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 engagement

Build relationships with advocates, contributors, and community members

Manage Discord and Reddit engagement, moderation, and community experience

Develop events, AMAs, discussions,



spotlights, and participation opportunities

Discover, review, track, and showcase community-built projects

Requirements

3–5+ years in community management, advocacy, or related roles

Experience owning and growing community programs

Experience managing online communities and moderation tools

Strong written, verbal, organizational, and program management skills

Curiosity about technology and eagerness to learn Tailscale products

Bring community strategy, advocacy, moderation, and relationship-building expertise to Tailscale’s distributed Canadian team.

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