Lead Technical Program Manager

TaskrabbitSan Francisco, NY
8d$125,000 - $165,000Hybrid

About The Position

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. You’ll work closely with an architect, engineering managers, product managers, and developers to ensure this work is sequenced correctly, risks are surfaced early, and progress is transparent to senior leadership. This is a high-visibility role that requires strong technical judgment, excellent cross-functional leadership, and the ability to operate comfortably in ambiguity.

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 Haves

  • 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)

Responsibilities

  • 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

Benefits

  • Taskrabbit offers our employees with employer-paid health insurance and a 401k match with immediate vesting for our US based employees.
  • We offer all of our global employees generous and flexible time off with 2 company-wide closure weeks, Taskrabbit product stipends, wellness + productivity + education stipends, IKEA discounts, reproductive health support, and more.
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