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Taskrabbit Logo Taskrabbit · IT - Software Development

Lead Technical Program Manager

United States, New York 125000.00 - 165000.00 USD / Year · Job Posted January 22, 2026
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Job Description

Taskrabbit is undertaking a major platform evolution: transitioning critical parts of our core product from a large, monolithic Rails-based codebase to a more modular, event-driven services architecture. This role exists to own and drive that transition end-to-end. As Senior Technical Program Manager, Platform, you will be responsible for planning, coordinating, and delivering multiple parallel decomposition and migration workstreams.

Job Responsibility

  • Own the program to decompose portions of Taskrabbit’s monolithic Rails application into event-driven services
  • Drive planning and execution across multiple concurrent workstreams, including service extraction, data ownership changes, and event contracts
  • Partner closely with platform architects and engineering leaders to translate architectural direction into executable plans
  • Coordinate work across backend, frontend, mobile, and infrastructure teams
  • Facilitate regular planning rhythms to manage dependencies, surface risks, and unblock teams
  • Lead backlog grooming and sequencing to ensure migration work is aligned with product delivery
  • Identify and remove execution blockers, including unclear ownership, dependency conflicts, and resourcing gaps
  • Track and communicate progress, risks, and tradeoffs through weekly and monthly reporting to senior leadership
  • Ensure migration work maintains system stability, performance, and developer velocity throughout the transition
  • Help establish and evolve program-level operating rhythms, documentation, and source-of-truth artifacts

Requirements

  • 8+ years of experience in Technical Program Management or equivalent technical delivery roles
  • Demonstrated experience decomposing monolithic systems into services or modular architectures
  • Strong understanding of distributed systems, service boundaries, and dependency management
  • Proven ability to run complex, multi-team programs with significant technical risk
  • Experience facilitating Scrum of Scrums or similar cross-team execution forums
  • Comfortable operating at both the architectural and execution levels
  • Excellent written and verbal communication skills, especially with senior leadership
  • Demonstrated expertise with Agile frameworks (e.g., Scrum, Kanban) including backlog management, sprint planning, estimation, reviews, and retrospectives.

Nice to have

  • Experience with event-driven architectures and messaging systems (e.g., Kafka)
  • Familiarity with TypeScript-based backend services
  • Background working in polyglot environments (Rails, Node/TypeScript, etc.)
  • Experience modernizing legacy systems while continuing to ship product
  • Proven ability to design and maintain Jira configurations that support Agile (Scrum/Kanban boards, epics, story hierarchies)
  • Experience working as a professional software engineer

What we offer

  • Employer-paid health insurance
  • 401k match with immediate vesting
  • Generous and flexible time off with 2 company-wide closure weeks
  • Taskrabbit product stipends
  • Wellness + productivity + education stipends
  • IKEA discounts
  • Reproductive health support
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