Job Description

About Tailscale 

Tailscale is building the new Internet 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.

About Tailscale 

Tailscale is building the new Internet 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.

About the Role

We are looking for a technical leader and program scaler to manage our developer advocacy and relations team and help oversee the strategic direction of developer advocacy at Tailscale. You’ll manage a small but growing team that includes our Lead Developer Advocate, Senior Community Manager, and Technical Content Manager and together scale our Developer Marketing, Relations, and Advocacy across North America, Europe, and beyond. 

This is a player/coach role: you’ll not only work with your team to set a vision and roadmap for developer marketing at Tailscale, but you’ll also be expected to roll up your sleeves, speak at conferences, build demos, and represent Tailscale in developer communities and spaces directly.

The ideal candidate has deep empathy for technical users, is highly technical themselves and uses Tailscale, has strong systems-thinking and program management skills, and a track record of scaling developer-facing programs with measurable impact. In many ways, you will be the custodian of Tailscale’s first impression and brand. 

Responsibilities

• Lead the team: Manage, mentor, and partner with our Lead Developer Advocate, Senior Community Manager, and Technical Content Manager
• Be a voice for Tailscale : Speak at conferences, run workshops, appear in webinars, and create demo-rich content for a global developer audience. We’re especially looking for someone who can be Tailscale’s leading voice in North America – both in person and feeding into our digital outlets. You’ll be complemented by a teammate who will cover this role in Europe.
• Scale our programs : Build repeatable programs to grow developer awareness, education, and engagement in North America, Europe, and beyond
• Get us in the right rooms : Improve our talk submission and speaker placement process for key conferences across DevOps, security, infrastructure, IT, and more
• Measure and grow : Define and track KPIs for developer marketing, relations, and advocacy (e.g., reach, content engagement, brand awareness, community growth, attribution to PLG funnel)
• Collaborate cross-functionally : Partner with engineering, product, growth, sales, customer success, solutions engineering, and marketing teams to ensure developer initiatives are strategic, measurable, relevant, and high-leverageEvolve our voice: Help shape how Tailscale shows up in the technical world with clarity, authenticity, and technical nerdiness

What We’re Looking For

• Proven expertise : Minimum of 5-8+ years in developer-facing roles, including 2+ years in a lead or senior role with a measurable track record of impact
• Technical aptitude : Experience using Tailscale and technical depth in networking, infrastructure, security, and/or developer tools
• Storytelling : Excellent public speaking and technical storytelling skills. Experience with conference CFPs and securing high-visibility speaking slots
• Program management : You think in systems, templates, and repeatable playbooks
• People management : A strong desire to be a best-in-class people manager. We want someone who is excited and passionate about being a people manager and has experience mentoring and developing DevRel talent
• International : Demonstrated success growing developer awareness outside of North America and measuring this impact
• Outcome-orientation : Familiarity with key Developer Marketing KPIs and a perspective on how best to track individual and team performance

It’s Nice If You Have

• You are a Tailscale power-user and already a Tailscale advocate
• Prior experience as a software engineer or SRE
• Strong presence on dev-focused platforms (e.g., GitHub, Mastodon, YouTube, Reddit, Stack Overflow)
• Experience building or contributing to open source communities
• Previous people management experience

US Pay Ranges$161,000—$201,000 USDCAN Pay Ranges$215,000—$269,000 CAD

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!

What We Offer

• An 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.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• 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.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
• Support 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. 
• Paid 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! 
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. 
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. 

Please 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 .

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