Community Engagement and Advocacy Manager

About this role

Own and grow Tailscale’s Insiders advocacy program, Discord and Reddit communities, and Community Projects program. Build relationships with community members, create opportunities for participation and recognition, and partner with internal teams to turn community insights and contributions into lasting engagement.

About the company

Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.

The team

Community Programs team

What you'll do

• Lead strategy and operations for the Insiders advocacy program, digital communities, and Community Projects program.
• Recruit, onboard, recognize, and engage Insiders and emerging advocates.
• Create community events, discussions, AMAs, and other opportunities for member participation.
• Manage community moderation, guidelines, tools, and volunteer moderators across Discord and Reddit.
• Identify and showcase community-built projects, coordinating with internal teams on content and events.
• Monitor engagement and feedback, track program outcomes, and share actionable insights internally.

What we're looking for

• 3–5+ years of experience in community management, advocacy, community programs, developer communities, or a related field.
• Experience owning and growing community programs and coordinating stakeholders.
• Strong relationship-building, written and verbal communication, and organizational skills.
• Experience managing and moderating online communities and fostering inclusive environments.
• Ability to work independently, manage multiple priorities, and navigate ambiguity.
• Curiosity about technology and eagerness to learn about Tailscale’s products and community.

Nice to have

• Experience with advocacy, ambassador, champion, or contributor recognition programs.
• Hands-on experience with Discord, Reddit, moderation bots, or automation tools.
• Experience with developer, open-source, infrastructure, networking, or security communities.
• Familiarity with Common Room or similar community engagement tools.
• Experience creating AMAs, virtual events, member spotlights, or community showcases.
• Ability to travel occasionally for community events and meetups.

Benefits

• Equity incentive plan.
• Health, vision, and dental coverage with no waiting period.
• Remote-first work and access to a corporate coworking program.
• Employer retirement contributions matched up to 0.75% of eligible compensation.
• Annual professional development allowance of $1,500 USD.
• Flexible paid time off.
• Company laptop, monthly home internet reimbursement, and $500 USD home office setup allowance.
• Paid parental leave: 20 weeks for birthing parents and 16 weeks for non-birthing parents.