Shape Tailscale community programs remotely across Canada through advocacy, digital communities, and relationship building. Connect contributors with meaningful participation opportunities.As Community Engagement and Advocacy Manager, you will own the Tailscale Insiders program, Discord and Reddit communities, and Community Projects. You will create opportunities for members to connect, contribute, share expertise, and gain recognition.

Success requires solid communication, organization, moderation, and program management skills.Key Responsibilities:

Own Insiders strategy, operations, recruitment, onboarding, and ongoing engagementBuild relationships with advocates, contributors, and community membersManage Discord and Reddit engagement, moderation, and community experienceDevelop events, AMAs, discussions,



spotlights, and participation opportunitiesDiscover, review, track, and showcase community-built projectsRequirements:

3–5+ years in community management, advocacy, or related rolesExperience owning and growing community programsExperience managing online communities and moderation toolsStrong written, verbal, organizational, and program management skillsCuriosity about technology and eagerness to learn Tailscale productsBring community strategy, advocacy, moderation, and relationship-building expertise to Tailscale’s distributed Canadian team.

📌 Community Advocacy Program Manager (Winnipeg)
🏢 Tailscale
📍 Winnipeg