Trust, AI and Great Sales Leadership: An Interview with Mark Kosoglow

I recently sat down with Mark Kosoglow, CRO at Docebo, to talk about AI, sales leadership, and how he's thinking about building high-performing teams.

Mark had great observations about how quickly the landscape is changing. He described one group of people who are experimenting with AI a little at a time, and another group that's already building workflows and capabilities that feel years ahead of everyone else.

It's an interesting way to think about where we're headed. But as our conversation continued, I realized that, when we talk about AI, we’re often actually talking about leadership. The companies that are successfully adapting to the AI world are doing so on a solid foundation of trust. 

I’ll recap the highlights of our conversation in this article, or you can watch the entire interview here. 

Great Coaching Starts With Great Relationships

One of the things I've always admired about Mark is the teams he's built. When he started talking about building culture during his time at Outreach, I was surprised to hear the approach he took. Rather than talking about process, compensation, or hiring, he talked about trust. Mark subscribes to the philosophy that if people genuinely believe you care about their success, they’re often willing to try things they otherwise wouldn’t. 

The benefits of investing in trust among your people compound over time. They’re more likely to feel comfortable taking risks, they’re more engaged, and they’re more invested in the success of the team and the business. 

Eventually, a culture like that starts reinforcing itself, and you find yourself with a real, unified team. 

AI Can Identify Problems, But Managers Still Have to Solve Them.

Mark made the salient point that managers often get blamed when people leave organizations. His perspective is that the reality is often way more nuanced. 

Many reps simply don't know how to articulate where they're struggling, leaving managers to guess (and often, to guess wrong). The result is that trust begins to erode and the relationship eventually breaks down. 

Mark sees an opportunity here—not for AI to replace coaching, but for it to give managers better information they can use to strengthen their team. 

Instead of discovering after the quarter that someone struggles with negotiation, pricing, or qualification, AI can help managers spot patterns much earlier and coach with far more precision.

Not Every Great Seller Should Become a Manager

I also appreciated Mark's honesty about career progression. In sales, we've created an assumption that the next step after becoming a top-performing rep is becoming a manager. Mark challenged that idea, and I think he’s got a great point. 

He shared the story of one of the best account executives he'd ever worked with—a seller who consistently generated incredible results, loved coaching teammates informally, and had absolutely no interest in becoming a manager.

He was motivated by freedom, not management. It was a good reminder that leadership isn't the only successful career path. Sometimes the best thing an organization can do is help exceptional sellers keep selling.

Culture Doesn't Happen by Accident

Toward the end of our conversation, Mark described a program he runs with top performers inside his organization. Every quarter, he brings together a small group of high-performing employees to talk candidly about what's working, what isn't, and what leadership may be missing. He takes their feedback very seriously, often acting to make changes before the meeting is even over. 

I like this program itself, but I especially like the philosophy behind it. Mark believes the people closest to customers often have the clearest view of what's happening inside the business. The challenge is creating an environment where they feel comfortable saying it, which requires a level of trust that many sales environments don’t have. 

Process Makes Great Leadership Scalable

The last thing that stood out to me was Mark's answer when I asked where he starts after joining a new organization. He didn’t hesitate—he starts with process. That’s where consistency begins, and consistency creates visibility, which allows leaders to coach more effectively. 

Interestingly, some of his most valuable processes aren't operational at all. Rather, they’re leadership habits like regular conversations with top performers, offering reps open access to executives, and creating intentional feedback loops. 

I came away thinking that AI is going to make great managers even more effective, but it won’t replace the foundation of trust that great leadership has and always will require. 

I’m grateful to Mark for the time. Check out our full conversation here.

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