Working with CD usually begins with curiosity. Many people find their way here after a page on this site sparks a question about their own team, company, or life. If a conversation feels worthwhile, CD coaches leaders, advises companies, speaks at events, and collaborates on writing. Every engagement starts the same way: listening first, to understand what matters most and why. From there, the work is shaped together. Some engagements last a single conversation. Others grow into longer partnerships.
The pages on TalentWhisperers.com remain free for everyone. This page simply explains how we might work together if you would like to go further.
CD as a Coach
Helping leaders and teams turn obstacles into growth.
A Rare Combination
Few coaches have themselves been through and led companies through the existential crises their clients face. Fewer operators have trained as coaches. CD brings three perspectives together. As an operator, he has helped eleven disruptive software companies through existential crises. Seven became unicorns, an outcome venture capitalists commonly put at about 1 in 100 funded startups. As a coach, he completed Co-Active coaching training and has coached founders and executives since 2017. As a teacher and athletic coach, he taught K-8 and coached players and teams to winning national championships. None of it was a solo journey, and the teams deserve the credit. What CD offers is the pattern recognition that comes from living all three.
Background at a Glance
- Helped eleven disruptive software companies through existential crises. Seven became unicorns, together exceeding $400 billion in peak valuation. The full story.
- Roles ranged from architect of the world’s first integrated software development environment to VP Engineering at BroadVision, internal startup lead for QuickBooks Online at Intuit, head of Yahoo! Games engineering, EVP Engineering at Twitch, and VPE and CTO at Prosper.
- Coaching and advising founders and executives since 2017.
- Interim Chief Product and Technology Officer at DonorsChoose.
- Completed Co-Active coaching training.
- A fifth-generation teacher who taught grades K through 8.
- Coached players and teams to winning national championships, and competed at world championships.
- Keynote speaker at ScotSoft in Edinburgh, addressing technology, finance, and government leaders.
- Creator of Saboteurs and Allies and Learned Resilience, whose pages rank first on Google for more than 100 search terms.
What Shapes His Coaching
Earning the trust of wary horses taught CD to listen before words, a practice explored in Non-Verbal Attunement. A chance encounter with the Dalai Lama later showed him how deep that connection can run between people. Both experiences shape how he coaches today: presence first, then questions, then growth.
Ways We Might Work Together
Coaching
CD coaches CEOs, CTOs, CFOs, founders, VPs, and other leaders, as well as managers and individual contributors. Clients come from tech, biotech, and other fields. Coaching often supports them through transitions, setbacks, and stretch goals. His approach draws on Co-Active coaching training, years as a K-8 teacher, and decades of coaching athletes and teams. Coaching often explores the Inner Voices that hold us back, builds Learned Resilience, and turns insight into small, repeatable practices.
Advising and Interim Leadership
CD advises founders and executives on engineering, product, process, and culture. He has helped eleven disruptive tech companies through existential crises. Seven became unicorns, together exceeding $400 billion in peak valuation. He currently serves as interim Chief Product and Technology Officer at DonorsChoose. Advising may focus on hiring and onboarding rituals, decision-making, development processes, or weathering storms.
Speaking
CD speaks on continuous innovation, Learned Resilience, inner voices, and leading through uncertainty. In 2012, he gave the keynote at ScotSoft in Edinburgh, drawing on his time leading engineering at IMVU, the company behind The Lean Startup. That talk now lives on as Continuous Innovation Rituals.
Writing and Collaboration
CD welcomes collaborations on articles, frameworks, and books exploring human transformation. Many pages on this site grew from conversations with leaders, coaches, and thinkers. Fresh perspectives are how these ideas keep evolving.
When Working With CD May Be a Good Fit
Every coach and advisor brings a distinct lens. Working with CD may be a good fit when:
- A founder or executive is leading through an existential crisis, a pivot, or rapid growth.
- Inner voices are holding back someone’s best work, or leaving them feeling it’s never good enough, whatever they achieve.
- A leader is stepping into a bigger role, or a new manager is leading people for the first time.
- A CEO, CFO, or founder wants a thinking partner on engineering, product, or technology decisions.
- A team needs better rituals for hiring, onboarding, feedback, or decision-making.
- Someone wants resilience that raises their baseline, rather than simply bouncing back.
When another lens would serve someone better, CD is glad to say so and suggest where to look.
How CD Works
- Listening first: understanding before advising, and asking before telling, much like the lesson from horses.
- Process over blame: when something goes wrong, we look at the process before we look at people, often with 5 Whys.
- Naming inner voices: recognizing the saboteurs behind self-doubt and strengthening the allies that move us forward, drawing on Saboteurs and Allies.
- Right-sized experiments: building resilience through small stretches, reflection, and learning with the THRIVE Loop.
- Small steps: change sticks best in small, shared increments, as Atomic Rituals explores.
- Challenge with care: serving people well sometimes means stretching them, not simply pleasing them.
- No single mantra: every person and organization is different, so no framework is applied rigidly.
Experience
Over several decades, CD has led engineering and product teams through rapid growth, pivots, acquisitions, and IPOs, at companies including Softlab, BroadVision, Intuit, Yahoo, IMVU, Twitch, Pure Storage, Prosper, and Hum Capital. Along the way, he has helped many organizations change how they build software. For the full journey, you might read Against All Odds and About CD.
Starting a Conversation
If something here resonates, an introductory call is a simple way to explore whether working together makes sense. There is no obligation. You might schedule an introductory call or send a message.
Either way, thank you for exploring. Discovering what matters to you is where every good conversation begins.