Senior Product Manager, Tax Payments and Filing

Role overview This senior product role leads the strategy and execution for tax payments and filing systems that serve hundreds of thousands of small and medium businesses. The work centers on internal-facing tooling, automation, and AI-enabled platforms that keep compliance accurate amid constant regulatory change, partnering closely with Operations, Compliance, and engineering teams who are the primary internal customers. It is high-leverage product leadership at the core of a regulated financial workflow where correctness is non-negotiable.

Responsibilities - Define the investment strategy and long-term direction for tax compliance capabilities, deciding where to place bets and how to sequence them for maximum leverage - Partner with Operations, Compliance, and engineering as primary internal customers and collaborators, building trusted cross-functional relationships - Build automation, tooling, and system improvements that remove manual work and scale with rapid regulatory shifts - Use data to surface the highest-leverage opportunities, set goals, and measure outcomes against them - Prototype, design, and ship solutions that pair sharp product judgment with AI-native craft, treating AI as a co-builder - Translate ambiguity into clear execution plans with deliberate prioritization tradeoffs the team can rally around

Requirements - 5+ years of hands-on product management experience, including ownership of internal-facing platforms, tooling, or operational systems - Track record of driving leverage through automation, tooling, or system improvements that removed real work - Strong technical fluency and genuine partnership with engineering, with comfort operating in complex codebases - Experience in a compliance-driven or highly regulated domain where a regulator or government agency is effectively a stakeholder (e.g., financial services, banking, insurance, tax, healthcare, or benefits) - Hands-on experience applying AI and automation to product work - Ability to bring structure to ambiguity, define direction, sequence work, and make prioritization tradeoffs using clear frameworks

Nice to have - Experience working alongside Operations and Compliance functions as internal stakeholders - Familiarity with workflows that interact with government agencies or regulatory bodies

Benefits and work setup - Full-time position with competitive base pay, benefits, and equity for all full-time employees - Hybrid expectations of roughly 2-3 days per week in designated metro offices for onsite employees, with remote work available across the US and Canada where approved - Requires a secure, reliable internet connection when working outside of office locations - Reasonable accommodations offered to candidates with disabilities throughout the hiring process - Mission-driven environment focused on serving small and medium businesses