D2 Product Preview: Building an AI Coach for Eng Managers — A Non-Technical Founder's Journey

For the last decade, I've worked with engineering leaders on a problem that keeps getting worse: helping their teams grow. Not just skill up—actually grow as people through their work. I got obsessed with this because it changed my life: realizing personal and professional growth aren't separate things.

We had some success, but kept hitting the same wall: managers would learn new coaching approaches, get excited, then get buried. Sprint planning, incidents, roadmap pressure. Within weeks, people development was back on the back burner. The urgent always beat out the important.

Then the last few years made it worse. Remote work, higher stress, more isolation—and somehow managers are expected to get more from people while having less time to actually develop them.

Why I'm Building This (as a non-technical founder):

In 2023, I realized AI might finally make it possible to put a tool in managers' hands in the moment—not another dashboard to check, but something that actually helps them coach better without adding work.

The Hard Technical Problems We're Solving:

1. Making AI that challenges, not just answers: Getting the AI to push managers to think deeper (not just give them scripts) has been brutally hard
2. Data without surveillance: We're figuring out how to pull useful context—Slack, meetings, PRs—without becoming a monitoring tool. "Ren is not a narc" is our design principle
3. Zero friction: If it takes more than 10 seconds or requires leaving their workflow, managers won't use it

What's Working So Far:

1. We're clearly solving a real problem—validation has been strong
2. The AI finally works well enough to be useful (took longer than expected)
3. Early users are actually changing how they manage, not just collecting insights

What I'm Still Wrestling With:

1. How much automation is helpful vs. making leadership feel mechanical?
2. Getting the data integration right without creeping into surveillance territory
3. Building AI that helps managers be more human, not less

This is a conversation about building AI tools for the messiest part of engineering leadership, the human part. Happy to dig into technical architecture, product decisions, or just the weird experience of being a non-technical founder building AI tooling for devs.