#20: Oleg Rogynskyy, People.ai

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. Wow, you are just gonna love this conversation with Oleg Roginsky. Oleg is the founder and CEO of PeopleAI, People.ai. They use AI to automate contact and customer activity data to help sales and marketing teams win. It's his second startup. His first was Symantrea, which was sold to Lexalytics in 2014. I was introduced to Oleg through Robin Matlock, who is an alum of this podcast, from Startup to Grownup. Thank you, Robin. And also Andrei Aksarod, who is the former CTO of People.ai and a longtime friend and colleague. And we had such an incredible conversation. Oleg is so thoughtful and very intentional about the way he has thought about building his company. We talk about specific tactics for board management and how he sort of thought about getting the most out of his board and building his board and when he thinks about taking their advice or not taking their advice. We also talked a lot about what he calls hiring way out of his league and how specifically he approaches his hiring process and how the company has adopted techniques to make sure they have the right people and maintain a high bar and cohesive culture. And then we absolutely talked about his network. Oleg is really well known for having an extensive network, and he talks about how he thought about creating his network and how he uses his network and how he keeps in touch with people, which is not so easy when you are a busy startup founder. This is such a rich conversation. I know you're going to love it. So please enjoy this incredible conversation with Oleg Roginsky. Oleg, welcome to the show. I'm so happy to have you today.

Thank you for inviting me, Alisa. Excited to be here.

Great. So, you know, Robin Matlock introduced us and I spoke to Robin Matlock, also an alum of From Startup to Grownup, the podcast. She's on your board and she originally introduced us. And, uh, I asked her about some questions that I might ask you. And she told me, Oleg is Ukrainian. This war is very personal for him. And he is spending all his spare cycles helping bolster resources in Ukraine. You've been working with Elon Musk. You've been raising money. You've worked to get your employees out of Ukraine. I really can't even imagine what it's been like for you. So first of all, how are your family and your friends in Ukraine?

Well, I managed to get my parents out in time. But a number of my friends and extended family are still there. A few of my friends are on the front lines. A number of them are in the government. And my family is basically in rural Ukraine hiding from what's going on. But they're still around. My third cousin was actually killed in action a few weeks ago. He was in military. So it is what it is. But overall, it's been obviously tough, but also it's been pretty empowering to see how individual citizens like myself are able to make a difference.

Yes, I can definitely understand that. I'm really sorry to hear about your loss, obviously. And I mean, I can imagine it's been so emotionally taxing for you and for everybody involved. I guess I'm wondering, how are you thinking about your time and sort of managing your focus on the business as well as dealing with the things going on around you, the obvious things in Ukraine going on around you?

Yeah, absolutely. Uh, so the first couple weeks, obviously, uh, it was very distracting, and, uh, I was mostly focused on the Ukraine stuff. But over time, uh, the work that I've been doing kind of subsided because all of the basics were figured out, all the processes were structured, and then it started needing less and less of my involvement. Uh, now I'm mostly, uh, fully back with my focus onto the business. What really helped in the thick of it is how people stepped up. My team came to me with, hey, how can we help? And I'm like, look, I actually found myself with a lot of leverage in terms of helping Ukraine, but the best thing you can do to help amplify that leverage is by pulling harder so that I can get my time to focus there. If the business is going well, I can afford to spend more time there. And so, it was really inspiring to see how the team got everything together. And even though they were— it was distracting for them too, they started producing results at significant scale without me spending as much time on the business. The team stepped up. That really helped.

Yeah, I can imagine. So, unburdening you so that you could take your time and focus, which I totally understand. Now, do you still have employees in Ukraine at all, or have they all been evacuated and out of the country?

So, we managed to persuade majority of people to leave the country about a month before with their families. A few people went back and joined the fight, but that was voluntary and, like, we were supportive if that's their choice.

I see. So, are the employees who are now, you know, evacuated and they're elsewhere, are they still working? I guess what I'm wondering is, how do you keep people productive and focused even though they're either in the war zone or they're just adjacent and they've left their homes. How do you think about that?

