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SPOTLIGHT: Untangling Tech Debt and Finding Product-Market Fit with Russ Mikowski of SurePeople | Russel Mikowski, CEO @ SurePeople

26m 54s

SPOTLIGHT: Untangling Tech Debt and Finding Product-Market Fit with Russ Mikowski of SurePeople | Russel Mikowski, CEO @ SurePeople

This episode of Top Line Spotlight features hosts Sam Jacobs and AJ Bruno interviewing Russ Makowski, CEO of Sure People, a company disrupting the traditional psychometric assessment market. Russ explains that legacy tools like DISC, Myers-Briggs, and Hogan are typically reserved for small privileged groups such as leadership teams, limiting their value because insights are unavailable in the moments that matter most. Sure People addresses this through its proprietary PRISM self-assessment, which is designed for universal organizational deployment and feeds a people intelligence data layer that integrates into everyday tools like Slack and Zoom. Russ describes joining Sure People about a year ago, recruited by an executive search firm specifically for his CRO background rather than prior CEO experience, a pattern he says is increasingly common for companies that are under-commercialized. He discusses narrowing the company's ICP to earlier-stage technology companies of roughly 50 to 2,000 employees that are remote or hybrid and prioritize retention and data-driven decisions. He also shares his approach to leadership during transition, emphasizing transparency, communication, and a "disagree and commit" philosophy. Finally, Russ credits mentor Colin Day, founder of iSaaS, for instilling a people-first mindset and disciplined SaaS focus. The episode closes with a light discussion of PRISM archetypes.

