FAQ

Common questions

Everything you'd want to know before starting a coaching conversation. Don't see your question here? Ask directly.

What is product leadership coaching?

Product leadership coaching is 1:1 professional coaching for heads of product, VPs of Product, and CPOs who want to improve their strategic thinking, executive presence, and leadership effectiveness.

Unlike general leadership coaching, product leadership coaching is specific to the challenges of running a product team — setting vision, managing across engineering and design and GTM, navigating CEO and board dynamics, building team capability, and connecting product decisions to business outcomes.

Who is this coaching for?

I work with two types of clients:

  • First-time heads of product — VPs or directors stepping into product leadership for the first time who need to develop strategic thinking, executive presence, and an operating model that works at their company.
  • Founders — who need a strategic product thinking partner on strategy, pricing, AI-first transformation, and how to scale from founder-led product to a team-led product org.
How is coaching different from consulting?

Consulting delivers a specific output — a strategy document, an analysis, a recommendation. Coaching develops your capability to think and lead more effectively.

In coaching sessions, I help you work through challenges yourself, build your pattern recognition, and hold you accountable to what you committed to doing. That said, my advisory work does blur this line: document review, direct feedback on decks, and specific strategic input are all part of the engagement when they're useful.

What does a typical engagement look like?

A typical engagement is a monthly retainer that includes:

  • Weekly or bi-weekly 60-minute 1:1 sessions (video call)
  • Async access between sessions for quick questions and gut checks
  • Document review — decks, strategy proposals, job descriptions, pricing proposals

Sessions are driven by your agenda. We go where the work is most pressing that week — no fixed curriculum, no homework assignments.

How much does coaching cost?

I work on a monthly retainer basis. Pricing depends on engagement structure, session frequency, and the scope of advisory work involved.

The best way to understand what makes sense for your situation is to start with a 30-minute intro call — no commitment, no pitch. Book a time here.

How long is a typical engagement?

Most engagements run 3–6 months as a baseline — meaningful improvement in leadership effectiveness takes time to develop and embed. Many clients continue longer once they see the impact.

Advisory relationships for specific strategic work (e.g., pricing redesign, AI strategy) can be structured differently based on scope. There's no hard lock-in — but short engagements rarely move the needle the way sustained work does.

What makes you different from other product coaches?

The biggest differentiator is that I'm an active operator — not a retired executive. As SVP of Product at Siteimprove, I'm navigating the same AI transformation, executive alignment, pricing decisions, and org design challenges you are — right now, at scale.

I also have depth across multiple company stages. I've built products at Sendgrid pre-acquisition (scrappy startup execution), Twilio (enterprise platform scale), Contentful (interim CPO through a critical inflection point), and Siteimprove (leading an AI-first transformation of a PE-backed company). That range means I can meet you where you are — not just where I was.

What topics do you cover in sessions?

We work on whatever is most live and relevant for you. Common topics include:

  • Setting product vision and building a strategy narrative
  • Earning buy-in from CEO, board, and leadership peers
  • Managing a team you inherited vs. building your own
  • Structuring a roadmap that's defensible without being rigid
  • Pricing and packaging strategy (treated as a product problem)
  • AI-first product strategy and what's real vs. hype
  • Building a product operating model that scales
  • Navigating board presentations and investor conversations
  • Hiring and developing PMs
Do you work with clients outside the US?

Yes. All sessions are remote via video call. I work with clients across different time zones — the main constraint is finding a recurring weekly or bi-weekly slot that works for both of us.

How do I get started?

Book a free 30-minute intro call. There's no pitch — just a direct conversation about where you are and what you're working on. If it's a good fit, we'll talk about next steps from there.

Book an intro call →

Still have questions?

The best answer is a conversation.

Book a free 30-minute intro call. Ask what you need to ask. No pressure, no pitch.

Book a free intro call