Senior Software Engineer, Taskrabbit

• 5+ years of professional software engineering experience, with a track record of leading complex work and influencing multiple teams
• Strong background in Ruby on Rails and typed Ruby (Sorbet), plus working knowledge of TypeScript, especially contract-driven type generation
• Solid SQL and data modeling skills (MySQL)
• Hands-on experience with async/event-driven systems (Kafka) and service or engine-boundary architecture
• A track record of building and owning observability and alerting for critical systems
• Strong communication skills, the ability to influence without authority, and real ownership over systems that affect marketplace supply and tasker trust

Desirable

• We're seeking a Senior Software Engineer to join our Tasker & Supply team, someone who doesn't just build, but raises the quality bar across our entire ecosystem. You'll be instrumental in shaping the experience of the taskers who power our marketplace. Your work will focus on onboarding, category/skill eligibility, and marketplace matching through our Ruby on Rails engine architecture, as well as critical work moving our service contracts toward strongly-typed TypeScript bindings
• Architect: Work with the engineering manager and architects to define the multi-quarter technical roadmap for Tasker & Supply (onboarding, category eligibility, geography, matching). Drive strategy, tackle tech debt, and evolve our engine boundaries, gateway contracts, and data models
• Tech Lead: Lead complex, cross-team initiatives around marketplace liquidity and supply-demand matching
• Solver: Take ambiguous, high-stakes business goals and turn them into clear technical strategies, designs, and experiments
• Operational Excellence: Improve reliability and observability (Datadog, Kafka) for onboarding, matching, and supply-side systems. Own the hard production debugging and push for real, systemic fixes
• Multiplier: Be our go-to Ruby/Sorbet expert. Champion good testing and AI practices, mentor other engineers, and write documentation people actually use
• Champion AI-Driven Development & Contract Binding: Lead adoption of Spec-Driven Development with AI tools, and help move our service integrations toward strongly-typed TypeScript contracts