Transcription

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Speaker 1Welcome to Top Line, the podcast for the best founders, operators, and investors in B2B tech. Every week, AJ Bruno, Asad Zaman, and me, Sam Jacobs, will break down what's important for you to know to be the most well-informed professionals in the market.
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Speaker 1Hello, everybody. Hello, everybody. It's Top Line Spotlight, a nice little place to be. Top Line Spotlight. You know Top Line Spotlight. It's that mini. It's that mini segment of the Top Line podcast released every Thursday, each episode featuring a one-on-one interview between us, the hosts of Top Line, and an incredible operating executive, leader, CEO, founder, visionary, influencer that's talking about a problem that they've solved in the last year to year and a half. And what a time, what a time, ladies and germs, to be talking about solving difficult problems in an era of unprecedented volatility and uncertainty. A.J. Bruno, the CEO of Quotapath, Sam Jacobs, and I, that's me, Sam Jacobs, have Russ Makowski on the show. Russ is the CEO of Shore People. He's a founding member of Pavilion when it was known as Revenue Collective. He's a longtime operating executive and CRO in the HR tech space. And also, when he's not a CEO, he gets on the other side of the table, and he is a retained compensation consultant for Pavilion. He helps hundreds of. executives every year negotiate better deals with their companies thanks to Russ's support. So he gives back. He supports the community. He's an incredible leader and partner. And Shore People is an incredible company. Russ, welcome to Top Line Spotlight.
Speaker 3Thanks for the kind intro, Sam. I'm excited for the conversation.
Speaker 4Russ, do you remember your first event at Revenue Collective? Was it a dinner?
Speaker 3I think it was more of a mixer. If I recall, at the Smith, perhaps?
Speaker 1That was. Maybe it was a breakfast. You might have had breakfast with me at the Smith. It may have been. It's so long ago.
Speaker 4Didn't Revenue Collective have like koozies, like swag koozies that they like handed out at the mixer?
Speaker 3At breakfast as well.
Speaker 1We had handwritten note cards. All right, Russ. Well, first of all, AJ, how are you?
Speaker 4I'm great. I'm great. Yeah. We. We may have filmed a Top Line yesterday where I said I'm fine. And now today, I'm actually. I'm actually really doing well. I'm excited for this conversation. That makes me happy.
Speaker 1When you're doing well, I'm doing well. That's how I feel about you doing well. All right. Russ, did I forget anything in your bio? Anything that you. No, I don't believe so. Where are you from originally? Where'd you grow up?
Speaker 3So, I like to say upstate New York, which, you know, anyone in the North. In the Northeast seems to use to clarify that they were born north of Manhattan, not upstate as far as, like, Syracuse or Rochester, but Orange County about an hour north of New York City.
Speaker 1Where Tuxedo is, right? Or Tuxedo Park, you know where that place is?
Speaker 3Not far at all, yeah. I played Tuxedo sports teams in high school athletics frequently.
Speaker 1Did you ever go to the place where they've got, like, all of the. They've got that old. Old tennis. Like, they have. It's like a haven for racquet sports around the lake. Anyway, I don't need to belabor the point. You are the CEO of Sure People. Tell us about Sure People. What does the company do? Why is it important?
Speaker 3Yeah, so Sure People is disrupting a traditional psychometric assessment model. We own proprietary IP to a psychometric self-assessment called PRISM. It's actually the most robust vehicle of its type on the market today. And we're. You know, traditional psychometric assessments like DISC, Myers-Briggs, Hogan can be really valuable when an individual is looking to learn more about themselves. They're often reserved for small privileged groups like the leadership team at an executive off-site or, you know, a group of high-potential employees that the company wants to provide a, you know, kind of coach-led session for. But the lack of universal deployment across an organization carries with it kind of like a limited. value for these assessments. The intelligence that's derived from them is not available in the moments that matter most in the flow of work. And, you know, that's what we're here to address, right, by really looking at a go-to-market model that encourages deployment across whole organizations, democratizing access to these psychometrics. We've built this really cool people intelligence data layer that can then be used to fuel within the flow of work tools that we already use. We use and communicate within, like, Slack and Zoom. It's really cool stuff.
Speaker 4Yeah, Russ, I took the assessment in December. The first thing I noticed was the UI of the. especially on the mobile app, like, it actually makes it feel like you're going through an experience. I don't know if that's just the color palette or whatever, but I was, like, clicking through it. I'm like, oh, I actually feel good answering these questions where most of them, they're just like these surveys that are just, like, put in front of you and just like, ugh. You got to click through. But you all did a great job on the front end of making it feel like you have to read the question to make sure you engage. Was that. I'm sure that's an intentionality on your part, right?
Speaker 3Yeah, definitely intentional. When we think, you know, again, to the traditional assessment world, not too long ago, we were taking these things with, you know, Scantrons and number two pencils, right? And the results were metaphorically, sometimes literally, stuffed in your desk drawer. They're in a manila folder, unaccessible to anyone outside of a human coach walking you through every element of it. And, you know, the cost that that carries with it is one of the reasons that, you know, these assessments have been targeted at smaller privileged groups. The intelligence gained from those things was not easily accessible. We really focused on educating people in exchange for the time that they've committed to answer these questions and doing so within a UI that's, like, very comfortable, familiar. We're inviting and hopefully encouraging people to come back and use the tools again, not only to learn about themselves, but also others within their organizations.
Speaker 1Russ, how old is the company? Tell us a little bit about the history of Sure People and how you came to be CEO.
Speaker 3Yeah, so Sure People's been around for about 10 years now. We've been working with, historically, primarily larger Fortune 500-type businesses and big healthcare, big banking, professional sports, organizations use our product, coaching, development, surprise, surprise, is important, and athletics. And I was brought on about a year ago to think about taking the company to the next stage commercially and really zero in on finding maybe a more focused ICP, think about trying to address some of the technical debt that we've amassed over the years and build out more of an integration-oriented, data product strategy, as opposed to how we'd operated historically, which was as more of a platform tool set. And that's a transition that's still underway, but we're making nice progress with it.
Speaker 4Were you an advisor to the company before you joined?
Speaker 3No, I was not. I was recruited by one of the typical exec recruitment firms. And what I'm realizing is pretty frequently the case these days, even when talking to pavilions. I'm advising about negotiations as a lot of these CEO searches conducted by companies who maybe haven't hit the second or third stage of growth are targeted on folks who've more recently been CROs in a particular space, hopefully with a little bit of an exit track record. And this particular company slash investor set slash recruiter was looking for someone who hadn't actually been a CEO before. So this is my first. At scale CEO gig.
Speaker 4Were you looking for a CEO gig?
Speaker 3Absolutely not. I wasn't looking for any gig, to be honest.
Speaker 1I think that's so I can just see. I can see how relevant your comment is, because there's clearly so many companies, probably I would imagine with product led seat founders that, you know, built something that really was probably very useful. But maybe under commercialization. Under commercialized, under monetized. I can imagine. I don't know the origins of short people, but I imagine it's like some academics and I I can see why a CRO background would be a good profile for leadership at this stage.
