Coaching for engineering leaders

You’re running an AI rollout. The metrics are mostly green. Your team has stopped pushing back. Something feels off - and you can’t tell whether it’s alignment, friction, or the start of attrition you won’t see until it’s too late.

That’s the conversation this coaching exists for.

Who this is for

  • Engineering managers, directors, and VPs at 50-500 person tech companies
  • Running an active AI tooling rollout, or about to run one
  • Privately uncertain whether your team is bought in or quietly compliant
  • Seeing no ROI from AI rollouts while engineers’ morale is slumping.
  • Looking for someone who’s navigated this kind of org-level tooling shift before - and isn’t going to sell you a framework PDF

This is not the right work for: pure individual coaching unrelated to a team context, generic leadership development without a tooling-transformation lens, or anyone looking for a vendor to validate an AI strategy that’s already locked in.

What an engagement looks like

A typical engagement runs 12 weeks:

  • Weekly 1:1s - 60 minutes, focused on what’s actually happening on your team this week, not abstract leadership theory.
  • Async support between sessions - short-form Slack or email, for the in-the-moment decisions where a 24-hour wait kills the value.
  • Targeted diagnostics - frameworks like the 12 Signals checklist you can run on your team in under an hour, with a debrief in the next session.
  • Stakeholder navigation - how to manage upward (the CTO asking for adoption metrics) and across (peer VPs, the AI champion you appointed) as the rollout matures.

Pricing is structured per-engagement, not per-session. The first conversation is a 30-minute discovery call at no cost - we both decide if the fit is real before any commitment.

How to start

Three doors in:

  1. Take the diagnostic first. 12 Signals Your Team Is Performing AI Adoption, Not Aligning To It - a 25-minute self-assessment that’s the same starting place a paid engagement begins with. Run it on your own team, then decide if the coaching conversation is worth having.
  2. Book a discovery call. 30 minutes, no agenda beyond your specific situation. I’ll ask what’s happening, you’ll ask what working together would look like. No pitch.
  3. Email me. anton@otomato.io. Tell me what’s going on. I read everything.

Anton Weiss is a former CTO and longtime DevOps transformation consultant who now coaches engineering leaders through cultural inflection points. More about Anton.