Jimmy Tristovski on Turning HR into a Scalable, Data-Driven Business Function

00:00 Jimmy: People always have the misconception — “oh, we don’t practice our business as a family, we’re high performance like sports teams, like athletes.” I’m like, look, there’s pros and cons to both. But what I’ve seen at the end of the day is in a family-run business who treats people like family, they generally have high employee experience. And if you have a high degree of employee experience — a variable that I generally measure in people analytics — you’re going to have a successful business. You see increased customer satisfaction, profitability, earnings per share, and growth. Fact.

00:44 Joe: Hello everyone. This is the Next Moves and it’s a series of interviews done with people who have built incredible companies and awesome careers. I’m doing it for the simple reason that there are so many moments where I’m sitting in meetings in my job as a recruiter talking with a CEO or a founder or a member of their team, and they’re talking about the choices that they’ve had in front of them and how they considered them, and then as they made them — the impact and what happened. And I’m just thinking to myself, this is so valuable for people because we all get stuck. And hearing how people plan their next move and the move after that, it can help us make better decisions. I’m going to be honest — sometimes it feels like people make very logical, calculated decisions. And all the other times it feels like they flip a coin. And I think we can learn from both those scenarios and the outcomes they got. So without any further delay, let’s talk to my next guest.

01:39 Joe: My guest today is someone who I find super interesting. His name is Jimmy Tristovski. And Jimmy is interesting because he is a data-driven HR and people leader. A lot of people say they’re data-driven, but Jimmy is going very deep into this. He’s helped run fast-growth tech company HR and people functions, and he does it in a very disciplined and effective way. I look at him as an architect behind the cultures that we have in some of the best companies in Toronto and across Canada. You’re going to hear about how this former Windsor kid dreamed of engineering, tried his hand at MMA, and then found his calling in HR and leadership. Using design thinking and hard numbers, he was able to show HR as a profit lever and not a cost center. I’m going to dig into his playbook for building talent systems that drive growth, the way that he attacks problems that he uncovers inside of organizations and how he prioritizes them, the tough lessons he’s learned when culture starts cracking, and why data really needs to be looked at as a secondary source alongside your gut feel — because they can play off each other and if they’re working together, you get a much better outcome. So this is for anyone who has stared at an empty talent strategy and tried to figure out how do I build this effectively, and can I scale this organization without breaking it. He’s done it more than once. So without further ado, here’s my guest Jimmy.

03:16 Jimmy: Thanks, happy to be here. That was a fantastic intro. I’d like to open with a question and then we end with the same question — if you had to boil everything down to one principle that drives a successful people strategy, what would it be?

03:32 Jimmy: The way that I look at it — when you jump into these types of opportunities or if you’re in this profession — is that employees are customers and work is a product. Full stop. That’s how I look at it. Whereas classical HR teams don’t do that. We need to essentially optimize our product — which is our work — in order to provide value for our customers, which is our employees. So we need to operate similarly to how a product or engineering team would operate. This requires a really big change in mentality and culture and the general skill set for practitioners. Going back — a lot of businesses still do this and a lot of HR professionals still look at themselves this way — HR is a classical procurement or admin function that’s built to be a servant. It’s structured as an input to production. Whereas some new-age departments and some practitioners I know operate as a value-added line of business. The leadership is valued as a partner that creates economic value — even if it’s predominantly savings. So managers in these departments have to be proficient with people-centric design thinking, which is bringing innovative solutions to life by understanding how employees — which is our customers — think, feel, and behave. Whereas classical HR does not really follow that path. It’s very much dedicated to that procurement and administrative mindset. In order to be relevant and competitive as an industry-leading organization, those teams have to adapt. There’s still a need for the classical elements in HR, but they’re generally smaller functions in my opinion.

05:52 Joe: So for people to know where you’ve come from — born, raised, school, sports, decisions, how you were wired, where you come from?

06:07 Jimmy: So like you mentioned, grew up in Windsor — Windsor boy. And I think you were also raised in Hamilton but went to teachers college in Windsor?