Productivity is almost back to 100% for those. And there is an interesting reason for that. They all spend weeks literally sitting all day long and reading news. At some point, your brain wants to get away from that. And so folks a couple of weeks since they came back and saying, can you give me some work so I don't spend all the time reading news?. And I can even see this by my own dad, who I flew in from with my mom, flew in from Ukraine, and they were reading news and they were miserable. And I literally, as this living with me right now, I literally started giving them a lot of work around the house, and just by being busy, they became happier. So that way to use work as a mean to distract yourself from something like this, is definitely a positive thing for them. And productivity, I guess, in, in some way is, is keeping up.

I think that is so telling about the human condition. I mean, one thing about work— and this is why I became a coach in a corporate context and working with companies— our work is satisfying, our work is meaningful when we give ourselves to it. And to your point, it takes your mind off of the things going on around you that you can't control, and you can really make a difference with the things that you can you can control inside of work. So, it can be very satisfying in difficult times.

Yeah. I mean, to be honest, I discovered something about myself. Like, no matter how positive or negative of a day I'm having, I'm working with my chief of staff who is helping me plan some of my day and kind of where I'm spending my energy to sneak in a couple quick wins into my everyday. And it just like, no matter how small those wins are, Getting them done early creates a very different experience in a day.

Now, Oleg, if I step back for a minute, you're a second-time founder. Your first company was Symantec. Is that how you pronounce it? Mm-hmm.

Yeah.

And, uh, that, that applied to machine learning and artificial intelligence at scale in solving the challenges of analyzing and categorizing massive amounts of content from texts and emails for the legal industry. And you had a successful exit. You sold that company back to your prior employee, Lexalytics. So, pretty good. Not bad. And I'm wondering if you look back now, what are some mistakes or lessons learned from that first experience in building a startup, which I don't think got as big, far from it, as People.ai, right?

Mm-hmm. Yeah. Uh, we sold it about 30 employees or so.

Yeah.

Uh, and the lessons I learned are that market size is everything. You can control for your product. You can control for your team, but you cannot control for your market. And that also goes for market timing. If you're too early to market or end up in a small market, or even worse, you are early in a small market, which we were, there's not much you can do there. The best thing you can do is park this technology with an acquirer, etc., and let things kind of play out. What's interesting is 10 years later, or was it almost 10 years later, all my technology that I built for sentiment analysis is still powering actually way more companies now than it was back then because the market maturity happened and the market expanded. So that timing of not being too early is really, really important. And same with People.ai. I think we're a little bit early for the market, and now the market is finally catching up, expanding, and We're getting inbound phone calls for our staff continuously, which is great.

Yeah, that's amazing when you see that finally kind of catch on. Oleg, I asked Robin and also Andrei Aksarod, your prior CTO and a longtime friend and colleague of mine, I asked him, I asked them both, what are your superpowers? And they both said that one of your superpowers is to build an incredible network. And Robin actually said that you're on a text relationship with like all of the Silicon Valley greats. So I guess I'm curious. When did you realize that building a network was so important?

That's a really good question. Back in Montreal days, when I was building Symantec, I focused on building a network and I realized how limiting Montreal network was. It was really difficult to spend your time with people who can make a difference. Because there was not enough of them. And the goals, the aspirations of most of the people were not scaled. And so when I got to San Francisco and I got the first taste of Silicon Valley network, I realized kind of the sky is the limit there through knowing the right people. And that's when I got really serious about maintaining, building keeping the hygiene of the network and making sure all of that is, uh, something that becomes like the baseline skill set.

Yes, the baseline skill set for you of having, of having a network. How do you go about it? Because you came to— you came from, I think it was from Boston to Montreal to San Francisco, and here you are. You don't have any family in San Francisco. You're all by yourself. How did you start? Like, what, what specific things did you do at first when you were building your network? Because there's a lot of founders who don't necessarily have a network, haven't thought about building a network, but need those really step-by-step tactics on how to get started?

Well, we can talk about tactics, but also it's all about being an interesting person.

So, I love it.

