{"id":83933,"url":"https://alion.io/job/tailscale-software-engineer-ai-enablement-2","title":"Software Engineer, AI Enablement","company":{"id":584,"name":"Tailscale","domain":"tailscale.com","url":"https://alion.io/company/tailscale","size_band":"501-1000","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Greenhouse","truth_index":{"grade":"A","score":89,"open_postings":7,"ghost_share":0,"stale_share":0,"repost_share":0.714,"time_to_fill_p50_days":42,"computed_at":"2026-10-31T05:58:55Z"}},"role":"Backend","role_family":"Backend","seniority":"senior","employment_type":null,"work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"board_field","remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["United States"],"countries":["US"],"hiring_countries":["US"],"hiring_countries_total":1,"salary":{"min":163000,"max":226000,"currency":"USD","period":"year","gross":null,"usd_annual":226000},"salary_estimate":null,"experience_years_min":5,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"Claude Code","optional":false},{"name":"LLM Guardrails","optional":false},{"name":"OpenAI Codex","optional":false},{"name":"Go","optional":true},{"name":"Platform Engineering","optional":true},{"name":"Python","optional":true},{"name":"Rust","optional":true},{"name":"Wi-Fi","optional":true}],"status":"live","first_seen_at":"2026-07-24T21:24:55Z","employer_posted_date":"2026-10-19","last_verified_at":"2026-10-31T07:10:56Z","board_verified":true,"closed_at":null,"days_open":98,"trust":{"level":"ok","repost_count":2,"flags":["repost"],"days_open":98},"description":"Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!\nAbout Tailscale \nTailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.\nAbout the Role\nWe're seeking a talented and motivated full-time Software Engineer, AI Enablement to help Tailscale's engineering organization get the most out of AI-assisted development. You'll join a small, high-leverage team reporting to our co-founder, working alongside our first AI enablement engineer to build the tools, workflows, and practices that help every engineer at Tailscale build faster and more safely with AI. This is a foundational role - you'll have real latitude to shape what AI enablement means here as we scale, with direct visibility into how the whole engineering org adopts these tools.\nKey Responsibilities\nPartner with engineering leadership and Tailscale's technical staff to define and drive our internal AI-enablement roadmap.\nWork closely with the team building Aperture by Tailscale, our AI gateway used both internally and offered as a product.\nBuild and iterate on the tools, workflows, and shared practices that help engineers get real value from coding agents - and evaluate new models and tools, making clear calls on what we adopt.\nPartner with engineering and non-engineering teams to find high-leverage opportunities to apply AI - this is a support function, so success means other teams shipping faster because of what you've built.\nEstablish the guardrails, review practices, and documentation that make AI-generated code safe to ship, and act as the internal advocate who helps teams adopt good practices without mandating a single tool.\nTrack adoption and measure the real impact of AI tooling on velocity and quality, and report back to leadership.\nWhat We Are Looking For\n5+ years of professional software engineering experience\nGenuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) - real power-user experience, not occasional use\nExperience building and shipping internal tools or developer-facing automation\nStrong written and verbal communication and internal advocacy skills - comfortable teaching, writing, and influencing engineers at very different comfort levels with AI tooling\nA balanced approach - trying to get people to use AI effectively and safely where appropriate. We don't have an 'AI mandate'; we believe that if we make AI both easy to use and safe, people will choose to use it when appropriate.\nComfort with ambiguity and self-directed prioritization on a small, still-forming team\nProduct or systems thinking - able to identify and prioritize high-leverage opportunities, not just execute a pre-set roadmap\nNice to Have\nPrior experience in developer experience, platform engineering, or internal tooling\nExperience evaluating or benchmarking LLMs and coding agents\nExperience with a systems language such as Go or Rust, in addition to Python\nBackground in security or code-review practices - helpful for reasoning about AI/agent-generated code, though you don't need to be a security engineer\nExperience in developer relations, technical evangelism, or customer-facing developer advocacy - the same skills that make someone effective in external DevRel translate well to driving internal AI adoption\nTechnical project management experience\nAs a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.\nUS Pay Range\n$163,000—$226,000 USD\nWhat We Offer\nAn inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.\n A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).\nComprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!\n Remote first company -most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.\nEmployer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.\nConnect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.\n\nSupport for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. \nPaid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! \n A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. \n Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).\nTailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.\nOur hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.\nPlease be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.","description_format":"text","description_chars":7366,"description_truncated":false,"requirements":{"experience_years_min":5,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":{"level":"phd","optional":false},"security_clearance":false,"languages":[]},"benefits":["Equity","Home office","Internet reimbursement","Parental leave","Professional development"],"hiring_locations":[{"name":"United States","iso":"US","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":["Network Security","VPN & Proxy Services"],"lifecycle":[{"event":"open","at":"2026-07-24T21:24:55Z"},{"event":"close","at":"2026-09-03T15:53:37Z"},{"event":"reopen","at":"2026-10-08T20:59:50Z"},{"event":"close","at":"2026-10-16T14:28:06Z"},{"event":"reopen","at":"2026-10-19T19:05:13Z"}],"visa":[{"country":"US","licensed_sponsor":true,"evidence":"H-1B filings in 12 months: 1","filings_12m":1,"filings_prev_12m":0,"green_card_filings_12m":0,"median_offered_wage_usd":212500,"route":null,"cap_exempt":false,"checked_at":"2026-10-29T16:27:21+00:00","sources":["US Department of Labor: LCA disclosure data (H-1B, H-1B1, E-3)"],"filings_for_role_12m":0}],"liveness":{"score":17,"band":"cold","label":"Long shot","p_open":1,"p_active":0.592,"p_room":0.28,"age_days":98,"expected_fill_days":42,"reasons":["conf:2","repost:2","velocity","win:tail","crowd:"],"computed_at":"2026-10-31T05:58:55Z"},"pay":{"stated_usd_annual":226000,"is_top_pay":true},"html_url":"https://alion.io/job/tailscale-software-engineer-ai-enablement-2","json_url":"https://alion.io/job/tailscale-software-engineer-ai-enablement-2.json","meta":{"generated_at":"2026-10-31T08:42:13Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":13036,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-11-01T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":584},"rest":"https://alion.io/mcp/rest/get_company?id=584"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Ftailscale-software-engineer-ai-enablement-2"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Ftailscale-software-engineer-ai-enablement-2"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Ftailscale-software-engineer-ai-enablement-2"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/tailscale-software-engineer-ai-enablement-2\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Ftailscale-software-engineer-ai-enablement-2"}],"agent":{"mcp":"https://alion.io/mcp/jobs","mcp_open":"https://alion.io/mcp/open","next":[{"tool":"get_job","arguments":{"id":83933}},{"tool":"search_jobs","arguments":{"company":"tailscale.com","detail":"compact"}},{"tool":"match_people","arguments":{"job_id":83933},"note":"people open to offers who fit this vacancy"}],"note":"The same data through MCP tools: https://alion.io/mcp/open needs no sign-in (compact searches, postings, people); https://alion.io/mcp with an Alion account has everything. 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