Principal Product Manager, Tax Platform

Gusto Gusto · Fintech · Toronto, ON +3 · Remote · Product Management

Product Manager for Gusto's Tax Platform, focusing on strategy, roadmap, and execution of core systems for tax calculation, tracking, payment, reconciliation, and filing. The role involves modernizing legacy systems, ensuring accuracy, scalability, and resilience in a regulated fintech domain, and partnering with various teams. Experience with AI-driven features is a plus.

What you'd actually do

  1. Own the strategy, roadmap, and execution for foundational Tax Platform systems, with responsibility for shaping platform direction across multiple quarters and years.
  2. Define and evolve a clear Tax Platform strategy that ladders into Gusto’s broader Tax strategy, bringing clarity to ambiguous problem spaces and guiding day-to-day decisions around prioritization, sequencing, and tradeoffs.
  3. Partner closely with Engineering, Compliance, Legal, CX, Data Science, and Product teams to align priorities, unblock dependencies, and drive adoption of shared platform capabilities.
  4. Translate between platform work and customer and business outcomes to help engineering teams understand impact and help stakeholders understand the value and tradeoffs of platform investments.
  5. Tie platform initiatives to customer outcomes by using data, domain expertise, and partner input to prioritize work that improves accuracy, timeliness, trust, and operational reliability.

Skills

Required

  • Product management experience
  • Platform team ownership
  • Strategy and roadmap development
  • System-level thinking
  • Navigating ambiguity
  • Making tradeoffs
  • Modernizing critical systems
  • Working in regulated domains (fintech, payroll tax, HR, legal tech)
  • Partnership with engineering teams
  • Translating between technical and business outcomes

Nice to have

  • Experience building AI-driven features

What the JD emphasized

  • 8+ years of product management experience
  • meaningful ownership of platform teams
  • strategy and multi-year initiatives
  • complex, multi-product environments
  • cross-team dependencies
  • internal platform customers
  • Strong system-level thinking
  • product judgment
  • navigate ambiguity
  • make hard tradeoffs
  • drive clarity
  • evolving or modernizing critical systems
  • balancing short-term delivery with long-term platform health and risk reduction
  • regulated or compliance-sensitive domains
  • deep appreciation for accuracy, auditability, and customer trust
  • partner closely with engineering teams
  • translate between platform decisions, customer impact, and business outcomes
  • strong POV on building products in the age of AI
  • experience building AI-driven features is a big bonus