Top Tech Jobs & Startup Jobs in Boston, MA

Own the vision, strategy, roadmap, and business growth of Tailscale’s Workload Connectivity product. Lead Kubernetes, ephemeral workload, AI agent, and cloud infrastructure connectivity initiatives; define developer experiences, pricing, packaging, success metrics, and integrations. Partner with engineering, design, operations, and go-to-market teams while engaging technical customers and guiding products from strategy through adoption and revenue impact.

Own and grow Tailscale’s analyst relations program by managing analyst inquiries, briefings, evaluations, research participation, and relationships. Synthesize analyst intelligence and market trends into recommendations for Product Marketing, Product, Engineering, and leadership. Develop analyst-facing materials, support market research, track program effectiveness, and strengthen the company’s positioning across cybersecurity, networking, infrastructure, AI, and emerging technology markets.

Own the vision, strategy, and roadmap for Tailscale’s Identity portfolio, including authentication, authorization, SSO, SCIM, access policies, and user management. Lead admin and end-user experiences across the console, API, and clients. Partner with engineering, product, and design, develop customer insights, and translate customer, support, and competitive signals into priorities. Ensure identity services are secure, reliable, intuitive, and integrated across Tailscale’s platform.

Own the vision, strategy, roadmap, and operator experience for Tailscale’s networking features, including App Connectors, DNS, Funnel, and Tailscale Services. Partner with go-to-market, customer success, and solutions engineering teams on strategic customer commitments. Develop customer insights, define product requirements, launch products, and iterate using data. Simplify complex networking systems through effective object models, defaults, configuration experiences, documentation, and error messaging.

Own and improve Tailscale’s software release management process, including release cadence, readiness criteria, rollout coordination, tooling, runbooks, go/no-go decisions, and operational metrics. Partner with engineering, product, TPM, and support teams to identify risks, coordinate planning, maintain release schedules, and drive scalable process improvements. Requires strong technical fluency in software delivery, deployment pipelines, branching, feature flags, and production operations.

Lead and mentor software engineering teams across multiple product pods. Provide technical direction, oversee production services and operational readiness, manage on-call and incident response, support hiring and career development, and drive cross-functional planning and delivery. The role requires strong people-management experience, technical judgment, production-service expertise, and the ability to work asynchronously in a distributed startup environment.

Develop and improve Tailscale’s security and privacy features, identify and resolve technical vulnerabilities, conduct security audits, perform threat modeling, and guide engineering teams on secure coding. The role spends at least half its time writing software and requires knowledge of application security, web vulnerabilities, client-side security, API flaws, cryptography, and networking protocols.

Build and maintain core billing software, including subscription and usage-based pricing, metering, rating, reconciliation, reporting, and third-party billing integrations. Ensure billing data integrity, observability, reliability, and high availability. Collaborate with product, finance, sales, support, and engineering teams on custom billing requirements, lead incident response, contribute to architecture and design reviews, and mentor engineers.

Own and scale Tailscale’s Product operations, including roadmap health, launch readiness, documentation, onboarding, feature request management, customer insight systems, operating rhythms, and product metrics. Partner with Product, GTM, Support, Data, and company leadership to identify operational gaps, establish standards, influence prioritization, and build scalable systems. The role requires autonomous execution, strategic judgment, cross-functional alignment, and strong communication in a remote-first environment.

Build and evolve Tailscale’s customer-facing documentation platform, docs-as-code tooling, content publishing pipelines, API documentation, and search infrastructure. The role includes full-stack development, CI/CD and automated testing, platform scalability, cross-functional collaboration with engineering, product, design, research, and growth teams, and engagement with open-source contributors. The engineer will also research documentation trends and consider how LLMs consume and interact with published content.