Leading Product with Confidence
This package is designed for product managers stepping into people leadership for the first time, as well as those already in the role who want a thought partner with real-world experience to pressure-test ideas and sharpen their approach. Over the course of our sessions, we'll work through the practical and strategic challenges that come with leading product teams - how to build credibility quickly, set direction without all the answers, navigate stakeholder dynamics, give feedback that lands, and develop the people around you while still driving outcomes. Each session is tailored to what you're facing right now. You'll bring the context; I'll bring frameworks, honest perspective, and pattern recognition from nearly two decades leading product at companies like KAYAK and Eventbrite. We'll work through real situations - a difficult conversation you're preparing for, a strategy you're trying to land, a team dynamic that isn't clicking - and leave each session with clarity and a concrete next step. What to expect: • Structured but flexible sessions built around your current challenges • Frameworks for common leadership moments: communicating strategy, managing up, giving feedback, building team trust • A thinking partner who will push back when it matters and tell you what they actually think • Shared resources and reading recommendations where relevant This is not a lecture series. It's a working relationship built around your growth as a leader.
What's included
This package is delivered over three live, 1:1 video sessions, each one hour. The format is conversational and human - there's no script or rigid agenda. You bring what's on your mind, and we work through it together honestly and openly. Some sessions will be strategic, some will be tactical, some will just be about thinking something through with someone who's been there. Clients are welcome to continue beyond the initial package as new challenges emerge - how we work together can adapt alongside you.
- A clearer sense of your leadership identity and how to show up in high-stakes moments
- Practical frameworks for difficult conversations, managing up, and building team trust
- A sharper, more confident way to communicate strategy and direction
- Honest perspective on the specific challenges you're facing right now
- A concrete next step or action plan from each session
Meet your expert

Vanessa K.
VP of Product | Marketplace & Consumer Tech Leader
I’m a product leader with 15+ years of experience building and scaling consumer platforms and marketplaces, including leadership roles at Eventbrite and KAYAK. I’ve always been drawn to the intersection of technology, creativity, and real human problems—helping teams turn ideas into products people genuinely connect with. My work has focused on product strategy, craft, and building strong, outcome-oriented teams.