We have a hiring philosophy. We call it ICED. Stands for ICED with triple C. Stands for intelligence, character, coachability, curiosity, enterprise experience, domain knowledge. If people think you're intelligent, you have good character, you're coachable, and you're curious, they will be adding you to their network. So it's about controlling for those, uh, it's about always doing your homework and always being prepared. You should never be in a place where you don't know who people are and you cannot ask a number of insightful questions and spark a conversation that will be interesting for them. Nobody wants to talk about themselves. People want to talk about stuff that's interesting for them. With enough homework, you can figure that out. Another piece that is really important is creating mechanisms that remind you about people and building a hygiene around acting on those mechanisms. I use as simple of a tool as email snoozing. If I have an interesting conversation with you, and there's an email from you, I will— and like, the conversation is over, I'll snooze it by 3 to 6 months, and then when it pops back up in my inbox, I'll have— I'm sure I can think of something to reach out to you. Obviously, you have to be very judicious about who you do that with, but more than once it has happened that an email pops up with my inbox from snooze with someone who exactly is needed exactly at this time.

What a great tactic, email snoozing. People don't talk enough about email snoozing. I think it's so great. And I think your point about the mechanism, I know for me, I'm always scanning news articles, right? I'm always kind of reading and just kind of, it just comes to me naturally. Who would care about this blog or who would care about this podcast? So I think scanning the horizon is also helpful. But I'm curious, like literally when you first started, can you think about the first people you reached out to? Did you do cold outreach? Were you introduced? Like, how do you kind of get started? Included in this process?

Yeah, it's always about pulling the string of introductions. Uh, that's, that's something that is big in Silicon Valley, which is the, the art of getting introduced.

Yeah.

Uh, and I'm religious about double opt-in introductions. Uh, there's very few things that will piss me off more than single opt-in.

Oh, I know, I hate that. Yeah.

Uh, but on the other hand, I also reward people in their homework. So when someone approaches me through a warm introduction with the formwork that was done correctly, I will definitely spend time with them. Yeah. And so first introductions, I guess, my business associates or customers from the early days lead that to a number of coffees and interesting conversations, lead that to who else should I know? And, and things unfolding. Another thesis, just making yourself relevant to what is top of mind right now. So like Ukraine is an easy example, obviously, right now.

Yeah, for sure. Are there other examples? I guess I would love to know, like, do you have one really amazing networking story? Like, oh, I can't believe I had that conversation with that person, or I ran into somebody. I listened to a podcast and I think you were like dining next to Mark Zuckerberg and his wife. Like, But I'm just wondering if it's a story that kind of encapsulates introduction to person in your network.

Well, the most recent one that comes to mind is when the Ukraine event started, Andriessen Horowitz put together a first group of about a handful of CEOs who had teams in Ukraine in a WhatsApp chat, but by making it interesting and relevant, and I stepped up and kind of became the shtick of the show, just broadcasting the news and having insightful conversations there. The group grew to about 150 CEOs with who is who and have household names reaching out to me privately after that and saying, hey, really want to help on the Ukraine cause. Didn't want to say anything in a public forum, but how can I be helpful? And We engage CEOs of $100 billion companies into Ukraine cause through that group. And obviously that's a part of networking right there.

Yeah.

And, uh, it's all about also doing what you said you're going to do.

Yes. Yeah. Being the kind of person people want to be connected to. And I think also what you're saying is kind of stepping up and being proactive in a leadership capacity and putting yourself forward. So people then want to talk to you. So I'm sure that you get a ton of advice from them, and also I'm sure you get a ton of advice from your board members. I'm just curious, how do you think about when you get advice from board members, whether you should take it or not take it? Like, what's, um, what is a time that you got advice from your board and you kind of realized, oh, I'm gonna have to— I'm gonna have to pass on this one, I'm gonna have to tell them that's not a good idea? Like, how do you think about that?

Ah, that's a really interesting question because through the years of working with the board, I learned that I wish they knew everything. They don't always. They're humans, mere humans like all of us, right? So what I started doing is I actually started tracking on my end, just the notepad, all the things that they and myself are pounding the table about. Like, there's one thing is just to give some tactical advice. Another one is like, no, I think you should do it the following way. And again, another reminder, once a year I review that notepad and actually score who was right, who was wrong on each one of those.

Wow, very rigorous.

Yeah, and to be honest, that was very insightful.

I'm sure. What did you learn from that process?

Well, that one of the board members I had pounded the table on 5 items really hard and was wrong on 4 of them. They just, nobody knows at the point, it sounded like the right thing to do, but in hindsight, obviously 20/20, but wrong. And so what I learned from that is it is important to listen to the board. But the buck stops with the CEO. And the CEO has to make the final call. And you cannot expect the board— the board is relying on limited information from the business, as well as wealth of experience from hopefully similar situations, but very likely different. And so you have to take them their advice. But you have to make the final call, or else that's a road to nowhere.