06:15 Joe: That’s right. That’s what it was.

06:15 Jimmy: So you know the area. My dad immigrated to the country in like the ’70s, so he was in his late 20s. A lot of influence comes from my dad. You hear me reference him a couple of times. What he accomplished in his life is not quite Arnold Schwarzenegger level, but it’s pretty epic. He played professional soccer in Germany. He was a mechanical engineer. He’s a marathon swimmer — he still holds the record in Lake Erie for longest marathon swim, which is pretty cool. Worked for Ford for a long time. Was a musician. Got us all into music at a young age. We had a family band growing up. He was a loving disciplinarian — that’s what I call him. Just beastly in nature. That rubbed off on us. So me, my brother, and my sister were always very motivated. We had a good role model. Shout out to my mom too — she was also a good role model in a different way. But early on I always liked tinkering and problem solving. I gravitated more towards math and science at a young age. I know I was joking about being the chess savant, but I played a lot of chess too when I was young and did a lot of mentorship and charity for the Great Canadian Chess Challenge growing up. My brain was always wired that way. Always in cars, always into athletics, just because of my dad and my brother — I just gravitated that way. So when it came to high school, all my subjects were mathematics: calculus, physics, enriched chemistry, biology, computer science. My mindset was I was going to go into engineering — something similar to my dad’s or my brother’s profession, because he’s quite a bit older than me. As I was going into university, things were changing. The recession back in 2008. And I wasn’t sure if there was going to be opportunity for me in the automotive sector or in engineering. And the more I thought of it as work, I wasn’t sure how much I liked that. But I still had this part of my brain that’s always mathematical, analytical, looking at problems, trying to understand them from the root cause and solving it that way. The thing in the back of my brain though was like a leadership seed that was just trying to grow. And I always saw that in athletics — doesn’t matter what sport I was playing. You mentioned MMA but a big part of my life was also soccer, basketball, most sports at school, individual sports like swimming, tennis, and MMA. But when it came down to the team sports, I just naturally gravitated towards being the on-field general — that type of persona.

09:33 Jimmy: The first time I got into recruitment and was exposed to that was actually in university, before I actually started it. There’s this organization called Guatemala Hope — they’re a non-profit building houses in impoverished areas of Guatemala. Their challenge was actually getting volunteers to go over there because at the time there was a high crime rate in the areas where they were building. The building materials would sometimes be compromised. So it was trying to actually get talent to join them. That was when I was first exposed to it. Because they were a small non-profit I had an opportunity to play a leadership type of role. I really liked that. So going into the main workforce, I’m like okay, I have a couple of niches here — one of them is a technical mindset, but I love the idea of leadership and I love the idea of impacting businesses from a people perspective. How can I do that? HR and people was the obvious route, but everywhere I interviewed and places I saw, most businesses looked at HR as pencil pushing — not really a business-optimizing function. How do we change that? I’m sure you’ve been exposed to that sentiment too, like a decade ago or more. My whole niche was — how can we make it more scientific and how can we make it a business optimizer? So I started doing that throughout my career.

11:22 Joe: So let’s go — one, two, three, four jobs that you take. The first one that you take is what?

11:31 Jimmy: Well, the first one I took — and some people might have gone down this route — I was actually involved in a pyramid scheme that I didn’t know was a pyramid scheme.

11:42 Joe: Were you at the top or at the bottom?

