Top Tech Jobs & Startup Jobs in Boston, MA

Partner with Account Executives to drive new commercial business by leading technical discovery, solution architecture, demos, and POCs. Guide complex deals, align technical and business objectives, provide product and GTM feedback, and build scalable enablement resources, demo environments, and solution blueprints for the SE team.

Build and maintain core billing systems: integrate third-party billing platforms, implement metering/pricing/rating for subscriptions and usage-based models, ensure accurate usage tracking, observability, and high availability, automate reconciliation and reporting, collaborate with product/finance/support, lead incident response and provide technical leadership.

Drive product positioning, messaging, launches, and sales enablement for Tailscale. Conduct customer research, competitive analysis, and create collateral, demos, and enablement to generate pipeline and support revenue teams.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for weaknesses, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security, incident containment, and technical security analysis while collaborating with engineering teams in a distributed startup environment.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, maintaining strong customer satisfaction, troubleshooting across operating systems, and partnering with Customer Experience, Product, and Engineering teams to improve user outcomes.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Apply and evolve the visual identity, create reusable templates and design systems, collaborate cross-functionally, present concepts, incorporate feedback, and manage multiple projects while delivering polished, production-ready work.

Serve as a technical, customer-facing engineer for strategic enterprise customers: lead onboarding, provide hands-on configuration and troubleshooting, run QBRs, drive adoption and expansion, relay customer feedback to product/engineering, and produce technical documentation to enable self-service and long-term success.

Create technical, growth-focused educational content (tutorials, implementation guides, demos, comparisons) that drives discoverability and product adoption. Work with product, engineering, and marketing to build hands-on examples, optimize content for search and AI discovery, refresh existing assets, and measure impact against quarterly growth metrics.

Develop and maintain Tailscale's Windows client and contribute to cross-platform client and backend code. Build UI and platform integrations using WinUI/Windows native frameworks, write unit and integration tests, implement Windows platform features while preserving compatibility, and collaborate asynchronously across a distributed engineering team.

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.