff, the boring stuff is cool. And so wait, so there's a central team making like these types of decisions or like, how's that? How?

So those, so I mean, ultimately those teams all report to me, right? So I guess ultimately, ultimately that's kind of like how we bring it all together.

So if you're building commission plans and like you're, you're Thinking about changing a commission philosophy, do all the business unit leaders get together to decide that together? Or like, how does the decision making work?

Yeah, good question. So my head of RevOps owns the, the, the management of the plans from a, from a systemization perspective. And then, and then ultimately my business unit leaders will have opinions. We kind of like bring it all together. We all duke it out and we make decisions, but the decision is always consistency on this specific piece.

Yeah.

Yeah. Like for example, right now we're going through a project to evolve the way we look at commissions because you know what's particular in our industry, which I believe owner, you're not doing that, but keep me honest is so we have a payments piece to what we sell that adds a layer of complexity, right? As far as like, how do you recognize the actual revenue booked? So, you know, that's an example of getting into the realm of like residuals and paying on actuals and things like that. So it's, it's been, it's been an interesting journey going from a pure play software company in 2019 to now juggling something very straightforward with a contract and a contract value and like a monthly annual to you have that, but you also essentially pay for the solution with with payments revenue, which fluctuates, margins, which fluctuate.

Yeah.

Yeah.

Yeah. We have the same thing, same thing at Shopify. How do you, how do you comp somebody on, you know, potential GMV when, you know, that's most of the, you know, Shopify is 65, 70%, uh, merchant, merchant services revenue, which is both payments and capital and all the other stuff. But yeah, you, you, and it's still been the last couple of years, like a massive work in progress, I would say. We're a little more simple in many ways. It's mostly subscription. There's some take rate on it, but we have like a predictive model that tells us what we think the deal value is going to be. And then we just calm people on that. And sometimes it's too high and sometimes it's too low, but like across hundreds of deals that a rep will do in a, in a, in like a 6-year or 6-month period, it all like relatively nets out. And you know, the specific number doesn't matter because the variable number could be off by 25% up or down, but it's just relative to quota. Like we set the, we know the average deal size for subscription plus variable, and then as long as the quotas roll up to something that makes sense.

So you kind of tokenize the value basically. Is that—

is that basically? Yeah. We're, we're, which is, is imperfect, but otherwise you'd have to pay them on like a first 90-day, you know, actual calculation. But what if the something's like not working? And so it's, it's, and then they have to wait, like sales reps don't want to wait to get paid. So we simplify it by just saying like, we're just going to pay you upfront and here's the value. And so one of the other things is like, cause we're on this topic of RTO and culture and expectations. Like you, you also mentioned to me, like you don't believe in work-life balance, which will be controversial to many. So I'd love to hear your, your, uh, your take on it. Yeah.

I mean, again, this is like more provocative statement when I was spilling the perform there, but yeah, I mean, ultimately it's more the concept of saying, and I think you said it too, because it sounds like we're very aligned there, like, you know, you don't, like, don't join a tech company that has the ambition of going from $75 million to $1.2 billion in revenue in 6 years if you prioritize, um, you know, spending time at home and spending time focusing on your hobbies. Like, It's like, just kind of like, like there are a lot of really amazing employers out there that will give you the freedom and the ability to do that. But that's not what we're about, right? Like if, yeah. And like people sign up to be here because they want to achieve like things that I guess on paper are technically impossible, right? Like I actually mathematically speaking, I mean, I'm it's probably even worse as a, as a Quebec-based company, but as a Canadian tech company, like the odds of reaching a billion dollars in recurring revenue are like insanely small. Like actually I'm giving a talk in a couple of full weeks about that. Like the odds are like basically 1 out of 10,000 or 1 out of 1,000 if you want to be generous. So it's like really small. So yeah, if you're going to join an organization where the goal is to defeat the odds, like don't think. That work-life balance is a priority, right? Like, it's as simple as that. No, I guess most people want both.