Hmm, that is really hard, especially for young founders to accept to deal with, I I think there is a sense of like, you know, I thought my board knew. I've worked with plenty of clients who actually wish they had been more judicious themselves. Did you have to learn that yourself? Did you used to sort of take everything, like all their advice, as correct? And it's only recently that you've more gained that perspective that you just shared?

Yeah. In the beginning, I was listening and executing on the advice. It took a certain volume of that advice and execution to notice a pattern that not everything works out the right way. And I make plenty of mistakes myself, especially when I don't listen to— so it's about the balance. Yeah, but it's also about just knowing that the buck stops with you. It's not about the ego, it's about responsibility. It's my responsibility to make this business successful. It's their responsibility to help me, but if I fail, I fail.

And coming to terms with that attitude.

Yeah.

Yeah. I think that's really powerful for sure. Now, as you've built your board, have you thought about specific skills you want to add to the board? Has it been sort of organic? You know, sort of how did you come to the, to the comp— the combination of the board that you have right now?

It is really important to be thoughtful about board design. And I came to this after having some really good things, some really not so good things, um, kind of work out on the board level. It is really important for the CEO to be thinking about the most strategic challenges that will be happening year to 3 years out and pre-positioning the board with the best experts possible to help them address those challenges. So, uh, I knew at some point marketing pipeline cover is going to be a conversation for us. Therefore, we have Robin, and she's been helpful there. Thus, the CEO also needs to be able to fill in their own gaps, or their own soft spots with, with board skill in a mentorship capacity, not in a, here's what you should do capacity.

Right. That's well said. Is there an example of one of your board members who kind of fills in for some of your soft spots and what that is, what those are?

One of my board members, Will Griffith, has very good sense for product and very good sense for using product to accelerate growth. But more importantly, what's really his superpower is ability to refocus me back on the long term.

Ah, yeah. In what way? How does he do that?

Every time we're talking tactical, he says, great, but here is why I invested in you. So let's talk about that.

The direct approach.

Yeah, that's great.

That's really great. And when you think about managing your board, do you have— I guess I'm curious, like, do you think that the— that you report into the board, or do you see yourself as kind of the leader of the board? How do you sort of think about that relationship?

So that's in transition right now. Initially, it was I report into the board. That's at least the attitude that I had. And that's the wrong attitude. I am on the board just like them. And that transition needs to happen as you're building out the executive team. And then the executive team needs to bring in business performance in front of the board, which I am a part of. And that transition is very, very important to do. It took me some time to figure that out. And it also is important to be declarative about the transition with the board because on the other hand, the board can be playing two roles. Hmm. There is one role of inspection and governance, which is not the biggest value add of the board. And report into the board means you'll be inspected and governed by the board. While the other role, which is much higher value-add, is something that only actively managed boards get to, from my experience, which is kind of brainstorming and coaching. The board is not managing CEO, the board should be coaching CEO. And it's up to the CEO to establish the boundaries and the desired mode of operation.

Right. I love what you said that you need to really declare the transition. I think that when you're making a transition, especially as a CEO, you are the CEO on day 1. And then all the years— how long has People.ai been around? Is it—

More than 6 years now.

More than 6 years.

6 and a half.

But your title hasn't changed. Your role's changed, but your title hasn't changed a lot at all. So I'm curious, both in terms of the transition with the board, but like on a podcast, I heard you talk about how your job actually, the job you actually have, changes, you know, every year, every 18 months. Talk about what that's been like for you and kind of what you've seen specifically in the change in your job over the past 6 years.

Oh, wow, that's a big one. So, initially, it was do everything.

Yep.

So that's Series A, getting to Series B, then it was start hiring people and still do everything, like start having mid-level executives and still do everything. So that's why you have, you get your VPs, VP set, and, but it still requires hand-to-hand combat in terms of scaling the company. The big switch happens to the CEO role. In the growth stage when you start scaling up. That's where you hire the real executives. And once you hire those real executives, you now need to transition from fighting with them side by side to being their coach on the field. Actually, you're no longer on the field. You are the coach off-field while the executives are on the field with their team. And that transition needs to happen on like what, Series C, Series D, and that transition allows the company to scale further because the executives you hired are the ones that are, that know what the scale looks like. You don't as a CEO, or at least if you haven't done it before.