Speaker 3Yep. And I think, you know, when you've had that kind of experiential set rising up through the leadership ranks, a certain level of commercial acumen applied to decision making that's often based on focus and defining things like the ICP and thinking about metrics like CAC to LTV ratio. Is something that maybe doesn't come as naturally like you inferred, Sam, to folks from more of a product or academic oriented background, right? So, yeah, that doesn't mean that we as leaders who came up in the commercial discipline don't have our own blind spots, right? And the assessment certainly tells me about mine every day. So I continue to focus on filling that.
Speaker 4Russ, that's one thing that I get asked a lot about being a sales leader by trade of just from a product standpoint. How have I learned or worked on my acumen as it relates to the product or coming in to share people? How would you say what was your own like self-evaluation of you coming in to understand how products deployed, how it works versus what's been kind of your learning and growing during the last year plus on that front?
Speaker 3Yeah, so I think I have a relatively unique. But advantageous background in the sense that I've had a lot of exposure to product as an advisor and kind of like a tinker on the side. So I write some code. I've definitely built things before. I'm relatively familiar with user testing. However, you know, there's a difference between being able to creatively come up with an idea and effectively communicate with some slides or a really basic prototype to agree. I think that's a really important thing. structures to ensure that we have the right people, the right number of people, the right people thinking about the right things. And I think it's really important as you go through changes like that to be very transparent, communicative, make sure the team understands why we're making the decisions that we are. We don't always all agree about everything. We like to operate with a modicum of disagree and commit philosophy where it's necessary, but we certainly listen to everyone's opinions. We're small enough that we still can, and we frequently talk about our direction. I think
Speaker 4a little bit about my own, I mean, we're having this conversation, but it's like a back and forth in some of the own messaging that I have in my own company and how I think about it in terms of similarly, like the ICP and TAM, and then bringing it back to the customer value that we're delivering. It feels like your delivery in terms of what you're doing as well is really important. I think it's a really important thing. Like you're tying those two things together for the organization and that makes a ton of sense to me. What, Russ, what
Speaker 1did you choose? So I understand the theory of like, you know, you could be focused on seven or eight things. We should focus on one or two. So what'd you choose? Like, what did you, what did sure people decide to focus on? Tell us your ICP.
Speaker 3Yeah. So we're focused on earlier stage technology companies primarily. So 52, call it 2000 on the high end employees, right? Companies that are very likely to be remote or hybrid have more, you know, asynchronous communication challenges than other companies. Retaining great people is tremendously important to them. They understand the value of data and making decisions. They're probably wasting incredibly important employee time and unnecessary meetings. We help to solve all those challenges and problems. And that doesn't mean that we don't have something for, you know, certain larger customers who have, you know, have a certain way of doing business, but that's where we're focusing most of our marketing and product build at this point.
Speaker 1Cool. Russ, we're, we're just about at the end of our, of our time together here on top line spotlight, but what we do like to do is pay it forward a little bit. Find out what, what inspires you could be podcasts. You've listened to recently books. You've read people that you think we should be aware of that have influenced you. Who comes to mind?
Speaker 3Well, that's like really such a great question. There's so many, I've been lucky to have some great mentors and work alongside some tremendous leaders. Colin Day, who founded iSIMS, where I was the head of sales from about 40 to 200 million and growth is, you know, one individual that comes to mind. He always kind of preached this philosophy of building with one code base and operating under what he called a pure SaaS philosophy, even when it meant, sometimes saying some difficult no's to prospects who were interested in trying to commandeer the roadmap. And, you know, he, he always carried an org chart, a printed version of the org chart everywhere he went in the office. This was pre COVID when everyone's there every day. Right. And that was like, not only a symbolic, uh, kind of association to how important he felt his people were, right. When everyone saw the CEO carrying this org chart, he was like, I'm going to do this org chart around into every meeting. But he was also the type of individual who was always thinking about like where people could be moved or promoted or learned into a new realm that would be better for them and the company. Right. And I think I've learned a lot from that. I don't carry an org chart around with me, but I'm definitely thinking about the fact that in my opinion, the most important element of building a great company is attracting and retaining great people and removing obstacles to let them do their best work.
Speaker 1Awesome. Uh, Russ, if folks want to learn more about sure people or get in touch with you, what's the best way to reach you?
Speaker 3Sure. Sure. People.com. You can click to a book of consultation, contact me directly at Russell at your people or on LinkedIn.
Speaker 1And what's your, what's your prism archetype before we go?
Speaker 3So I'm a catalyst, which means a combination between powerful and versatile, like bigger picture thinker looks exactly like that. Yes. Is that yours, AJ? That is mine.
Speaker 4That's mine. So we
Speaker 3have a lot in common and probably need a really strong, uh, right hand man or woman who is great on the like precision side, right?
Speaker 1You're reading AJ's mind. He was literally talking about that yesterday.
Speaker 4A hundred percent, literally a hundred percent. That's what I need now has someone to like, keep me focused, controlled, but also operationally has like all of the things done. And honestly, if I can get three of those people, then I'm in good position.
Speaker 1I'm a guardian. What do I need?
Speaker 3So a guardian is a really interesting combination between amiability and precision with a little bit of power sprinkled in as well. So you're kind of like a, uh, we would call it like a three discipline specialist as opposed to a two. Um, I think guardians need people who are going to be able to do that. So I'm a guardian. I'm a guardian. I'm a guardian. I'm going to be able to go through details and keep plans on track as well. Does that sound like, like, yeah, I need people
Speaker 1to use around yourself. Yes. I also need people that, uh, understand the difference between being nice and being kind so that when I'm not nice, they know that I am still kind. Well, a guardian used to be a tough and tender, right?
Speaker 3Yeah, exactly. Literally explain. That's how he is sometimes.
Speaker 1That's what they have to say. It's okay. He's a nice guy. Um, Russ, thanks so much for being on top line spotlight. A great job on sure people were super excited to support, uh, your growth. And if you're not, if you're out there, go to sure people.com, take the prison self-assessment and figure out what type you are. And without further ado, uh, have a great, have a great day, everybody.
Speaker 4Thank you guys. Appreciate it. Thanks, Sam.
Speaker 1Come out every Sunday. If you like what you heard today, subscribe. So you never miss an episode, leave a five-star review and share it with your friends. Don't forget to join our top line Slack channel to connect with us and discuss the topics we cover with other listeners. Click the link in the show notes. Lastly, if you're interested in joining pavilion, you can learn more about membership at join pavilion.com forward slash membership. Thanks again for listening.