They're like, no, no, I want—

that doesn't exist. Like, I can— you have— it's like, I like to believe in, uh, you know, that there's gold at the end of, uh, the rainbow, like all of those great things. But, you know, it's like, uh, it's— you have to pick, you have to pick. And it's— and, you know, maybe there's seasons in life, right? Maybe there's a moment in your life where like you really get galvanized behind like a project. And I think that's the point, right? Like that's the concept is like, hey, it's like, don't get me wrong. Like it's important to have a family life as well. Like I'm not, I'm not a masochist here. I'm not a dictator, but you have to kind of like buy into the project. And in order to win at this project, like you have to dedicate a lot of your time and a lot of your energy. And obviously coming from the startup world, I mean, that's what, that's what it's all about. I'm always fascinated by the talk you hear sometimes online or out there of founders that prioritize work-life balance and, but yeah, it's like, yeah, but like, those are like, it's like not going to make it. They're in complete opposite directions. So it's not going to work, you know, it's like for sure.

So that's, that's yeah, it's. It's funny, a lot of this comes from like people want it all. It's like, I want to work at a cool company and get promoted and make a bunch of money and have a liquidity event. But also like, I only want to work 35 hours a week. It's like, well, like those, those things are mutually exclusive. That is, that is oil and water. And I oftentimes say to people, it's like, you can't expect extraordinary career outcomes without extraordinary effort. And maybe if you're way smarter than I am and you have much better luck, and you're just like so much more talented than me, maybe you could like work not that hard and still get promoted a whole bunch and whatever, but it's probably not going to be, it's probably not going to work. And people want to make it a moralistic thing. I'm not saying working hard is better than not working hard, but the work-life balance crowd so often is like, you know, they're anti-capitalism frequently and they make it seem like, oh, you know, like you shouldn't work hard. Like you're a bad bad guy if you work hard and you want people to work hard in your team or company. And it's like to make themselves feel better, probably, but it's just not like everybody can make choices and we can be a psychotic company and like nobody has to join.

But, but like, that's the, like, you can set whatever expectation you want as long as you treat people well and, and, uh, I think that, you know, this whole cheesy thing of saying like, follow, you know, work in what you're passionate about. I mean, like, as cheesy as it sounds, ultimately what it's about is just finding an environment that you really enjoy being in and solving problems into, or just kind of collaborating out of. And then it doesn't feel like work. You are energized from the task and the actions and the problems you're solving versus it's sucking energy out of you. So if you find something that energizes you, then by the fall you'll be like, yeah, like I didn't keep tab on the amount of hours I've been doing this week. I started my career in the public service. I will not name the ministry, but what I can tell you is this, I think like third week in I was told, hey JD, you know, we do things differently here. Like, okay. Tell me. It's like, you don't have to work like this. Like you don't, like you shouldn't work like this. It's like, don't work hard. You're making us all look bad. I'm like, but I like, that's not my intention. I just like, I'm a passionate kind of guy. I'm just like, I just want to like, like just go to the coffee station and wait there for 3 hours. Like I get crazy bored, but, um, yeah, like anyways, I digress, but that's why I think, uh, Tech and being in this kind of industry suits some people, but not everyone. And that's totally okay.

That's totally okay. Yeah. Yeah. All right. I want to switch gears and talk about some of the hard-earned leadership lessons from your career. So one of the things you mentioned is like what you can learn from your to-do list. Curious, what is, what does that mean?

So I started doing that when I was a founder. We were only like 3, 4, or 5 employees and I actually carried this on forever since then. So I have, I have a, you know, it's kind of random and I'm not using any special tool or any AI. Uh, you know, I have a Remarkable that now broke. So now I'm back to like my, my binder, but I have a, I have a to-do list and I have an outsource list. Um, and then pretty religiously at the end of the week, maybe biweekly, I will stare at what was on my to-do list and what I put on my outsource list. And, uh, I guess the point I was making with that comment was like, you learned so much going back and looking at what was on the list. And if you do it consistently over time, like it's actually fascinating. What you put on your outsource list isn't something you outsource, but that you don't own. So the way I approach it is like, if I pass the ball to someone in the organization, I still own it. And I use this outsource to remind myself who I outsourced it to. And then I follow up with that person probably way too many times because I'm annoying for that. But then what you find fascinating is like if that name keeps coming up over and over and over again, you probably have a problem because probably the level of engagement on that side isn't where you want it to be. I know this sounds a little Machiavellian, but I mean, it's just fascinating. So like for anyone who's listening, I encourage you to just like the good old school to-do lists, I have a memory where I remember what I write, so that helps, but it's like going back to it and remembering what was on that list and then obviously making changes to what you spend so much time on, right? Like, it's like my biggest challenge is I take on too much and my, and it's a, time is a very rare commodity. So finding ways to optimize the time I dedicate to things so that I can create space is just so critical. So yeah, so that's what I meant by that. And it's kind of a full circle to the high performance piece that you asked earlier. It's really fascinating to see, I think in organizations, it's the challenge in the cancer as you grow is people end up owning the task and not the outcome. And it's like making sure that, you know, it's like that good old Spider-Man meme where everyone kind of points in different directions. It's like making sure, yes, like, yes, you are passing the ball. Yes, you're outsourcing something to someone, but ultimately you still own the outcome of that pass.

