Community Engagement and Advocacy Manager

Remote (Canada)

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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 chance, 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 transparent 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,

📌 Community Engagement and Advocacy Manager (Canada)
🏢 Tailscale
📍 Canada