Well, that, I have so much to ask you about that to sort of double-click on that, you know, Of course, I work with so many founders and they go through this transition and it's really hard for them because what happens is they hire their first employees and their first executives and these people they're in the trenches with and they got them to where they are and there's a lot of loyalty there. And at the same time, those are not the people who are going to kind of make the journey to stay in the executive level because to your point, you need people who've done it before. But how do you think about that as the CEO? And how do you kind of get over just like the emotional, the human emotion about it?

Well, it sucks to be losing early people. They were there from the beginning, but that's the only way they will be successful as well. And you have to be very vocal with them from the very beginning that there'll be one day, everybody has an expiration date. Including me, and there'll be one day when the expiration date happens. That's hard. But then on the other hand, uh, you have to also be thinking about it from a shareholder perspective. The best thing for them as shareholders is to bring in leadership team that is able to scale up and move fast. Yeah, so that's something that, um, I've seen over and over as, as early employees are departing at year 6. Year 5, etc., uh, the new folks who are coming in materially accelerate the business. Yeah. And unless properly actively managed, there'll always be ego of the early employees that will be hurt, and that's where the business gets slowed down as well. So there's a lot to unpack there, but being open about this from day one, which in some cases we did a good job, in some cases we didn't, always operating above the line and always operating per your culture values is the recipe that I found works in handling these early to growth employee transitions.

And do you— I mean, when you say being transparent from day one, do you actually have the conversation with leaders kind of in early days and even now? And how does that conversation go?

Well, the leaders who have the humility, they understand. And you can have a conversation saying, hey, look, joining you for 4 years, and there is a reason why you have a 4-year vest. It's not 8 years, it's not 11 years, it's not 1 year, it's a 4-year. The 4 years is the time in which you can probably do your best work here, and hopefully you will be doing such a great job and scaling so well it will extend it. But statistically speaking, 4 years is 4 years. A majority, the fat middle of the distribution curve of employees, will reach their peak and then sunset with the company within that 4-year period. Now, there are a few things we can be doing together to extend the time, such as have great communication, great one-on-ones, work together. I would love to coach you, and I would love you to coach me. And I could— the list goes on. So let's be conscious about those, and let's work towards the best. But also keep in mind that there is the mechanics and laws of gravity. Mm-hmm.

And so being clear about that upfront, you feel like kind of cushions, you know, cushions the message because it actually is just true. Like, you know, you have to bring people in who've done it before because that's how you're going to get to scale.

Yeah.

Yeah. And at the same time, when you bring those people in, um, I've heard you say that one of your superpowers is that you hire people way out of your league. Is that true?

Yeah, I do manage to hire people out of my league.

How do you do that?

There's a book called Who? Yeah, that has a methodology for hiring people out of your league. And I'm very religious about that book. So literally everything the book says I do.

What are some examples for those of us who haven't read Who?

Continuously building the pipeline and just building relationships with such people, which goes back to building a network. Spending a lot more effort on defining the role you're looking to fill. The MOC process, the mission, outcomes, competencies.

I love that. That's so good.

And there is a whole chapter in the Who book on that. It's called the Who definition or whatever it is, the scorecard. Then having a very structured interview process. And there is very good behavioral interviews in the book. And so on and so on, allows you to just, A, punch above your weight on the network, to impress people with the quality of filtering you do, because the best candidates, when they encounter a very thoughtful and thorough interview process, realize that if this is how hard it is to get in, imagine the quality of people on the inside. And use this kind of process to scale it up. Like we arguably have one of the best teams in the Valley because we've been religious about who we bring on board.

And how do you teach or train other people? Because you know, of course, not hiring everybody. I mean, far from it. How do you sort of train that process and make sure everyone is activating and using that process in the same way?

Make the person who is most zealous, who is zealous about the whole process. You're head of recruiting and HR.

Is that what you did? Yes, yes.

But I mean, with the training, we instilled it. And also, almost every hire, I still kind of approve the, the recs. I go and double-check the, at random, different elements of the whole process. And if I have questions, I don't approve the hire until I get clarity.

Is there— can you think of— you don't have to say the name, but can you think of a recent hire that you had questions and you had to get more information? And what was— what were the kinds of questions you had?