Right.

So anyway, so like interesting themes to riff on that piece, but yeah, that's what I meant by that.

Yeah. What's from doing this review, what's, what is an example of something that you're like, I'm doing, this is in my to-do list too many, too much. I need to like offload or stop doing, what are those lessons?

Yeah, exactly. It could be this keeps coming up and up and up and it's like someone else in the organization is better qualified to do this thing. So I should move that to the outsource list. So my, my mental model is it starts on my to-do. Then I realized this is something that keeps coming back on my to-do and either I keep it because it makes sense that I own it. So that's fine. Or ideally I outsource it so that I can add new things on my to-do list. If I outsource it, I stay, I follow up religiously on where that thing is. And eventually if it gets to the outcome that we are all hoping for, that makes me realize, okay, well now I can systemize this. What used to be on my to-do list religiously now can be in my outsource list forever, so to speak, because I know that The way we set it up or in the person who owns it or the team that owns it can do it and they can run with it. And so I don't have to worry about it and keep going back to it. And I guess it kind of comes back to what I've had to change because I'm such a, like I over-prepare, I'm a control freak. Like I'm, I mean, I have, I have imposter syndrome in the role that I'm in. So I compensate by like being very like maniacally focused on some of these things at times. But if I'm not able to get some of this stuff off of my to-do list, then it's like, I'll never be able to live another day type of things like that. I'm able to organize it in my head.

Yeah. One more personal productivity question. What are the most important meetings on your calendar each week?

Yeah, I think it's, this is more a reflection on like, as your organization grows, it gets very easy to lose perspective. And so for the revenue leaders that are listening out there, and hopefully you're crushing it, you're killing it, and you keep adding more reps on the board or more wins on the board and ultimately more revenue and maybe more people. But again, maybe you're killing it with AI and you don't need anyone.

Good for you.

But either way, it's very easy to fall prey to the process of the organization getting bigger and bigger. And I think ultimately what you should be focused on at all times is like, you're always hiring, you're always speaking to customers. And you're always doing skip meetings. And it's like, that's my— like, when you look back at the end of the week, did you, did you meet someone, whether if it's internally in your organization that you think could be like a good candidate for future growth, or did you meet someone externally? You know, over the years, because we've had to grow, we've had to work with a lot of agencies to help us hire leaders and so on. I found actually so much value in just like keeping, keeping that rolling and kind of always meeting candidates, even if in the end, maybe we're not necessarily gonna hire that person. So like the concept of like meeting people with the intent that, you know, you will want to, you, you will need people as you grow. And so always kind of like the hiring mode on. I, I always look back in my week. It's like, did I have a meeting that was setting up for new hires in one way, one shape or form. Did I have a meeting that was tied to like a customer issue we have or a customer problem or a customer just being happy and providing feedback? And then I spent a lot of time and it's not, I hope my team doesn't think, feel as it feels as threatening. Like I generally care and I like, I love meeting people throughout the organization wherever they are and doing a ton of skips. You learn so much from that.

Yeah, for sure.

I think as a revenue leader, like those 3 categories, like just look at your week. Like, did you meet a customer this week? You know, did you meet a potential candidate to hire? And did you do a skip meeting? It's easy real quick to get lost in strategy and Zoom meeting galore on process and lose sight that you, you know, you haven't done those 3. And then soon enough, if you're not doing those 3, then you've lost touch of what's really happening on the ground.

Very much agree. I did a skip level this morning. I, uh, had a customer meeting a couple of days ago. I got a, got, uh, plenty of talent meetings this week.

So I, I think those are, well, you saw that you have a secret weapon with this podcast. I mean, you're like, it's, I think that you cracked the code. Yeah.