Podcast Summary

Key Points:

  1. Russ Makowski, CEO of Sure People, is a longtime operating executive and CRO in HR tech and a founding member of Pavilion (formerly Revenue Collective).
  2. Sure People disrupts traditional psychometric assessments like DISC, Myers-Briggs, and Hogan by democratizing access across entire organizations rather than reserving them for privileged groups.
  3. The company's proprietary PRISM self-assessment feeds a people intelligence data layer that integrates into tools like Slack and Zoom to deliver insights in the flow of work.
  4. Sure People has operated for about 10 years, primarily serving Fortune 500 companies in healthcare, banking, and professional sports, before Russ joined a year ago to lead its next commercial stage.
  5. Russ was recruited for his first at-scale CEO role specifically because of his CRO background, reflecting a trend of investors seeking commercially minded leaders for under-monetized companies.
  6. The company narrowed its ICP to earlier-stage technology companies of roughly 50 to 2,000 employees that are remote or hybrid and value data-driven decisions and retention.
  7. Russ emphasized transparent communication and a "disagree and commit" philosophy when restructuring teams and making difficult strategic decisions.
  8. He cited Colin Day, founder of iSaaS, as a key mentor whose people-first philosophy and discipline around pure SaaS focus shaped his leadership approach.

Summary:

This episode of Top Line Spotlight features hosts Sam Jacobs and AJ Bruno interviewing Russ Makowski, CEO of Sure People, a company disrupting the traditional psychometric assessment market. Russ explains that legacy tools like DISC, Myers-Briggs, and Hogan are typically reserved for small privileged groups such as leadership teams, limiting their value because insights are unavailable in the moments that matter most. Sure People addresses this through its proprietary PRISM self-assessment, which is designed for universal organizational deployment and feeds a people intelligence data layer that integrates into everyday tools like Slack and Zoom.

Russ describes joining Sure People about a year ago, recruited by an executive search firm specifically for his CRO background rather than prior CEO experience, a pattern he says is increasingly common for companies that are under-commercialized. He discusses narrowing the company's ICP to earlier-stage technology companies of roughly 50 to 2,000 employees that are remote or hybrid and prioritize retention and data-driven decisions.

He also shares his approach to leadership during transition, emphasizing transparency, communication, and a "disagree and commit" philosophy. Finally, Russ credits mentor Colin Day, founder of iSaaS, for instilling a people-first mindset and disciplined SaaS focus. The episode closes with a light discussion of PRISM archetypes.

FAQs

Sure People is a company disrupting traditional psychometric assessments with its proprietary PRISM self-assessment. It democratizes access to people intelligence across whole organizations and integrates insights into tools like Slack and Zoom.

Russ Makowski is the CEO of Sure People, a founding member of Pavilion (formerly Revenue Collective), and a longtime operating executive and CRO in HR tech. He is also a retained compensation consultant for Pavilion.

PRISM is Sure People's proprietary psychometric self-assessment, described as the most robust vehicle of its type on the market. It aims to make assessment insights available in the flow of work across entire organizations.

Sure People focuses on earlier-stage technology companies with roughly 52 to 2,000 employees that are likely remote or hybrid. These companies value retaining great people, data-driven decisions, and reducing unnecessary meetings.

Sure People has been around for about 10 years, historically serving Fortune 500, healthcare, banking, and professional sports organizations. Russ was recruited about a year ago to take the company to its next commercial stage, sharpen its ICP, and build an integration-oriented data product strategy.

Russ is a Catalyst, a combination of powerful and versatile, which reflects a big-picture thinker. AJ Bruno shares the same archetype.

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