Top Tech Jobs & Startup Jobs in Boston, MA

Lead resolution of high-severity post-sales escalations: investigate and reproduce complex networking and software issues, run customer calls, collect logs and evidence, create engineering-ready handoff packages, identify systemic patterns, and improve tooling and runbooks to raise Support's technical capability.

Partner with Account Executives to drive new commercial business by leading technical discovery, architecture design, demos and POCs. Guide complex deals, build scalable enablement and provide product/market feedback. Blend deep networking and security expertise with sales acumen to support quota attainment.

Lead the dataplane product vision and roadmap for Tailscale, owning connectivity features (WireGuard, relays, subnet routing, exit nodes, connectors), performance/reliability SLOs, regional relay capacity, operator tooling (console/CLI), and enterprise/regulatory deployments. Partner with engineering, GTM, and customers to drive production traffic commitments and improve connectivity across diverse NATs, OSes, carriers, and networks.

Join a remote Strategic Projects engineering team to turn AI-native prototypes into production-grade services. You will harden demos (LLM gateways, proxies, sandboxes), implement observability, error handling, and security practices, work with reference customers on integrations, and ensure agent-generated code meets production review and operational standards.

Build and maintain production-grade dbt data models and end-to-end data pipelines. Collaborate with Finance, Engineering, Sales, and Product to deliver reliable reporting, analytics, and scalable solutions, reducing manual workflows and ensuring data accuracy.

Build and lead Tailscale's Strategic Sales organization targeting enterprises (10,000+ employees). Personally own and close complex, multi-stakeholder six- to eight-figure SaaS deals, recruit and coach 3–5 Strategic AEs, design outbound territory and playbooks, drive account planning, forecasting, pipeline generation, and cross-functional GTM alignment with Product and Engineering.

Own the end-to-end developer experience for embedding Tailscale into applications: define reference architectures, SDK and CLI roadmaps, golden paths, docs, examples, and onboarding. Partner with engineering, internal dogfood teams, GTM, and external partners to prioritize and ship developer-facing SDK, API, and CLI features that reduce friction from prototype to production.

Manage and mentor multiple small engineering pods building and operating the control plane. Provide technical leadership, drive cross-functional product outcomes, hire and grow engineers, oversee on-call and incident response, and ensure high-availability production services while fostering an inclusive, remote-friendly engineering culture.

Design, build, and operate Tailscale's global Funnel and DERP relay infrastructure. Improve networking features and dataplane in open-source client code, ensure scalability and reliability with SRE/DevOps practices, troubleshoot complex network issues, integrate observability and incident response, and collaborate across engineering and product teams with a security-first approach.

Own end-to-end sales compensation operations: process and audit monthly commissions, administer compensation platform configuration, build financial and scenario models, deliver recurring attainment and payout analytics, support quota and territory planning, resolve commission disputes, and drive systems automation and cross-functional integrations to improve scalability and data quality.