I'm certainly not doing this to make money because there's none of that, but from a talent brand building perspective, that's always why I've done the LinkedIn thing. And then it just snowballs. Like I had a bit of a following and then people invited me to speak at stuff. And then you have speaking, speaking stuff makes, makes content. And then you bring that back into LinkedIn and then, you know, now it really is snowballed in this podcast. There's more about that. It's actually me, like not having mentors. I've never really had mentors that I spend a lot of time with. There's a lot of smart people that I'll like text or call about stuff, but this is like my mentorship at scale, just talking to people like yourself who are a couple stages ahead in, in the businesses that they run. So it's, uh, but the talent, the talent stuff is great too. Okay. Last question before we get into this rapid fire. How do you think about building trust at scale?

Yeah, that's been actually my number one challenge as a, as a leader that I've had to work on. It's our, and actually it's our, you know, she's gonna laugh if she, I don't know if she'll listen, but if she listens to it, it's our chief people officer, Shivani, who gave me that book. So I come, I told you, I come from diplomat parents. We're Canadian diplomats. And so I'm, I'm, I somehow, I care a lot. Like I've, I very much care about what I do in my job. I'm really passionate, but I wasn't the clearest. And so she gave me this book, the Radical Candor. And it came from just observation from my peers, my other leaders. It's one thing to care, but you have to care and you have to be clear. And so that's my style of leadership that I'm working on all day, every day. Like the clear part used to be my biggest challenge because I was such a diplomat. I was like, no, I don't know if it's like the nicest guy in the room type of thing, but it's just like I would go. Very, I guess, diplomatically and softly and between the lines, you could read what I meant. And that's like, no one has time for that. So I think in the last years, I realized you build way more trust if you pair the caring with being super clear. Doesn't mean you have to be an asshole about it. Like, there's like being direct in a good way and being direct and just being a straight up annoying colleague. But that's the piece that I meant there of like, how do you build trust as you grow? That served me well. And I continue, like, I continue to work on that. Like, I'm saying like, I kill it, but that's the piece that I would recommend for people that have my character traits. Maybe others have no issue being clear and being candid and maybe it's the other side and that's okay too. But yeah, that's that's basically my take on that one.

It's funny because when Radical Candor first came out, I actually was like slightly negative on the book. And because I found that people used it as an excuse to just like be an asshole. And it's like, hey, JD, like, you know, I really care about your success. Also, you're no good at your job. And it's like, no, no, that's not the right thing. And then she did a second edition and addressed that point upfront. And I was like, oh, this is like the point I've been trying to make about this book because I found that folks were like really misapplying it and misapplying like, no, no, no. Like the care thing has to be real and it doesn't mean just being overly direct. And because people can't hear a message if they are in defense mode. And so there is something to the packaging that is important, but being direct, but like communicating it in a, in language that they can interpret that doesn't make them feel threatened. Because as soon as there's ego threat or we're in an ego defense mindset, then like nothing goes in. Zero.

To your point. And so like, hence, yeah, like people will see through the fact that you don't really care, right? Like, and so like, it doesn't work. It doesn't work if you're clear and direct, but yeah. People don't feel like you care. That, yeah, that, that, that's—

All right, let's move on to quickfire so we can get you out of here on time. What do you think separates a great CRO from just a good one?

I think the, the role of the CRO has changed, uh, at least in my relatively young career still a lot over the years. And so I would say answering that question today, the modern CRO, let's call it this way.

Mm-hmm.

Uh, what is someone who, you know, it kind of goes back to what I said earlier, like you need to be able to understand every instrument of the orchestra to play at the great symphony type of thing. I think CROs over the years have moved up in ranks and were a great typical profile, great in sales, right?

Mm-hmm.

But the, the, the function that CROs lead more often than not is more and more now the entire go-to-market journey. And like you are ultimately responsible for retention. You're ultimately responsible for the bottom line. And so, you know, I think what really differentiates a great CRO from an average or maybe bad CRO is their inability to really understand the full journey and the different crafts that have to come together. And they tend to over-index on the thing they're really good at. And that's okay. I mean, everyone has a strong, you know, skill that they leverage but then underinvest in really understanding the other side.

Yeah.

I mean, I've seen that over the years too. And so, yeah, that would be my answer for sure.

What's the most common advice you give to like first-time VPs of sales that you're mentoring?