Like, we have a minimum SLA on front door and back door references. Ah, when I don't see those, it's a big no-no. I look into what are the ratings from people on the panel whose judgment I trust based on a number of successful hires in the past. Mm-hmm. And if someone I really trust has given a thumbs down, that's a reason for me to go and dig in.

I see. I think it's really powerful to kind of keep up that kind of quality. Do you think about energizing candidates? I spoke to Paul English, the co-founder of Kayak. And he said that part of what he trained people for in terms of hiring— he's obsessed with hiring. And he's an aggressive hirer. And he's really proud of his quality. And he also is really proud of his like hit rate. When we decide we want you, you come because we focus on energizing you and recruiting you. Do you think about that also in terms of candidates you bring on?

Yeah, absolutely. I try to be low volume, high quality, kind of high hit rate type of recruiter. So yeah, I don't cast a wide net. And that process of defining who exactly you need in really high resolution allows you to be very judicious with the net you cast.

Yes. I also think it brings so much clarity to the team and to the candidate. Like that they really, I think that one of the things startups really get wrong is that they aren't clear what they're looking for. So then that creates a lot of churn in the process and then people get upset and then you sort of raise up this gap to sort of see like, oh, we don't quite know what we're, um, what we're looking for here. But it sounds like you really care. You really have solved for that.

Yeah, everything starts with figuring out what you need. The rest is easy.

I'm not sure if— have you experienced, you know, everyone's talking about the great resignation. Have you heard of it?

Yeah, I did. Uh, I don't think we've experienced that here.

Have you— how do you think your culture has maintained kind of stickiness of candidates? Of your employees?

I don't know. I mean, we're dealing with the second black swan event in 2 years, so definitely created some team cohesion and trust there. The culture stuck around. It definitely changed through remote world and all that stuff, but I don't think we've been hit by great resignation. And like, I actually don't think, I don't think at all. However, and now with macro tides changing, I don't think it's going to be accelerating moving forward because the world out there, even though the grass became a bit less green. And I think the Great Resignation is going to be a concept of the past year, I guess.

Interesting. So you think the pendulum is going to swing back to people staying with their companies?

I already— I'm already seeing it.

You're already seeing it, huh?

Yeah.

You know, one thing that I think a lot about when it relates to the Great Resignation is that, you know, if people— so like someone says, why'd you leave your job? And what they never say is, I had a great manager who cares about me, I had great opportunities to advance, but I felt like I enjoyed the people I worked with. Like, that is never what people people say when they say when they left. And I know that you are a big proponent of leadership yourself. And I feel like, you know, again, I heard in the podcast that you were talking about how part of your mission is helping to make the world better by improving leadership capacity, both with your product and probably also throughout your company. Can you talk more about that and why it's so important to you?

People don't quit their companies, they quit their leaders. For sure, or like they're off. And so most first-time leaders out there have no idea how to be a leader. Why? Because they never learned, they were never taught, they were never given leadership classes. They are typically lacking the basics. It took me many years of trial and error, and I'm not saying I'm the greatest leader ever, I'm hopefully better than I was before. And so that is actually the highest leverage point in pretty much every organization today, is the leverage that's hidden inside the leaders that could become better, that prevents employee churn, that accelerates employee performance, that leads to revenue growth. That's— that is having a strong frontline leadership team is probably the most unobvious but highest leverage advantage a company could have.

Yes, I'm a coach. I endorse this comment. How do you ensure that that is really, you know, aligned inside of People.ai, inside of your company?

You have to have a leadership development program. You have to define what it means to be a good leader. You have to provide your leaders— if you want your first lines to be good, the second lines have to be great leaders. You need to provide them with coaching opportunities, you need to provide them with clarity, and you need to remove obstacles from, from in front of them. Now it's all easier said than done. Yeah, but as you are thriving to, to build that company, just like paying attention to Do you like, do you respect, would you work for your frontline leaders? That's a simple question. Would you work for this person? If no, what the hell are you doing here? Why do you have them?

That's a very powerful question.

