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Strategic Thinking Support for Senior Engineering Leaders


Clarity in high‑stakes roles. Better decisions. Less isolation.

For Directors, Staff+ engineers, and technical leaders navigating complexity.
About

About Coach Jordan Larrigan

Coaching, to me, is like gardening. Growth takes time and care. Feeding what you need, pruning what doesn’t serve you, and watching you bloom into your full potential. I’ve been where you are: stressed, unsure, even isolated. I coach because no leader should have to feel alone.

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For over 20 years, I have led engineering teams at companies like Stash, Tagboard (as CTO), Myspace, and Medsphere. Now, I coach engineering leaders like you to achieve that aspiration, unlocking your full potential and accelerating your career journey.

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Leadership Calibration for Senior Technical Leaders

This is focused, structured thinking support for leaders operating in complex environments.


We work on real problems such as:
 

  • 🌱Organizational design and team structure

  • 💡 Promotion transitions and role expansion

  • 🤝 Executive presence and influence

  • 📚 Strategic tradeoffs and high‑stakes decisions

  • 🔒 Navigating conflict without burning political capital

  • ✅ Preventing burnout while increasing leverage

 

Leadership isn’t about having answers. It’s about thinking better.​

 

Apply for the Leadership Calibration Sprint
Or book a 30-minute clarity call to see if it’s a fit.

Service Tiers: Engineering Leadership Advisory

1

Leadership Support

2 Sessions per Month


For leaders who want steady calibration without heavy time commitment.
 

Includes:

  • Two 60-minute coaching sessions per month

  • Focused session agendas tied to current challenges

  • Clear action steps and decision frameworks

  • Light async support between sessions for quick clarifications

 

Ideal if you:

  • Want ongoing strategic alignment

  • Are navigating a specific challenge

  • Prefer space between sessions to implement
     

Investment: $300 / month

2

Leadership Acceleration

4 Sessions per Month
 

For leaders operating in high intensity environments who want tighter feedback loops and faster iteration.
 

Includes:

  • Four 60-minute coaching sessions per month

  • Deeper strategic work and structured leadership development

  • Decision mapping and organizational design walkthroughs

  • Priority async access for in-between session support
     

Ideal if you:

  • Are stepping into a larger scope role

  • Are leading through major change

  • Need consistent high-level thinking partnership

  • Want accelerated growth


Investment: $500 / month

Why Work With a Former CTO?

  • Zero Learning Curve: I’ve managed the budgets, built the teams, and reported to the Board. You don’t have to explain "technical debt" or "sprint velocity" to me.

  • Neuro-Inclusive Coaching: As an ADHD coach, I specialize in helping leaders build systems that work with their brains, not against them.

  • Outcome-Obsessed: We focus on the metrics that matter: retention, delivery speed, and your personal peace of mind.

"I was already a Senior Engineer and acting as a tech lead, but I wanted to become a more effective leader for my team and prepare myself for future management opportunities. Jordan's coaching was exactly what I needed. He provided pragmatic guidance on everything from improving team communication to navigating challenging technical disagreements. His experience as a CTO was invaluable, he's been there and understands the real-world pressures we face as engineering leaders. Because of his coaching, I'm now a stronger and more confident lead engineer, better able to guide my team and contribute to the broader engineering organization. I highly recommend Jordan to any senior engineer looking to enhance their technical leadership and overall leadership skills."

Cole F, Lead Engineer, [Boeing]

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