Senior Software Engineer, AI-Driven Systems

Thimble is investing in the next generation of its insurance platform. The Senior Software Engineer will build durable workflows and services, lead platform migration patterns, and develop AI-native tooling while shipping production code in Node.js and TypeScript.

Responsibilities

• Design and build the durable workflows and services that will replace our current event-driven flows, defining service boundaries, state ownership, idempotency, and retry semantics
• Use of agentic coding tools on hard problems: setting up context, breaking down problems, and verifying output
• Write and ship production code in Node.js and TypeScript every day, using agentic coding tools (Claude Code and similar) as your primary way of working
• Define the reference patterns (service templates, shared libraries, code generators) that every rebuilt service follows
• Plan and execute the migration in increments that keep production running, with tested rollbacks
• Build and maintain the tooling around our AI workflow: MCP servers, evaluation scripts, and automated checks that hold AI-generated code to the same bar as hand-written code
• Instrument services with metrics, alerts, dashboards, and tracing, and own production incidents end to end
• Make targeted changes in our React and Angular applications when backend work requires them
• Partner with product, growth, and other engineers, and contribute to code reviews and architecture discussions

Preferred

• Hands-on experience with a durable execution or workflow orchestration engine, in any language
• You've built or contributed to an MCP server, an agent harness, an evaluation suite, or a multi-agent system, whether as a side project, open source, or an internal tool
• Experience in InsurTech, FinTech, or another regulated industry in a similar environment to our tech stack
• Workflow orchestration engines
• MCP server development
• Agent harness development
• Evaluation suite development
• Multi-agent systems
• InsurTech experience
• FinTech experience
• Regulated industry experience

Benefits

• Fully remote company
• Thimble Fridays! (out of office at 12:00pm local time)
• Comprehensive health, vision, and dental coverage
• 401(k) auto enrollment and matching (100% of the first 3% and 50% of the next 3%)
• PTO: 20 days vacation + 12 company-wide holidays + 8 floating days + 1 VTO (Volunteer Time Off) + unlimited sick time
• Parental Leave: 100% paid 12 weeks + 2 weeks gradual return
• Computer choice of Mac or PC
• Work from home setup reimbursement
• Monthly co-working space and/or child care reimbursement
• Monthly ClassPass credit
• Quarterly wellness reimbursement
• Other health & wellness perks including: One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate
• Virtual events, happy hours, trivia, and fun!

Company

• On-demand small business insurance broker
• New York, New York, USA
• https://www.thimble.com/
• Founded in 2015
• 11-50 employees

Qualifications

• Strong backend engineering with production experience in Node.js and TypeScript
• Hands-on experience building and operating distributed or event-driven systems, and a working understanding of how they fail
• Experience using AI tools to drive a large code migration at scale (framework upgrade, service rewrite, language port)
• Curiosity about agent harnesses, MCP, and A2A protocols; production deployment of agents is not required
• Experience contributing to a migration or re-platform on a live system
• Comfort reading unfamiliar code and data models and spotting problems in them
• Enough frontend literacy to trace a problem from the UI down to the service layer
• Clear written communication and comfort working in a remote, async-friendly environment
• Hands-on experience with a durable execution or workflow orchestration engine, in any language
• You've built or contributed to an MCP server, an agent harness, an evaluation suite, or a multi-agent system, whether as a side project, open source, or an internal tool
• Experience in InsurTech, FinTech, or another regulated industry in a similar environment to our tech stack

Required skills

• A2A Protocol, AI-Assisted Code Migration, Agent Harnesses, Distributed Systems, Event-Driven Architecture, InsurTech and FinTech, Live-System Migration, MCP, MCP Server Development, Node.js, TypeScript, Workflow Orchestration