Featuring: Jerry Lee (Chief Operations Officer), Cadogan Price (Head of Revenue), and Daniel Cho (Head of Product Engineering)

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Introduction: Leadership Is An Evolving Practice

Leadership rarely follows a straight line. There is no formula to memorize or checklist to complete. It is an ongoing practice shaped by the moments you get right, the ones you get wrong, and all the judgment calls in between. 

At Wonsulting, building a mission-driven company has required each of us to lead through uncertainty, balance analysis with instinct, and create an environment where we all feel bold enough to try.

This edition of our Leadership Lessons series started as a simple chat among our exec team. But somewhere between the laughs, the stories, and the “remember when…?” moments, we found the secret behind rapid innovation:

True leadership has nothing to do with managing outcomes. It is all about engineering an environment where progress can actually happen.

Let's unveil the full story.

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1. What’s the most important leadership lesson you’ve learned while growing a mission-driven company?

Jerry

One of the biggest lessons I’ve learned is the importance of having the right co-founder. A person who complements your skills AND challenges the way you see the world.

Early on, I approached leadership the way Google trained me: know every angle, question every assumption, and mitigate every risk before taking a step. 

Jonathan came from a completely different background. He’s wired for action. He learns by doing and iterating quickly. So, naturally, we clashed. I still remember one moment clearly. We were debating a major decision, and I pushed hard on the risks. 

Jonathan paused and said, “Jerry, you know we’re on the same team, right?” It was a profound question that led to introspection. I realized leadership isn’t about being the one with the right answers. It's about trusting the person beside you, even when their style is different.

Since then, I’ve learned that building a company isn't always a debate between analysis and action. There are times to pause and times to move. Jonathan makes me faster. I make him more deliberate. That balance is one of the biggest reasons Wonsulting is where it is today. 

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Cadogan 

For me, the biggest leadership lesson is this: there is no playbook. The best leaders don’t stop at managing; they orchestrate. They understand that strategy without execution is empty, and execution without meaning is directionless.

Leadership happens at the intersection of intuition and intelligence. Some leaders lean heavily on data; others lean on creativity. Outstanding leaders know how to do both. That's why they build environments where ideas can flourish and then turn those ideas into movement.

Launching our 120-Day Performance Guarantee was one of those moments. It was bold. It was risky. There was no playbook for guaranteeing job outcomes in an unpredictable industry. 

Internally, there was hesitation. Some worried it was too risky, others that it would create unrealistic expectations. But we decided to move forward anyway because it aligned with our mission.

What made that launch successful wasn't really the idea. It was how the team executed under uncertainty. We balanced instinct with data, stayed curious when early feedback was mixed, and adjusted in real time. Leading through that uncertainty taught me something I’ll never forget: leadership isn’t about protecting perfection, it’s about protecting momentum.

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Daniel

I’ve come to believe that leadership is overwhelmingly an art, not a science. You can have all the data, all the frameworks, all the best practices. But unless you know how to apply them at the moment, they won’t get you very far.

People think “swinging big” means going all-in. If you ask me today, you're swinging big when you pilot a lightweight version of a big idea. Or you do something extraordinary that balances creativity with the resources you have today.

One other lesson I've learned is this: Just because you have to change your approach later doesn’t mean your earlier approach was wrong. It just means circumstances have changed. Understanding when to pivot is the art.

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2. How do you balance data, instinct, and timing when making big decisions?

Jerry

Decision-making for me has always been a balance between rigorous analysis and decisive action. My instinct is to scrutinize every angle. And that comes from years at Google where every detail mattered. But leading a fast-moving company has taught me that sometimes the best data comes after you start moving.

Over time, I’ve learned to identify when a situation calls for deep thinking vs when it calls for momentum. Leadership is knowing which gear to use.

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Cadogan

A big part of leadership is learning how to read the undercurrents. The crumbs are always there, just don't overlook them like everyone does. This reminds me of a particular event while I was at DemandVenture.

When we expanded DemandCapture’s GTM strategy into EMEA, there were no loud trends. We just started following some small and subtle patterns, like the unexpected inbound interest, different engagement behaviors, and cultural nuances in how buyers responded.

Without leaving anything to guesswork, we ran small tests. We tried localized messaging, adjusted pricing, and relationship-first outreach. Those early, instinct-driven tests eventually led to three new Fortune 1000 clients and $225K in revenue.

For me, instinct and data aren’t opposites. They inform each other.

