The Hagakure #87: One Year In

Signals, systems, and staying human.

Photo by Nick Fewings on Unsplash

One year ago, I stepped into the role of CTO at Resquared, with responsibility for both product and engineering. I walked into a startup with traction, a product in market, and a team already sprinting.

There was so much that was already working: a product customers were paying for, a team that had weathered tough moments, and founders who had gotten the company off the ground through sheer grit. Getting to that point was no small feat—many early-stage startups operate in exactly this way, and for good reason. None of that should be taken for granted.

And yet, what I found under the hood showed just how much opportunity there still was to grow and evolve.

What I Found

There wasn’t yet structured product or engineering leadership. No shared sense of how work got prioritized, planned, delivered. Engineering was mostly reactive. Product was a backlog. Discovery and delivery were disconnected. Nobody owned the full picture.

There was also a profound disconnect between product & engineering and the rest of the company—especially customer success. Not just misalignment, but friction. CS felt unheard and unarmed. Engineers felt overloaded and misunderstood. Feedback flowed erratically, often too late and too hot.

And like many early-stage startups, Resquared was still entirely founder-led. No management layer. No structure for delegation or distributed decision-making. Strategy and fire drills all flowed through the same few people. That approach had worked for the stage the company was in—but it was also beginning to limit our ability to scale.

What I Managed to Do Well

People First

I made a few tough calls. Let go of some. Brought in others.

Not because they were bad people or lacked skill. But because over time—and after multiple rounds of feedback—it became clear that the system I was building and profoundly believed in wasn’t one where they would thrive.

The people who joined? Curious. Humble. Clear thinkers. Fast learners—which I love and consider non-negotiable. Willing to challenge assumptions. Willing to say "I don’t know." They helped chang our dynamics for the better.

Building a Cohesive System

My goal was to build a connected system for product discovery and delivery that the whole team could shape, understand, and trust. I applied all my systems thinking tools to help me do this.

Once you see it, you can’t unsee it.

We landed on the Atlassian suite:

• Jira Service Management for internal helpdesk

• Jira Product Discovery for capturing and refining ideas

• Jira Software for project planning and delivery

The tools weren’t the point. The system was.

We set up bi-weekly pulses—Mondays to align, Fridays to reflect. People raised issues early and asynchronously. Decisions became traceable. Priorities clearer. Ownership distributed.

It wasn’t process for process’s sake. It was rhythm. And over time, it became second nature. Because the team helped build it, they owned it.

The result? A radical improvement in velocity, predictability, and consistency. The product itself still has a long way to go, but the system that can build a great product is largely there—and it’s continuously getting better. The product is, after all, a lagging indicator of the quality of the socio-technical system that produces it.

Staying Human

I stayed human. Present. Honest. No persona. No performance. Just there.

I’ve always believed in showing up as part of the team, not above it. What you see is what you get. And once again, that was confirmed to be the right approach—especially when things get hard.

Mistakes

Deliverability

Email deliverability is core to our product. It’s how our customers reach their customers.

And I missed it.

I had never worked on a product where deliverability was central. I didn’t know what great looked like. And I assumed things were probably fine.

They weren’t. The moment it clicked—after conversations with people outside the company who were deep in the cold email deliverability world—I knew we had a problem. And we had to move.

We did. Fast. We prioritized it. We made big changes. And I counted on excellent engineering work—and excellent engineering leadership from my most senior engineer—to fix it.

Lesson learned: when something is core to your value prop, don’t assume. Validate. Pressure test. Own it. Be a little paranoid.

The AI-Native Shift

We’re in the middle of an industry-wide paradigm shift. Since the transformer paper—and especially since ChatGPT’s launch in late 2022—we’ve been living through a moment as big as the iPhone, the web, or social media.

And I was slow to fully embrace that.

We adopted AI features early. But I didn’t grasp quickly enough that being truly AI-native requires rethinking product architecture, user expectations, even team structure.

It’s not too late, and we’re moving fast now. But the cost of being slow on posture is real.

Next time I find myself in a paradigm shift of this magnitude—if ever—hopefully I won’t hesitate.

Challenging Assumptions (Outside My Team)

Inside my team, I did well here. There’s trust, psychological safety, and shared language. I can raise challenges and spark hard conversations without derailing relationships.

But when it came to the company’s deeper assumptions—especially in a founder-led environment—I often struggled. I underestimated how much timing, tone, and context matter when challenging deeply held assumptions. Too fast, and it can land like an attack. Too blunt, and it may create resistance. When that happens, momentum dies.

This is one of the hardest parts of leading inside a founder-led startup. You have to help reshape the system while preserving the trust of those who built it. That takes more finesse than I had at times.

Source: The Systems Thinker

What Helped Me

• Systems thinking. Everything I did to reshape product and engineering was grounded in this. I see loops, not lines. Dynamics, not snapshots. It helps me avoid shallow diagnosis and think in second- and third-order effects.

• A coaching background. I try to ask better questions. I try to meet people where they are and help them grow. I’m not always successful—but that’s always the intent.

• Clarity and honesty. Creating clarity without rigidity. Developing competence instead of rescuing. Saying the uncomfortable thing, transparently, when it matters.

• Covey’s golden rule. Seek first to understand, then to be understood. The most important of his principles, in my view. When I live it, it changes everything.

• A sharper relationship with data. I’ve become more incisive in defining what to track, what gives signal, and what’s noise. I decide more from what we know—not what we wish were true.

What I Don’t Have Yet

• The ability to drive change from systems thinking without resistance. Seeing early isn’t enough. I’ve learned how especially challenging it can be to translate a systems view to people who tend to operate from a linear, task-focused mental model rather than seeing the broader dynamics and interdependencies. You have to pace it. Shape it. And most of all, create a context where others want to join you in solving it.

• The courage to focus harder. Real focus should hurt. I’ve often avoided that pain—chasing too many threads, saying yes too much even to—especially to—my own ideas. That creates pressure and noise. I’m learning to cut deeper.

• A true outcome-first reflex. I still default too easily to outputs and task mode. But I’m honing my intuition. More and more, the first question I ask is, "What outcome are we trying to create?" I'm not fully there yet—but the shift is underway.

What I Don’t Know I Don’t Have Yet

I don’t know what I’m still blind to. More than anything, I hope others will tell me. Which is harder the more senior you get. The feedback gets filtered. The air gets thin. It’s lonely sometimes.

But that’s the job.

And None of This Alone

Absolutely none of what I’ve done this year would’ve been possible without the people around me.

I’ve learned more about analytics from my PM than I could hope for. I’ve learned tremendously about principled engineering from my lead. The list goes on. I've literally learned something, no matter how small it may have been, from everyone who walked alongside me on this journey. Cheesy to say, true nonetheless.

Over to You

If any of this resonated—if you’re wrestling with similar tensions—I’d love to hear from you:

Is there a part you’d like to see unpacked more deeply? Curious how leadership, systems, or decision-making evolve inside a startup like this?

Let me know.