Fractional Product Leadership

Senior product leadership for teams that aren't ready for a full-time hire.

Most organizations I work with have the right people and real ambition. What they are missing is the system: a clear product direction, the data infrastructure to measure progress, and the organizational habits to make good decisions consistently. Winters Product Group builds that structure. Fifteen-plus years doing it from scratch at Amazon, Apple, Google, and Chewy. Engagements structured for results, not for billable hours.

How I Work

Three engagement models, each designed around what the work actually requires.

What You Get

Every deliverable below is designed to outlast the engagement. The goal is not a report. It is a system your team runs without me.

  • Product strategy and roadmap development. Strategy work should produce decisions, not documents. I work from customer research, competitive context, and real business constraints to build a roadmap your team understands and can execute against. The prioritization model travels with the team. When I leave, your PMs know how to run the process without escalating every tradeoff to leadership.

  • Quantitative prioritization frameworks. Most teams prioritize by instinct, momentum, or whoever made the strongest case in the last sprint review. I built a quantitative prioritization system at Chewy that standardized decision-making across 20+ product teams and eliminated the peak-season escalation cycles that had been consuming leadership bandwidth for years. The framework survived my transition out of the role because it was built to be owned by the team, not by me.

  • Data infrastructure and analytics strategy. If your team is making product decisions without reliable data, or spending engineering cycles on measurement infrastructure that doesn't surface the right signals, that's where the work starts. At Amazon, I led the re-architecture of an operational metrics platform used daily by 30,000 people across 300+ global fulfillment sites, cutting load times from three minutes to five seconds and enabling decisions that contributed to hundreds of millions in efficiency gains. Good analytics infrastructure is a product decision. I treat it like one.

  • Team coaching and performance management. Leadership gaps rarely look like open headcount. They look like PMs who are technically capable but not operating at the right level, managers who haven't learned to delegate, and teams that wait for a senior leader to make the call. I've managed product organizations of 13+ people across multiple time zones, coached 20% of my direct reports to promotion, and turned around 30% of underperformers through direct feedback and structured development plans. I work with your team directly, not around them, because the goal is capability that outlasts the engagement.

  • AI/LLM workflow integration for product teams. AI tooling is moving faster than most product teams can evaluate it. I built and ran Chewy's AI enablement program across 20+ product teams, developing the evaluation criteria, workflow designs, and internal playbooks that made LLM adoption practical and durable. Teams reclaimed 20 hours per week in analyst overhead in the first phase, and the frameworks held because they were built around how teams actually worked, not around what the tools could theoretically do. The goal is never AI for its own sake. It's sustainable gains that hold up once the engagement ends.

Track Record

Numbers from real work, not projections.

$325M+ In Efficiency Gains Delivered
30K+ Daily Users on Platforms Built
96% Customer Satisfaction at Apple Watch Launch
50% Reduction in Audit Cycle Time
20+ Product Teams Enabled on AI/LLM Workflows
15+ Years of Product Leadership

Who I've Worked With

Enterprise organizations and early-stage clients. The problems are different. The approach isn't.

Amazon

Enterprise analytics platforms, supply chain optimization, ML and computer vision integration, and global fulfillment operations across 300+ sites.

Apple

New product launch strategy for Apple Watch 1.0, contact center product development, and platform integrations deployed across 2,000+ support agents worldwide.

Google

Technical e-commerce partnerships and product listing ads at scale, managing the Google–Walmart relationship across 10,000+ daily product listings generating $10M+ monthly.

Chewy

Compliance analytics, executive reporting infrastructure, product-led growth, and AI/LLM enablement across the full product organization.

Winters Product Group

Fractional product leadership and advisory for non-profits, retail, and e-commerce businesses in the Pacific Northwest. Engagements ongoing since November 2025.

Let's Talk

If you're building something that matters and need senior product leadership to get it right, reach out. The first conversation is straightforward: you explain the problem, I tell you honestly whether I can help.