Kind of, I think we touched on it a bit, but like maybe to, you know, to highlight like the key ones for me, first one is like own the outcome. Like really, really own the outcome. Don't, don't, don't own the task on the outcome. Like now you're a VP, right? You're a VP in the organization. You need to be able to take a problem which will be multifaceted by default. It's not just a sales issue, right? Or it's not just a customer success issue or support issue or churn. Like, okay, we have a lot of churn in the organization. Like the reasons why, you know, our customers are churning, there will be, it will be multi-threaded. And so you need to be able to take this, this challenge that we need to solve and own it and get everyone to get to that outcome. And so a lot of VPs I find as they move up in their career struggle to make that step. Like they'll take the approach of like, well, you know, like I own this task. I'm the VP of product marketing. You know, I did my job, did it all, passed the ball over and like, like, you know, we didn't really solve the, you know, the churn problem, just to continue to riff on that. And product marketing has a, you know, has an impact on that, you know, amongst other functions. And if for whatever reason you were tasked to do that, or you're on a team tasked to solve that problem, own the outcome. I think the other is, you know, as I said earlier, kind of be a blue-collar leader, roll in the mud, like never forget where you came from. I like, I don't know, these are all kind of like cheesy sentences, but Going back to getting the details and understanding like how the cogs of the machine work and how people are actually doing their job and walking a mile in their shoes so that you have the right level of empathy. And when you're going to roll something out, like you'll understand whether if this is actually realistic or not. It's hard to do because as you ruin your career, then you're, you kind of lose that perspective. So it's super, super important to go back to that.

Yeah. Makes a lot of sense. What's the hardest lesson you've had to learn?

I think it's a lesson I keep learning. So it's not like there was like, I've lived it and I've now solved it. But certainly my, the hardest lesson I continue to learn is just scaling myself, like just like not taking on too much and finding ways to continue to grow. While just not, not taking on everything. And, uh, yeah, that's, that's certainly something I'm still struggling with every day. But, uh, yeah, I would say that, that would be one. I would say maybe more, uh, practically speaking, tactical, as far as like revenue leadership is concerned, we've had a lot of projects over the years that either worked or failed because we didn't necessarily, uh, create a team that was hyper-focused on that thing. So I think over the years, what you find is like, if you are, you know, if you're listening and you're like, hey, I'm going to start a new motion or I'm going to start, you know, this, this new project that we've never done before as far as like how we go to market or how we build awareness or how we onboard a customer or customers or like anything you're trying that's new and that will be hard to do, but that is fundamental to your success. Often what, what folks do or what organizations do is that they'll task a few people on that project, but it's like 10% of their job or like 20%. And then they have other, other things they have to tackle. Um, like the typical, I guess, basic one would be like a manager owning inbound and outbound and you're trying to, you're not, you're out, you're starting outbound and this person is leading inbound. Let me bring it back to like the most simple example that will fail epically. Like I've seen it enough times now, I'd tell you it will fail. Like it's just not going to work. Everyone's going to gravitate to like 80% of their day job, or they're going to gravitate to the easy thing that's already part of the culture that's already well documented. So specializing teams is critical. And we've made, you know, on that front, we've made a lot of mistakes over the years, like not doing that. So I would say that'd be more of a tactical kind of like thing I'd share.

Makes sense. What's the best thing you've read in the last 12 months?

So I don't read a lot, to be honest. I listen a lot. So I'm a podcast listener through and through, and I like to listen to audiobooks. But one book I re-listened to, and I know you're going to be like, this has nothing to do with revenue leadership, but I promise you there are parallels. I'm a big fan of Trevor Noah. If you, anyone who's listening who wants to get into it, Born a Crime is a fantastic book. I grew up in Ivory Coast and Morocco, so I always felt like I was an outsider. So personally, I like, there's some parallels to my personal life that I like and he's so funny, but I think it's such a great book that teaches you resilience and just being optimistic, which ultimately is critical, you know, even as a revenue leader. So, you know, I was thinking of something that not someone would expect from a podcast like this, And listening to it instead of reading it is the jam, is the way to go because Trevor Noah is the narrator and he's freaking hilarious. So Eileen Ringland, it's an old book now probably, but I recommend doing that.

Very cool. That's awesome. Well, JD, this was great. I was excited for it and we hit a ton of good stuff. We really got through it. So shout out to Guillaume for the intro and this was a blast. Pleasure.

That's it. Check out VASCO, folks. It's a great product to run your RevOps operations and your data. And thank you, Kyle, for having me here. And I'll continue to be an avid listener, but, and I won't listen to this one, but I'll listen to the next guest. That's for sure.

Yeah. Yeah. Awesome. Thanks, man. Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes and be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.