11:42 Jimmy: I was at the bottom. It looks very different from the bottom, from what I hear. It’s kind of hilarious now looking back on it, but it exposed me to Toronto because I wanted to move here. That was the job. And I started to see red flags — within two weeks I’m like “okay, this is clearly not an actual job.” Red flags like “oh, we pay you monthly at the end of the month” and “you’ve got to generate 150 leads for this and that.” I thought this was supposed to be a little more consulting. This is like back-end sales. Anyway, after that job I got into a boutique agency because I had a bit of that experience in the past. I also had a lot of sales experience — I worked at Radio Shack, which is now The Source by Bell, for about six and a half years. Had experience as assistant manager, doing a lot of sales, wireless devices, packages. But after that got into the boutique agency. Gave me good exposure to the Toronto market and a lot of the different partners and industries we worked with. This was also at the start of the startup boom, which is where I started to meet a lot of contacts. And you know on the agency side you start to meet tons of people. From there I went to CareerBuilder — I wanted something a little bit more engaging, a bit more advanced with more responsibility. You’re familiar with CareerBuilder?

13:23 Joe: Absolutely. They were one of the top brands in that space.

13:28 Jimmy: Yeah, 100%. They were doing some really great stuff with SaaS back then. It was a mix of running a 360 desk but also consulting at the same time. You’re finding your clients but also helping engage them. And I had great opportunities to work with companies from Vancouver, Chicago, New York.

13:50 Joe: What I’m curious about is you’re doing this work at CareerBuilder. You land that role coming out of recruitment in an agency — how do you dovetail that or move it into a role as a consultant at what was at that point one of the best HR talent tech companies around? How do you make that move?

14:15 Jimmy: Great question. I think it was the way I positioned myself. Regardless of coming from an agency, a lot of people have misconceptions about agencies and the work required to do that, especially if you’re coming from a small one. I think they really appreciated the book of business that I was able to build. They knew that I understood not just this small niche of recruiting but how the world works, how business operates — budgeting, forecasting, appealing to the customers you’re actually working with, how do you service them afterwards, how do you solve their problems? I think they just saw me more as a problem solver with a niche in a scientific field or at least a scientific mindset.

15:12 Joe: So you end up working with some very well-known brands — theScore, I remember it when it was starting up and scaling up. I know Top Hat quite well. And a series of these well-known organizations including PolicyMe. You’ve scaled teams now in these companies from a few dozen to over a thousand employees. I have to ask — how well defined is the company’s ask of you when you’re joining these companies?

15:52 Jimmy: I would say it depends on the organization. There were also companies that I worked with in a consultative capacity — like Wishabi, which is now Flip. Back in the day, Hyperwallet, which got purchased by PayPal, GM — big names, small names. But I would say a lot of people don’t always know what they want. It’s true for when they’re looking for consultants and also when they’re looking for employees, but they’re a bit more cautious and hesitant when looking for full-time employees because they don’t want to make a mistake. Generally speaking, I would say 80% of the time it’s not well structured and I don’t think they see the potential of what it could become and how important these people functions are to overall success. Now I use theScore, and especially early-day theScore, as an example quite often because it’s one of Canada’s unicorn tech companies that had a massive exit. But they really knew what they wanted. They had an amazing leadership team and at least had the structure of how they wanted it to operate — more driven by goals and a mission, a clear vision of what needed to be done, but also the trust and the autonomy of “hey, we hired you for a specific reason, we know your track record, we know your ability to collaborate with teams cross-functionally, solve problems, come in and help us do this so we can become this massive billion-dollar company from a humble startup.” So I use them as an example of one of the companies that did know. And even with them they didn’t know everything, but they had amazing leaders who would ask the right questions and allow you to help them scale truly. They saw you as a partner. That’s one of the key ones — this is a partner who’s a business optimizer, not a cost center.

18:13 Joe: Let’s talk about that because they knew what they wanted — but what was that business when you joined? What was the industry and what space did it start in and what did it evolve into over time?

18:26 Jimmy: So it’s a sports media and betting company now. You go on your phone, download the app — it’s a media app that gives you all the scores, news, updates, chat channels. It became like Canada’s sweetheart in the sports area. It evolved into a sports betting platform similar to the bigger names like DraftKings, FanDuel, etc. And then the N casino. All those combined. Prior to that though, it was a television network. Now me and you — because we’re a bit more, let’s say experienced —

19:05 Joe: Experienced, let’s say that. That’s a good word.