And I mean, our hiring methodology includes what we call ICED, stands for intelligence, character, coachability, curiosity, enterprise experience, domain knowledge. All of those except the last two are non-negotiable, and you have to have a yes on all. Is this person intelligent? Yes. If no, what are we doing here? Do they have a good character? Yes. If no, do you want to work with them? Are they coachable? Yes. If no, why would you want to have intelligent, good person that is just not coachable? Excellent. Are you curious? If yes, great. If not, it's gonna get really boring really quickly. So just having a framework there and running everybody, not just when they're joining, but continuously against this framework.

Yes.

Do I still think you're intelligent? Do I still think you're curious? Is the way to have better idea on that.

That's really powerful. Do you, in your one-on-ones, have those conversations? Like, are you still ICED? Or do you, in your performance appraisal process, also still have this notion of ICED inside of that, embedded inside of it?

That's a good idea for performance reviews. You're welcome. That's free. I'm continuously validating people on ICED.

Yeah, in your head.

Yeah.

And you feel your other— and your leaders are as well? That is something you guys talk about?

I hope so. I could be more intentional there.

Ah, okay. Well, you're not alone. You know, one thing you've also talked about, or I should say that has been said of you when you were named one of the top 10 CEOs by Comparably— congratulations on being named one of the top 10 CEOs— some of the comments were that you are radically transparent, radically transparent. So I'm curious, is that intentional that you are, that you want to be radically transparent? That's important for you as a person? What are your values?

It has its downsides, but I do believe in transparency. I do believe in— I just don't think you can scale the business without your team knowing which direction to row in. And not being transparent leads to mistrust. Mistrust leads to more cycle span and communication and figuring things out and so on and so on. So I just believe Opaqueness brings inefficiency.

Yes, totally agree. And I think transparency is— more transparency is better. But when you say it has its downsides, what's an example of like a downside?

Sometimes people are not ready to hear the truth. And when someone is not ready to a transparent method of communication, having access to more information than they should, they take it either at face value in terms of not understanding the full context, or even are not able to manage their reactions to it. Mm-hmm. And that's where more thrashing happens, right?

How do you then solve for that when that kind of thrashing happens?

It's extra work. You have to pre-educate people on what matters, why things are important, and how things are coming in. And give them the background needed to have to be able to consume the information correctly.

Ah, how do you pre— that's fascinating, pre-educate. I've never heard that before. Is that just sharing what's important and what the metrics are and what, how we do things around here? Is that what that means?

Yeah, and how to read things. And hey, you probably will see this, this result is surprising. Here is the bigger context about Yep, that makes a lot of sense.

You know, I again have listened to a lot of podcasts and read a lot about you, and I know that you have a lot of coaches yourself and mentors, and that you really pride yourself on being coachable. I'd love you to share how you personally prepare when you're gonna have a meeting with a mentor or a coach.

If it's the first meeting or a repeat meeting, my preparation is different. First meeting, I typically would spend an hour just researching everything there is about them. And it's YouTube, it's articles, it's whatnot, it's social media, and just try to understand them from the outside a little bit. I always prepare 5-10 questions I'm gonna ask you, and then I'm going with an open mind because, uh, the one thing that's common across all plans is it never goes to plan. But at least you'll show up thoughtful, you'll know the right level of detail, and you'll be able to say something that's relevant. For repeat meetings, it's— you always have an agenda and you always stick to the agenda. You execute. I find it's very disrespectful and people are not prepared for a meeting where they're taking your time and therefore I do not want to be doing that to others.

Got it. So preparation for you is key. And I'm sure they give you feedback. Have— is there a piece of feedback that you've gotten recently from a mentor or a coach that was very impactful for you?

The board management, a lot of it came from mentors and from observing others do it. In fact, recently I was invited to literally sit in on a board meeting of a CEO who was very proud of their own board dynamics. And it was very telling, very interesting. What I learned was the approach with which the founder structured the board and almost like the right to participate in the board meeting. And he demands from his board 3 things: inspire as the number 1 priority, brainstorm and help as the number 2, and only when you inspired the CEO and the team and brainstorm and help them with their current problems, only then you earn the right to inspect. And that was a very diff— different dynamic from what I've seen.

And how did that change your own style?

It's about to.

Watch this space. That's so great. You know, I can tell when you talk about curiosity, I can tell how much of a learner you are. I just really appreciate that you're kind of looking around and seeing how people can do it better and also open to coaching yourself and open to feedback yourself. You know, one thing as a founder CEO So, I don't know anyone in your company, but I do know this. There are people who don't want to tell you the truth because you're the boss, right? Because you're the founder CEO. So, what do you do? What techniques do you use to get people to tell you what's on their minds in light of that?

