Lead Technical Program Manager

About Taskrabbit:

Taskrabbit is a marketplace platform that conveniently connects people with Taskers to handle everyday home to-do's, such as furniture assembly, handyman work, moving help, and much more.

At Taskrabbit, we want to transform lives one task at a time. As a company we celebrate innovation, inclusion and hard work. Our culture is collaborative, pragmatic, and fast-paced. We're looking for talented, entrepreneurially minded and data-driven people who also have a passion for helping people do what they love. Together with IKEA, we're creating more opportunities for people to earn a consistent, meaningful income on their own terms by building lasting relationships with clients in communities around the world.

Taskrabbit is a hybrid company with employees distributed across the US and EU and a Built In - Best Places to Work (2022, 2023, 2024) continually ranked across multiple national and regional categories. Join us at Taskrabbit, where your work will be meaningful, your ideas valued, and your potential unleashed!

This role operates on a hybrid schedule requiring two days of in-office collaboration per week. The position can be based in either our San Francisco office or our new New York City office (opening March 2026).

About the Role

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.

What You'll Do

• 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

Who You'll Work With

• Platform and system architects
• Engineering Managers
• Product Managers
• Backend, frontend, mobile, QA, and infrastructure engineers
• Senior Engineering and Product leadership

What We're Looking For

Required Experience

• 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)
• Experience working as a professional software engineer

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

Compensation & Benefits:

At Taskrabbit, our approach to compensation is designed to be competitive, transparent, and equitable. Total compensation consists of base pay + bonus + benefits + perks.

The base pay range for this position is $125,000- $165,000. This range is representative of base pay only, and does not include any other total cash compensation amounts, such as company bonus or benefits. Final offer amounts may vary from the amounts listed above and will be determined by factors including, but not limited to, relevant experience, qualifications, geography, and level.

You'll love working here because:

• Taskrabbit is a Hybrid Company. We value flexibility and choice but also stay committed to regular in-person connection.
• The People. You will be surrounded by some of the most talented, supportive, smart, and kind leaders and teams -- people you can be proud to work with!
• The Diverse Culture. We believe that we make better decisions when our workforce reflects the diversity of the communities in which we operate. Women make up half of our leadership team and our diversity representation is above that of the tech industry average.
• The Perks. 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. Benefits vary by country of employment.

Taskrabbit's commitment to Diversity and Inclusion:

An Active Commitment to Equity within our Company and Platform. We are an inclusive community where all who share our mission and values belong. Our diverse team represents the communities we serve, breaking down systemic barriers, and transforming lives- one action at a time.

Taskrabbit is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, ancestry, citizenship, sex, gender, gender identity, sexual orientation, age, marital status, military/veteran status, or disability status. Taskrabbit is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities.

Taskrabbit will consider for employment all qualified applicants with criminal histories in a manner consistent with applicable law.

Taskrabbit will never use text or chat applications to conduct interviews. We have a thoughtful and interactive interview process that includes an initial recruiter phone screen and several video-based interviews with our hiring teams. Communications will always be conducted by taskrabbit.com domain names.