Lead Through Contradictions,
Not Around Them

Helping overwhelmed tech leaders gain time, clarity, and agency

Directors and VPs I've worked with led teams at:

Amazon Google Ring Sonos Toast Harman Kardon

How We Work

The Frame

You come in with a problem (e.g., “My team isn’t aligned”). Instead of fixing it, we look at how you’ve framed it. What unexamined assumptions are you using to organize your reality? Usually, the problem isn’t the problem; the frame is what creates the problem and limits the possibilities

The Position

You are not operating in a vacuum. We map the “machine” you are in. How the organization needs you to be stuck right now. We distinguish between your personal traits and your structural position, relieving you of the guilt for systemic friction.

The Pattern

Why do you keep doing things that make you miserable? We look for the “hidden payoff,” the story you tell yourself that makes the suffering tolerable. We identify the fantasy that fuels your burnout so we can dismantle it.

The Signal

Your body knows the truth before your brain does. We look at where you feel the most resistance, anxiety, or exhaustion. We don’t try to soothe these symptoms; we use them as a compass to find the “Real” conflict.

The Shift

This is the pivot. You stop trying to “fix” the impossible tensions of your role (e.g., “Protect the team” vs. “Serve the Board”). You accept that these contradictions are not problems to be solved; they are the permanent terrain of the job. The shift happens when you stop seeking a false resolution and learn to act decisively within the tension.

Want to see if this approach is right for you?

Testimonials

Working with Keith has been life-changing to say the least. His active-listening skills and practical feedback/actions have yielded results that would have otherwise been impossible without him. I have learned everyday is a new opportunity to start over.

Laide Olambiwanu

CPO

Keith's coaching has been transformational and life-changing. I am always amazed at his ability to guide me to self-reflect on the blind spot, discover what's unsaid, and give attention to the root cause of the issue. It is not always easy to face your fears and doubts, and with Keith, I am not only challenged to do so in a supported environment, he can also give me concrete and actionable insights with his years of experience managing teams in tech companies.

Lucy Wang

Sr. Director PM

Keith is a thoughtful, thorough and compassionate mentor. He guided me through an impasse in my career and lead me to find own way through his considered approach to coaching. Keith’s strategies don’t feel like advice, they encouraged me to think deeply about myself and ultimately I found the path that was right for me. I would highly recommend working with him, and I will absolutely work with him again in the future.

Kristen Bender

SVP Digital Strategy

Over the past nine months Keith has helped me both as an advisor on organizational and performance matters, and with deep domain knowledge. He consistently surprises me with the wisdom of his ideas and how he weaves those thoughts naturally into our conversations.

David Kershaw

VP Engineering

I came in with a broad question that felt almost too vague to answer: What's my next professional chapter? Keith helped me break it down into something more manageable and asked the right questions to bring clarity. Throughout the sessions, I felt really supported and guided through each challenge that came up. I've learned to trust myself more — not just in my work, but in other areas of my life too.

Sherilyn Kamga

Cloud FinOps

Keith's great gift is the ability and insight to ask the right question at the key moment — often the question I've been avoiding asking myself — to help me move forward.

Kathleen Tibbetts

Director of Engineering

About Keith

With over 25 years of leading engineering, product, and business development teams in high-growth tech environments, I now coach Directors and VPs who are straining under the pressure of their roles, making countless decisions every day, and who need space to think, reset, and lead in a way that is both effective and true to what they want.
Most leadership advice oversimplifies what you face. You’re not just managing priorities, you’re navigating competing expectations, shifting systems, and the constant pressure to deliver while staying human.

What causes most leaders stress isn’t just the volume of work …it’s the strain of managing in two directions at once. You’re asked to deliver with fewer resources, adapt to shifting priorities, protect your team from turbulence, and still deliver on the expectations of those above you. That isn’t a communication gap. It’s the unseen emotional work of holding everything in place so others can keep moving.
My approach is not about forcing transformation or “fixing” you. It’s about slowing down just enough to see the patterns, assumptions, and trade-offs already shaping your leadership …and then making values-based decisions from a clearer perspective.

As an ICF ACC-Certified Coach, I blend my real-world experience with reflective, awareness-driven coaching.

Clients come to me when they want to:

Navigate complexity without being swallowed by it
Lead with grounded confidence while holding competing pressures
Build the conditions that allow teams to flourish
Make decisions aligned with values and context
Redefine success on terms that feel sustainable and self-honoring

Leadership will always involve pressure. The shift isn’t about escaping it; it’s about seeing where it comes from, deciding what actually deserves your energy, and leading with clarity instead of reaction.If you’re ready to lead from steadiness instead of strain, let’s talk.

Lead Through Contradictions, Not Around Them