Principal Product Manager

Role overview

A senior product leadership role focused on owning retention strategy end-to-end for a SaaS platform serving small businesses, nonprofits, and entrepreneurs. The position acts as the single-threaded owner of customer value, shaping how AI surfaces meaningfully inside the product so users experience a faster, more intuitive path to results. It's a strategic, high-ambiguity role that combines roadmap ownership, experimentation, and cross-squad leadership without direct reports.

Responsibilities

• Define and own the retention strategy, translating high-level targets into squad-level metrics and experiments the team can directly move
• Drive measurable customer outcomes across net revenue retention, product engagement, and satisfaction, using data to prioritize ruthlessly
• Embed AI into the product experience so customers get a seamless, intelligent helper without needing AI expertise themselves
• Champion AI-assisted product development practices across research, prototyping, and iteration to accelerate learning
• Partner with engineering, design, marketing, and customer-facing teams to translate customer pain into clear requirements
• Mentor other product managers and cross-functional partners, raising the bar on product thinking through influence and direct feedback
• Communicate strategies, tradeoffs, and roadmaps clearly to executive audiences, defending decisions with data while staying open to challenge

Requirements

• 8+ years of product management experience in SaaS, ideally with small business or prosumer customers, leading complex, ambiguous problem spaces
• Hands-on familiarity with deploying large language models in production, plus a sharp sense for when AI adds value and when it gets in the way
• Strong written and verbal communication skills, comfortable switching between technical discussions with engineers and executive-level storytelling
• Deep comfort with quantitative analysis and qualitative customer research, able to pull insights from dashboards and direct conversations alike
• Demonstrated ability to lead through influence in a squad-based model, giving kind, direct feedback and building shared accountability
• Genuine customer obsession, including willingness to jump into support tickets or user calls to find the "why" behind friction

Nice to have

• Background in email marketing, marketing automation, or product-led growth
• Direct experience with prompt engineering or retrieval-augmented generation pipelines
• Prior ownership of growth-focused initiatives such as onboarding, monetization, or retention