19:05 Jimmy: We remember the television network days, where they were like a sports net. They had sold their media entity off to Rogers. And they were left over with the digital assets — Rogers didn’t acquire those. So they basically built this — the first free phone app I had which was on a BlackBerry — and I remember seeing it back then being like “oh, this would be a cool kind of company to work for.” This was years before I had the opportunity to work with them. But then I worked with them as a third party when they were around 100-110 people, helping scale the engineering side and the product side more particularly.

19:56 Joe: There’s an idea of growth and there’s an idea of doing it properly. And it sounds like according to you they did some things well. Give me the one, two, three that they did well as they were scaling.

20:10 Jimmy: So we started as a more humble team — around six people, I think. My leader Sally Ferrell, big shout out to her. She was an encyclopedia of HR knowledge — it was like whatever you asked her, boom, she knew it. So it helped that you had someone who was a knowledge master in that area. Combined with critical thinkers and problem solvers, it was awesome. On top of that — she and the founders, it wasn’t just her — it was the founders, the Levy family, who were amazing leaders. Love that family. They did a lot for me. They had the mindset of you’ve got to build an amazing culture and culture is everything. If you look at the most successful companies — you can name a lot of the big organizations like the Googles and so on — but if you look at other successful startups and scale-ups, they have a common ingredient, and it’s a wicked culture.

21:23 Joe: It also sounds like there’s a prioritization at the highest level for culture, which is like they’re telling you to build this as opposed to you saying we need to build this. They’re pushing you as opposed to you pulling them.

21:33 Jimmy: Correct. And the thing was my first time at theScore was the first time I would say I was so refreshed and said “oh wow, this is what coming into a place looks like that is already well-established with a culture.” Their challenge would now be scaling that culture as it grows — at 100-175 people I knew every single employee’s name, what they did, what they liked — and we had that camaraderie, that collaboration. Everybody was involved. The C-suite didn’t have egos. Like I was saying earlier — they treated you like family. And I think it was because the nature was that they were a family that started it. Some people always have the misconception that “oh, we don’t practice our business as a family, we’re high performance like sports teams, like athletes.” I’m like, look, there’s pros and cons to both. But what I’ve seen at the end of the day is in a family-run business who treats people like family, they generally have high employee experience — if they’re doing it the right way and extending that outward. And if you have a high degree of employee experience, a variable I generally measure in people analytics, you’re going to have a successful business. You see increased customer satisfaction, profitability, earnings per share, and growth. Fact. They did it the right way, all the way from the top down. Same mindset, excitement, motivation, passion from everybody. Very refreshing coming into that. So now it’s like — okay, we’re 175. How do we maintain that at a thousand?

23:21 Joe: You’re counter to the popular narrative — “we’re not a family, we’re a team.” And you’re going the other way. I think it’s great that you did, and you backed it up with what you will see inside of these organizations. So my question within that — how do you overlay people analytics in each of these roles, and let’s get a 30-second definition for it.

23:42 Jimmy: How I look at it — others might define it differently — I want to start with the purpose of it. And the purpose is to drive insights to maximize that employee experience variable, which has a whole ton of other layers underneath it. How I would define it is a deeply data-driven, goal-focused method of studying people, processes, functions, challenges, and opportunities at work — so that you can elevate these processes and systems to achieve business success through driving insights to maximize employee experience.

24:34 Joe: I want you to give me a very clear example of the practice and implementation of it at any of these companies.

24:42 Jimmy: Yes. So the first thing I’ll usually do when I enter an organization is understand their current state. For that I use two types of models. Generally speaking I’ve always managed or been the head of talent functions. There’s a model called a maturity model — and similar to what engineers or technical people would know, it’s like AWS has a maturity model to implement their systems. There’s a similar type of method for talent. A maturity model with a lot of different functions attached to it — sourcing, recruiting, employment branding, recruiting culture, compliance, and so on. Where are you on a scale of one to five? One being super ad hoc and reactive, five being fully optimized. By doing a deep dive and understanding where you are, that helps you understand where we currently are, what we’re missing, what challenges we have, what we need to put in place to address those challenges to reach our business goals. Because you’ve got to tie them to the business goals at the end of the day.

