Making the Leap: Why I’m Coaching Myself with AI

New here? I recommend checking out my first entry to understand the 'why' behind these reflections before you dive into the details.

This week, I started my new role as the Strategic Partnerships Director at ActiveCampaign.

For a long time (a 13 years history can be found in my Linkedin profile), I operated as an independent contributer. Making the jump to a Director-level position is a major shift, and—if I’m being honest—it brought a healthy dose of impostor syndrome with it. I realized that there is an entire niche market of talented people ready to make this same transition, but there is no roadmap for it.

So, I decided to build one.

The "Needle in a Haystack"

Most people are too focused on the title to capture the transition as it happens. It is a "needle in a haystack" moment—a rare chance to see how a leadership narrative is born in real-time. I’ve decided to make this level of reflection my competitive advantage. I am using these first few weeks not just to perform, but to study my own performance..

The AI-Powered Narrative

I’m not a professional author, but I am a strategist.

For my first five days on the job, I’ve been using ChatGPT as my executive career coach. Each day, I ask it to drill down into my actions, inactions, and strategy. By leveraging tools like Wispr Flow for voice-to-text to explain my learning moments, I am crafting my story, my learnings, and my failures with the freshest perspective.

My goals:

Navigate the IC-to-Director transition with self-reflection.
Understand the "how" of cross-functional leadership through building scalable systems.
Execute a strategy to help internalizing the "learnings" through the outcomes of my work.
Living a growth mindset that unlocks everything.

The Logistics Life with two kids means my writing time is precious.

I’ll be publishing a weekly recap every Sunday. My first week recap is live!

Welcome to the journey.

Week Four: Alignment as an Operating System

Week 4 reinforced a core leadership realization: Cross-functional alignment is not a side task—it is the work. TLDR: Leadership at this level is less about controlling outcomes and more about creating the conditions for teams to move together with clarity, trust, and shared purpose. I’m increasingly operating as

Week Three: Cross-Functional Alignment is the Real Work

Leadership at scale is not about having the best individual idea. It is about creating systems where people align, trust each other, communicate clearly, and execute together. Week 3 was about moving from: high-performing strategic contributor to organizational orchestrator. * Defended positions under pressure * Built alignment frameworks * Shaped strategic narratives * Strengthened

Week Two: Leadership At Scale Is About Leverage, Not Output

Yes, I’m late with my Week 2 post. It was Mother’s Day weekend, and I had a fantastic weekend. For three straight days, I enjoyed family and friend time around the pool in the not-hot-enough Las Vegas weather. Moving forward, I will summarize the week with an AI-generated

Week One: Learning the System Before Scaling the Vision

4/27/26 - 5/1/26 New here? I recommend checking out my first entry to understand the 'why' behind these reflections before you dive into the details. TL;DR: From Participant to Architect If I had to define my first week in one phrase: Learn the