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Daniel

When I'm making a big decision under pressure, I think about constraints differently than most people. I ask myself: Is this a resourcing issue or a scope/understanding issue? A resource issue is something that more help or hiring could solve.  A scope issue means I don't yet understand what I'm actually dealing with. 

Distinguishing early is important because they require completely different solutions. If I misdiagnose the constraint, I either throw resources at the wrong problem or waste time analyzing something that just needs execution. For me, data and instinct work best when you're clear about what you're actually solving for.

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3. How do you build and protect a culture where people feel safe taking risks?

Jerry

For me, culture starts with trust and alignment. My partnership with Jonathan taught me that different styles are not threats. When people know you’re on the same team, they’re more willing to take chances, challenge ideas, and move fast without fear of being judged.

That's the culture I try to build: one where people feel safe taking risks and pushing boundaries, and where questions feel collaborative instead of confrontational.

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Cadogan

I’ve seen firsthand how fragile culture can be. There was a time when ideas struggled to get off the ground unless they came with a spreadsheet to “prove” them. That mentality slowly chipped away at creativity.

But that has shifted. People have started taking initiative again. We are testing, learning, and sharing. And it reminded me of something I heard at a leadership summit: The best thing you can do as a leader is celebrate when someone takes a chance.

That’s been my north star ever since. One harsh reaction can send people into hiding for months. One encouraging response can unlock innovation for years.

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Daniel

I believe psychological safety grows from ownership. You don’t need to lead a big team to be a leader. If you can own a project, iterate after failures, and think creatively when things get messy, you’re already practicing leadership.

Culture thrives when people feel like they can try, miss, adjust, and try again, without fear of being punished for learning.

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4. What role does failure play in leadership growth?

Jerry

Failure gets easier to navigate when you stop viewing decisions as competition and start viewing them as collaboration. When someone on the team makes a call I wouldn’t have made, my question isn’t “Why did you do that?” It’s “What did we learn, and how do we get this right together?”

Because if they're thinking differently, they might be seeing something I missed. People take risks when they know disagreement won't be punished. They push boundaries when they trust that we really are on the same team.

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Cadogan

Every major initiative I’ve led has had moments where things got messy or uncertain. During the Performance Guarantee rollout, we were under pressure, the feedback was mixed, and it would’ve been easy to panic. But staying calm, curious, and focused allowed us to learn our way into a breakthrough.

Failure isn’t the problem. The way leadership responds to it is what defines the culture.

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Daniel

Most “heroic leadership moments” don’t happen after one try. They happen after multiple failed attempts. When something doesn’t go as planned, I ask myself one thing:

“Did I have the information I needed at the time to make a better decision?”

If the answer is yes, I learn and adjust.
If the answer is no, I give myself grace because I made the best call I could with what I knew. Either way, the outcome is growth.

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5. How do you lead when circumstances change quickly?

Jerry

I think of leadership as a balance of gears. Jonathan helps me move faster when I’m overthinking. I help him slow down when something needs deeper analysis. That complementary rhythm keeps us adaptable without being reactive.

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Daniel

I see change  as a natural order of life. Approaches that worked six months ago may not work today, and that’s okay. Leadership is recognizing when it’s time to evolve and doing so without ego.

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Leadership, In Their Own Words

A deeper look at each leader’s personal philosophy

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Jerry

“Different leadership styles are complementary engines.”

My biggest leadership growth came from understanding that someone who leads differently isn't blocking you—they're balancing you. Once I embraced that, collaboration became easier and decision-making became clearer.

For me, great leadership comes from trusting complementary strengths, slowing each other down when necessary and speeding each other up when it matters most.

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Cadogan

“Protect momentum over perfection.”

I’ve learned that culture is fragile and leadership shapes it more than anything else. One reaction, good or bad, can alter whether people bring forward their best ideas or hide them.

For me, leadership isn’t about controlling outcomes. It’s about creating the conditions where great ideas can happen and move.

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Daniel

“Leadership is an art, not a science.”

My philosophy is simple: stay adaptable. The approaches that worked yesterday served their purpose, but today might require something different. I’ve learned the leaders who grow are the ones willing to iterate, not just on their work, but on themselves.

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Conclusion

Across operations, revenue, and engineering, a shared belief emerges:
The focus of Leadership at Wonsulting is to create an environment where people can think boldly, act courageously, and move missions forward.

It requires intuition, intelligence, partnership, trust, and a willingness to evolve. But above all, it requires leaders who protect momentum, because momentum is what allows impact to scale.

That’s how you build a mission.
That’s how people grow.
And that’s how Wonsulting continues helping millions worldwide.