Coaching for product, design, and tech leaders who know something has to change
When success feels empty, it's not you, it's your approach
Your team's crushing it.
You've guided teams through evolving delivery models, shifting priorities, and constant change.
So why does it still feel like you’re performing leadership instead of living it?
Most leadership advice? It's surface-level fixes, all safe questions and overused frameworks. What I do is different. We dig into the stuff you don't even realize you're assuming and the beliefs you’ve inherited. Boxes you've put yourself in without knowing it. Because often the real problem isn't what you think it is.
my unique approach
Real experience, asking deep questions, with zero tolerance for surface-level solutions
What makes my coaching for product and design leaders different:
Industry-specific guidance from someone who understands creative field complexities
Unique approach that works around you, not rigid lesson plans
Focus on you as a person, not just your professional performance
Tools that range from evidence-based frameworks to expanded states of consciousness
Research-informed methods (my PhD in Organizational Development & Change)
Client Love ♥
“Jacob is really good at helping me see the boxes I've placed myself in and challenging those boxes.”
— Lindsay M, UX Leader
1:1 coaching for product, design, and tech leaders
This isn't checkbox coaching. It's for leaders actively rethinking how they show up.
The process
25-minute intro call to explore fit and potential growth areas
45-minute foundational session to define what success looks like for you
Weekly or bi-weekly 45-minute sessions over 2-3 months (can extend if beneficial, but I aim to keep our focus sharp)
The tools
Tools like Leadership Circle Profile and Neething Brain Instrument to understand your thinking preferences
For those curious, we can also explore psychedelic integration—no pressure, just a deeper tool if it fits your journey.
Values exploration and integration into your daily leadership habits
we’ll work on
① What’s Up
We start with what’s alive for you right now – big goals, pressing changes, or the quiet misalignments you can’t ignore anymore.
② What Matters
We dig into values and motivations underneath the surface. This isn't just strategic, it’s emotional, physical, and human.
③ What’s Next
Together, we define what needs to shift. That might involve new habits, leadership moves, or a deeper reckoning. It’s unique to you.
Ideal for: Leaders feeling disconnected despite outward success, navigating career transitions, or questioning their next chapter. You're introspective, curious, and looking for deeper solutions.
Client Love ♥
“It’s not just career advice. Jacob understands the creative identity crisis and gets what it means to be a creative leader at a crossroads.”
— Helen L, Lightspeed Commerce
Team coaching and offsites that don’t suck
Ideal for leadership teams facing rapid scaling, post-org realignment, or integrating AI tools into cross-functional pods. Get your team out of the weeds.
What we create together
We begin with a discovery call to understand your team dynamics, current challenges, and goals. Every team engagement is different, but typically includes some combination of:
Strategic alignment sessions that cut through the noise and focus on what matters
Trust-building work that goes deeper than personality assessments
Decision-making frameworks for teams navigating AI integration and rapid change
Leadership team offsites designed around your specific challenges, not generic templates
Example activities
Team charters
Purpose statements
OKRs
Goal setting
Roadmaps with prioritization
Strategic planning frameworks
Role clarification exercises
how it works
① Planning
We identify your team's specific dynamics and design activities that address real challenges, not theoretical ones.
② Facilitation
I handle the group dynamics so you can participate fully instead of managing the room.
③ Follow Up
Post-session coaching to ensure insights translate into sustainable team practices that last beyond the offsite experience.
Ideal for: Leadership teams feeling misaligned, organizations integrating AI tools, or groups that have outgrown their current operating rhythms.
Working with AI as your newest team member?
Your team isn't resisting AI—they're trying to stay relevant. I help you navigate:
Building trust when roles are shifting
Integrating AI tools without losing human creativity
Leading through the anxiety of automation
Creating new workflows that enhance rather than replace
Maintaining team cohesion during tech disruption
This isn't about AI training. It's about leading humans through technological change.
Frequently Asked questions
Your burning questions (and a few you didn't know you had)
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Both. I've been doing this long enough to know that good coaching happens wherever people feel comfortable. Most of my 1:1 work is virtual anyway - easier for everyone. Team stuff? I can facilitate remotely or be in the room. Whatever works.
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Hell yes. Most executive coaches have never had to explain to a CEO why the design system is broken while three engineers are breathing down your neck about technical debt. They've never sat in a room where "user research says one thing, stakeholders want another, and the timeline is impossible" is just Tuesday. I've lived this stuff. That's the difference.
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Nope. Look, it's one tool in the toolkit—a pretty powerful one—but most people aren't ready for that conversation on day one. And that's fine. We start where you're comfortable and go from there.
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I'm currently researching Human-AI teams for my PhD in Organizational Development & Change. Combined with 20+ years leading tech teams, I understand both the technical possibilities and the human anxieties.
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We talk. For 25 minutes. Just two humans figuring out if this makes sense. I'll ask you some uncomfortable questions. You'll probably realize there's more to unpack than you thought. That's normal—and exactly why we're talking.
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Individual coaching typically begins with a 2-3 month engagement. Team coaching is custom-priced to meet your specific needs. We'll discuss specifics during our discovery call, no surprises or pressure.
Frequently Asked questions
Your burning questions (and a few you didn't know you had)
-
Both. I've been doing this long enough to know that good coaching happens wherever people feel comfortable. Most of my 1:1 work is virtual anyway - easier for everyone. Team stuff? I can facilitate remotely or be in the room. Whatever works.
-
Hell yes. Most executive coaches have never had to explain to a CEO why the design system is broken while three engineers are breathing down your neck about technical debt. They've never sat in a room where "user research says one thing, stakeholders want another, and the timeline is impossible" is just Tuesday. I've lived this stuff. That's the difference.
-
Nope. Look, it's one tool in the toolkit—a pretty powerful one—but most people aren't ready for that conversation on day one. And that's fine. We start where you're comfortable and go from there.
-
I'm currently researching Human-AI teams for my PhD in Organizational Development & Change. Combined with 20+ years leading tech teams, I understand both the technical possibilities and the human anxieties.
-
We talk. For 25 minutes. Just two humans figuring out if this makes sense. I'll ask you some uncomfortable questions. You'll probably realize there's more to unpack than you thought. That's normal—and exactly why we're talking.
-
Individual coaching typically begins with a 2-3 month engagement. Team coaching is custom-priced to meet your specific needs. We'll discuss specifics during our discovery call, no surprises or pressure.
You CAN be yourself and still succeed
Lead without the corporate cosplay