Lead Technical Program Manager, Taskrabbit

• We’re looking for talented, entrepreneurially minded and data-driven people who also have a passion for helping people do what they love
• This is a high-visibility role that requires strong technical judgment, excellent cross-functional leadership, and the ability to operate comfortably in ambiguity
• 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

Desirable

• 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
• 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
• What Success Looks Like
• Clear, phased plans for monolith decomposition that teams can execute against
• Reduced coupling and improved ownership across services
• Predictable delivery of migration milestones without destabilizing the platform
• High trust and alignment across engineering, product, and leadership
• Transparent reporting that makes progress, risks, and tradeoffs easy to understand