That's the one I'm still working on because top-down techniques do not work. You can build better systems for better inspection, which, sure. I think the best move is to create a safe space for people to share the hard truth and reward sharing things that are not pleasant to share. In fact, today I'm going to be doing that. I'm going for a happy hour with my team, and there's one thing that didn't go right.. And right before this podcast, I was in a meeting with them, and it was clear that they're very uncomfortable speaking about that thing. And the whole meeting was very uncomfortable with them because it was literally, uh, this thing didn't go right, go well, and all the way up to CEO is involved now. But my plan is to thank them for owning it and encourage them to continue owning it and position me as a resource and support for them, not as the main driver. There's another framework I really like. I learned from our CEO. It's called DACI. Stands for driver, approver, contributors, information only. And I think people get discouraged when DACI gets yanked from under them and reshuffled. You own this thing, you failed, therefore I'm the driver now. Versus what I think is really important is to reaffirm the roles and step up your support from a contributor's role, for example, but let them still drive it. Let them continue owning it. That's assuming you hired the right people.

Right. So letting them continue owning it, because I think people do get demoralized where something's taken away and they're not left to solve their own problems.

Exactly.

And then they feel like they've lost people's confidence. And then also, by the way, you miss the opportunity to train them. I'm glad you're gonna do that at your happy hour. And I, I do agree that it's actually so hard to get that real feedback and you have to kind of keep celebrating and keep asking for it, including asking for suggestions. You know, I'm curious, so many founders, uh, especially younger founders, which you are one, experience at times imposter syndrome or self-doubt. Have you ever experienced self-doubt, severe self-doubt, or imposter syndrome?

Like every day.

What's that like?

Tell me a founder who doesn't have imposter syndrome, and I'll tell you that they're not pushing the boundaries.

It's so true.

Oh, it's like, I mean, every day you're thinking, wow, am I even supposed to be doing this? Like, most recently, it's the whole Ukraine thing. Like, I was working on a number of projects that I'm like, Holy cow, I can't believe I'm even involved in this and the amount of leverage that I'm moving around. So yeah, I mean, imposter syndrome is partly annoying, but I also think it is the sign that you are growing and you are— it's like working out. Imposter syndrome is like the muscle ache. Means you worked hard and you pushed the boundaries and next day you're sore.

That's a great analogy. How do you handle it, or what advice do you have for founders to handle their own imposter syndrome?

What advice do I have for founders to handle their soreness?

Yeah, yeah.

At the gym. Push harder. Do it again.

Have you found your comfort zone? Have you found that you've expanded your comfort zone by pushing and keep pushing hard again?

Yeah. Yeah, for sure. I mean, like, imposter syndrome on its own, like, like being where you haven't been before, is kind of becoming a not natural state, but like a thing that is supposed to be happening.

So, Oleg, just a couple more questions. What do you wish you had known earlier on your journey?

Being very declarative about leadership principles. Or even more important, and this goes back to Andrei, how important culture values are. I initially was discounting them until I looked back and I realized that the company actually embodies culture values perfectly. It wasn't that we were hiring people to the culture values, the right people got attracted to these culture values.

So it sounds like what you're saying is paying more attention to them beforehand.

Or paying attention, be much more intentional and participatory in those in advance.

Yeah, yeah, that's really great.

Great.

And the last question is, what advice do you have for other founders as they embark on their own journey to grow into leaders?

That intentionality that I've spoken to multiple times is key. What I mean by that is Everything you do needs to have an intention behind it. And if you look at the success ratio of things that were done on a whim versus intentionally, you'll see a drastic, drastic difference. So writing down what are you going to do and why you're going to do it, and then following your thought from there, and what is important and how you're going to do it and with whom, etc., etc., etc. Is what allows you to declare your intention, at least to yourself. And a declared intentional action is much more likely to be correct action.

Amazing. Oleg, such a joy to have you. Thank you so much. This is going to be so valuable for so many people. I appreciate it.

Thank you, Alisa Cohn. Have a good one.

Thanks for listening to From Startup to Grownup. If you like what you heard, Give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.