Same thing on the data side. When we’re talking about people analytics specifically, there’s also a more classical data maturity model that I use — on a scale of one to five, where one is ad hoc, very initial, data used sporadically without consistent process, exists in silos, heavily relying on spreadsheets. How do you get to the area which is fully optimized and transformational — where data is embedded into the culture and you’re driving innovation and continuous improvement? Think real-time analytics, automated insights, using AI and machine learning capabilities, a culture of experimentation, AB testing, proactive. It’s a completely different level.

27:30 Joe: Give me an example of those data points that you’re collecting. If we standardize our processes, what are the actual measurements when you’re further up that maturity model curve?

27:42 Jimmy: I’m not going to go into the full maturity model because that could probably take a whole podcast — that’s a part two.

27:48 Joe: Part two. Yeah, we can do something like that.

27:48 Jimmy: In terms of some metrics — let’s say we’re at a startup, founders haven’t even heard of people analytics and are asking “what is this, how can we benefit from it?” You’d start with something as simple as the recruiting function. Time to fill, source of hire, etc. As you get a little more advanced, you start to calculate cost per hire. How much does this cost? Then you can tell a better story of why if we’re taking 50 days to hire a role instead of 20, it’s costing you a lot more.

28:37 Joe: I have a friend who says what he’s good at is eating payroll — “what are your key skills? Well, I eat payroll really well.” But it’s true. When you first start, you’re losing money. In our business you look at the first year as an investment in an individual. You recover some or all of that in year two, and after that people can become fully economically profitable. But you’re looking at what are the key inputs into that. Do you see that thinking when you step into companies?

29:04 Jimmy: No. I haven’t seen it. Shout out to PolicyMe though — we can get to that stuff later, but they have the right mindset and vision. Which is great. I came in and the culture is amazing already. Good culture of documentation, good systems in place, open mindset, good collaboration. And they appreciate what I’m able to bring to the table in terms of that people analytics structure. I think they’re already seeing it. But in the past — you can start as simple as what I might be doing now because we’re a bit earlier in the journey, to what we had at theScore at one point. Which is basically what we’re talking about — you have all these managed dashboards, you’re a big partner with finance, you’re forecasting headcount, calculating all these costs, calculating salaries. You have an employee-in, employee-out type of measurement. You’re measuring capacity. That was one thing we did. If you want a specific example on the recruitment front — a big challenge for companies is always “why are you hiring so many people?” And if you don’t have people analytics or data to show, you’re going to have a tough time pitching why. But when you have something fully mature, you can show — okay, for each one of these departments, here’s the rough time to hire, we know X amount of days for this type of position, here’s what the funnel looks like. You need, for example, 100 interviews at the recruiter level to get down to one person signing — because you’re following this funnel and trying to see the conversion at each stage and then trying to optimize that.

30:55 Joe: And there’s a lot of optimization effort before a headcount is pulled and before a headcount’s given. Let’s optimize the conversion in the middle of the funnel so you have more people.

31:06 Jimmy: Exactly. So then they finally see like “okay, Jimmy or Joe is onto something.” We’ve got to hire 50 people and the average time to fill is X. But the average top-of-funnel metric — how many people we need — is averaging at 100 interviews per role. 100 interviews times 50 is —

31:33 Joe: Quick math. That’s 5,000.

31:34 Jimmy: That’s right. 5,000. That’s a lot of man and woman power to do that. We need agents out there. AI agents.

31:49 Joe: We’ll get to that too. But that’s a big story to tell.

