Coaching & Advisory

How we work together

Every engagement is different. But the foundation is the same: honest, direct coaching from someone currently inside a B2B SaaS company navigating AI transformation, pricing strategy, org design, and executive alignment. At scale, right now. Not from memory.

Engagement types

Two tracks, one core purpose

I work with first-time product leaders and founders. The problems are different; the approach is the same.

Track 1 — Coaching

First-time heads of product

For VPs and heads of product new to the role. The jump to product leadership is a category change, not a promotion. You're expected to operate strategically, earn executive credibility, and lead a team you didn't hire, often without a playbook. That's exactly what we work on.

  • Establishing executive presence with CEO and peers
  • Setting product vision and earning org-wide buy-in
  • Managing a team you didn't hire
  • Translating strategy into a real, defensible roadmap
  • Navigating your first board presentation
  • Building a high-performance product operating model
Track 2 — Advisory

Founders building product-led companies

For founders who need a strategic product thinking partner. Not a consultant with a deliverable, but an advisor who helps you think more clearly about the hardest product decisions.

  • Product vision and go-to-market alignment
  • Pricing and packaging strategy (treated as a product problem)
  • Transitioning from founder-led product to a dedicated team
  • AI-first product strategy and agentic workflow design
  • Hiring your first head of product
  • PLG to enterprise motion: what changes and what doesn't
The process

How an engagement works

1

Intro call

30 minutes. No pitch. We talk about where you are and whether this is a good fit.

2

Discovery

I get context on your company, team, role, and the specific challenges you're working through.

3

Regular sessions

Weekly or bi-weekly 1:1 calls, structured around whatever is most live and relevant right now.

4

Async support

Between sessions, I'm reachable for quick questions, document review, and real-time input when things move fast.

What sessions look like

Direct. Structured. Grounded in real work.

Sessions aren't therapy, and they're not lectures. We work through what's most pressing for you that week: a board presentation, a difficult stakeholder, a strategy decision you're second-guessing, a pricing conversation you need to lead.

I challenge your assumptions. I bring perspectives from what I'm navigating at Siteimprove and what I've seen across multiple companies. I ask questions that push you toward your own clarity, not just questions to fill time.

You leave with a clearer perspective, a decision made, or an action you're confident taking. Not a homework assignment.

📋

Common session topics

  • → How do I position product strategy in the next all-hands?
  • → My CEO keeps overriding roadmap priorities. How do I push back?
  • → I need to restructure my pricing. Where do I start?
  • → How should I structure a product narrative for a board deck?
  • → I'm inheriting a team with low PM craft. Where do I start?
  • → What should AI actually look like in my product?
Engagement structure

What's included

📞

Weekly or bi-weekly 1:1s

60-minute sessions on a consistent cadence. Structured around your agenda, not a fixed curriculum. We go where the work is.

💬

Async access

Between sessions, I'm available for quick questions, document review, or a gut check when you need a fast perspective on something moving now.

📄

Document review

Strategy decks, board presentations, pricing proposals, job descriptions. I review and give direct, specific feedback before they go out.

Pricing

A monthly retainer, not an hourly relationship.

I work on a monthly retainer basis. This keeps the relationship simple and means you're not thinking about the clock every time you reach out or want a second opinion on something.

Pricing depends on engagement structure, frequency of sessions, and the scope of the advisory work. The best way to understand what makes sense for your situation is to start with a conversation.

I take a limited number of clients at a time, which means I'm selective about who I work with, and you'll get real attention, not a templated program.

Book an intro call
What to expect

The engagement model

  • 📅 Monthly retainer, rolling, cancel any time
  • 🔁 Weekly or bi-weekly 60-min 1:1 sessions
  • 💬 Async support between sessions
  • 📄 Document review: decks, strategies, proposals
  • 👥 10 clients max, selective intake, real attention
Get started

Start with a conversation.

Book a 30-minute intro call. We'll talk through where you are, what you're working on, and whether coaching makes sense right now.

Book a free intro call