Community Engagement and Advocacy Manager

Location: Remote (Canada) 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! About Tailscale Tailscale 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. About the Role The Community Programs team creates the spaces, programs, and opportunities that help our community thrive. We're looking for a Community Engagement and Advocacy Manager to help us strengthen relationships with the people who use, build with, and advocate for Tailscale. In this role, you'll own and grow three important areas of our community: the Tailscale Insiders advocacy program, our digital communities, specifically Discord and Reddit, and our Community Projects program. You'll focus on creating meaningful opportunities for community members to connect, contribute, share their expertise, and be recognized for the work they do. Whether that's helping an Insider find their next speaking opportunity, bringing Tailscale staff into conversations on Discord, or showcasing an exciting community-built project, you'll help turn community participation into lasting relationships and advocacy. You'll work closely with teams across Tailscale, including Developer Relations, Product, Engineering, Marketing, and Support, to connect community members with the right people, resources, and opportunities. We're looking for someone who genuinely enjoys working with people, understands what makes communities thrive, and can turn ideas into thoughtful, well-run programs. You don't need to be deeply technical, but you should be curious about technology and excited to learn from the people building with it. Key Responsibilities Insiders Advocacy Program Own the strategy, day-to-day operations, engagement, and ongoing growth of the Tailscale Insiders advocacy program. Build and maintain meaningful relationships with Insiders, understanding their interests, expertise, motivations, and how they want to participate in the Tailscale community. Develop recurring engagement opportunities that help Insiders connect with one another and with teams across Tailscale. Identify opportunities for Insiders to contribute through speaking engagements, technical content, community events, product feedback, testing, and other initiatives. Partner with internal teams to create clear pathways for Insiders to participate in company initiatives, ensuring opportunities are relevant and mutually beneficial. Identify and nurture emerging advocates across the Tailscale community, creating pathways for deeper participation and potential involvement in the Insiders program. Own the recruitment, onboarding, recognition, and ongoing engagement of Insiders, ensuring participants feel valued, supported, and connected. Gather feedback from program members and continuously improve the Insider experience. Track program participation, contributions, engagement, and outcomes to understand and communicate the impact of the program. Digital Communities: Discord & Reddit Own the strategy, day-to-day engagement, and overall community experience across Tailscale's Discord and Reddit communities, fostering welcoming, active, and inclusive spaces. Develop and execute engagement initiatives, including community events, AMAs, discussions, and member spotlights that encourage participation and connection. Partner with teams across Tailscale to bring staff into community conversations and create opportunities for meaningful engagement. Partner with Product, Marketing, and Developer Relations to plan and lead Discord and Reddit engagement around product launches, announcements, and key company initiatives. Own day-to-day community moderation, including enforcing guidelines, managing moderation tools and bots, coordinating volunteer moderators, and escalating sensitive issues to appropriate internal teams. Identify opportunities to improve community engagement, structures, and experiences based on member feedback and participation. Recognize and celebrate active members and contributors, creating opportunities for deeper involvement and advocacy. Monitor community conversations, feedback, and engagement metrics to identify emerging themes, share actionable insights with internal teams, and inform community strategy, product decisions, and program improvements. Community Projects Own the strategy, operations, and continued growth of Tailscale's Community Projects program, recognizing and amplifying projects built by our community. Develop and maintain a clear, repeatable process for discovering, submitting, reviewing, tracking, and showcasing community projects. Build relationships with project creators, understanding what they've built, their motivations, and how Tailscale can support and recognize their work. Partner with Developer Relations, Marketing, Product, and Engineering to identify opportunities to turn community projects into technical content, demos, documentation, social content, and community showcases. Create opportunities for project creators to share their work through community events, presentations, blog posts, videos, and other channels. Identify projects that demonstrate creative or emerging uses of Tailscale and help surface those examples to relevant internal teams. Develop thoughtful ways to recognize and reward contributors, ensuring builders receive visibility and credit for their work. Track program activity, project contributions, and outcomes to help demonstrate how community projects support advocacy, learning, and broader awareness of Tailscale as a platform. What We Are Looking For 3–5+ years of experience in community management, advocacy, community programs, developer communities, or related roles. Experience owning and growing community programs, including developing initiatives, coordinating stakeholders, and driving engagement. Proven ability to build meaningful relationships with community members, advocates, contributors, and internal teams. Experience managing and moderating online communities, including community guidelines, moderation tools, and maintaining healthy, inclusive environments. Strong written and verbal communication skills, with the ability to engage authentically and collaborate across teams. Excellent organizational and program management skills, with the ability to manage multiple priorities, work independently, and navigate ambiguity. Strong understanding of community engagement and advocacy, with the ability to identify opportunities, recognize contributors, and turn feedback into meaningful improvements. Genuine curiosity about technology and an eagerness to learn about Tailscale's products and community. Nice to Have Experience managing advocacy, ambassador, champion, or contributor recognition programs. Hands-on experience managing Discord, Reddit, or similar community platforms, including moderation bots and automation tools. Experience working with developers, open source, infrastructure, networking, security, or other technology-focused communities. Familiarity with community engagement and intelligence tools such as Common Room. Experience developing community programming such as AMAs, virtual events, member spotlights, and recurring engagement initiatives. Experience identifying and amplifying community stories, projects, or contributor achievements. Experience collaborating with Product, Developer Relations, Engineering, Marketing, or Support teams. Willingness and ability to travel occasionally to support community events, meetups, and other initiatives. As 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. CAN Pay Range $192,960 — $237,180 CAD 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. Employer-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. Connect 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. 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 $500 USD to customize your workstation to make it your own. 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). Tailscale 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. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. 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 https://tailscale.com/scam-awareness .