31:49 Jimmy: So then it’s like — okay, they need recruiters, but how many? Here’s this capacity model, Mr. or Mrs. Executive. This is how much time recruiters spend on each task on average. We have it in a model that we’ve built. We’re able to plug in these jobs, organized by department, and it’s an automated calculation that says Joe has X amount of time to take on an additional job. If anything goes into the red in this tool that we built in-house, that means Joe no longer has time. So if you’re assigning him a role, we will not be able to fill it at the expected time to hire. It will now take double or triple the time. Do you want to risk having a product leader, designer, engineer, salesperson, finance person delayed 90 days?

32:46 Joe: No, Jimmy, I don’t.

32:48 Jimmy: Right. Okay, great. So I’m going to hire another recruiter. And the same goes for the people and culture side, employment brand, and so on. You can get very advanced with these metrics. That was my whole point in telling that story — where are you in this journey, what’s important, and how is it going to relate to business goals? We weren’t just doing those things for vanity.

33:15 Joe: So I have a question for you then because this ties to outcomes that founders are thinking about all the time. And you’ve said this to me — I want you to explain it. Some founders think they just need superstars on their team and that’s an oversimplification.

33:34 Jimmy: Very much so. An oversimplification. I usually give an analogy for this. Hopefully some people are athletes — if not, I think a lot of people will still know it. 2004 NBA championship was between the Detroit Pistons — my team — and the LA Lakers. And even people who don’t follow basketball know the names: Shaquille O’Neal, Kobe Bryant, Karl Malone. Depending on what age group you are, they were a team of all-stars. Every single one of them, including their bench players, were on the All-Star team that year. The Detroit Pistons were not all-stars. If I drop some of these names, people are going to be like “who?” — Ben Wallace, Chauncey Billups, Rip Hamilton, Tayshaun Prince. None of them. They had a really good coach, a really good leader, but they were role players. The way the Pistons built out their team that year — or over a couple of years — was to fill certain gaps where they had challenges. Whereas the mindset of the Lakers was “we’re just going to get the best people who cost the most money because they’re all stars.” But they skewed heavily towards the offensive side of what all-star looked like for basketball. Whereas Ben Wallace was rebounding, defense, blocking — nobody could touch him. Rip Hamilton ran the floor like nobody else, would always create openings. You had three-point shooters, good leaders. The point being — the Pistons destroyed them. It was a sweep. And that goes back to how you build teams. If you just look for all-stars, egos can come into play — too many chefs in the kitchen. You want to hire based on competency and you need to understand where your gaps are in competencies. If I have a particular gap on a team, when I hire my next role or budget for the next role, I want to solve for that challenge.

35:48 Joe: Given that we’re building these teams constantly at Clarity — we’re building these leadership teams and we’ve historically operated mostly in finance and now are aggressively being pulled by our clients into HR, people, talent, and operations. When I say operations, it’s broad depending on what kind of company you’re in. My question is — the HR and people function rolling up to the CFO or COO versus the CEO. Does that affect your view of whether that organization values it or not? Or does it just mean you need greater context around everything?

36:36 Jimmy: That’s a really good question. I would say one factor depends on how united that C-suite is, because I’ve seen in the past for companies I’ve consulted for — and even sometimes in some of the places I’ve been full-time — there’s not always generally a unity behind the direction and the vision. If one person has more of the decision-making authority at the end of the day and they don’t value the people function, you’re going to have a tougher sell. The biggest mistake that HR practitioners and people departments make is they can’t communicate how our function optimizes the business and essentially creates more profitability, more growth, more opportunity.

37:37 Joe: I think it’s an excellent answer. And I want to actually say — this has been an amazing conversation. It felt easy, right? We just ripped through things.

37:47 Jimmy: Okay.

37:48 Joe: I always want to make sure that people know they can find you on LinkedIn and connect with you.

37:57 Jimmy: LinkedIn is the best spot to see everything that I’m doing professionally. That’s where I encourage people to go and follow me. And obviously the PolicyMe page now — we’re going to take this company on a rocket ship to the moon.

38:13 Joe: To the moon. That’s the plan. All right, man. Well, thank you so much for your time.

38:16 Jimmy: Appreciate it, Joe.