Remote opportunity at
TailscaleCommunity Engagement and Advocacy Manager
Tailscale, a company established in 2019 that builds software for secure device interconnection across teams of all sizes, is hiring a Community Engagement and Advocacy Manager…
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About This Role
Tailscale, a company established in 2019 that builds software for secure device interconnection across teams of all sizes, is hiring a Community Engagement and Advocacy Manager . This fully distributed organization is backed by several investors including Accel, CRV, Insight, Heavybit, and Uncork Capital. The person in this role will guide three fundamental community areas: the Tailscale Insiders advocacy initiative, digital spaces on Discord and Reddit, and the Community Projects…
Job Description
Tailscale, a company established in 2019 that builds software for secure device interconnection across teams of all sizes, is hiring a Community Engagement and Advocacy Manager. This fully distributed organization is backed by several investors including Accel, CRV, Insight, Heavybit, and Uncork Capital. The person in this role will guide three fundamental community areas: the Tailscale Insiders advocacy initiative, digital spaces on Discord and Reddit, and the Community Projects program.
The successful candidate will manage daily operations, establish recurring engagement opportunities, build relationships with advocates, and cultivate spaces that allow community members to connect and share expertise. Responsibilities include coordinating with internal teams such as Developer Relations, Product, Engineering, Marketing, and Support to align community projects with company initiatives. This position suits an individual who enjoys interpersonal collaboration, possesses strong organizational capabilities, and feels curious about technology.
Responsibilities
- Manage the strategy, day-to-day operations, growth, and recruitment for the Tailscale Insiders advocacy program
- Establish engagement opportunities that connect Insiders with each other and with internal departments
- Identify and nurture emerging advocates and coordinate member feedback to improve the program
- Oversee strategy, engagement, moderation, and events across Tailscale's Discord and Reddit channels
- Plan community engagement around product launches, announcements, and corporate initiatives in partnership with marketing and product groups
- Handle community moderation duties, enforce guidelines, manage bots, and coordinate volunteer moderators
- Run the Community Projects program by creating repeatable processes for discovering and showcasing user-built projects
- Partner with technical and marketing teams to turn community builds into technical content, documentation, and demos
Requirements
- Accumulate three to five or more years of background in community management, advocacy, community programs, or developer communities
- Demonstrate experience owning and growing community initiatives, coordinating stakeholders, and driving engagement
- Show a proven capability to build relationships with community members, contributors, and internal staff
- Possess experience managing and moderating online environments with established guidelines and moderation tools
- Exhibit strong written and verbal communication skills for cross-team collaboration
- Display strong organizational and program management abilities to handle multiple priorities independently
Qualifications
- Experience managing advocacy, ambassador, champion, or contributor recognition programs
- Hands-on experience handling Discord, Reddit, or similar platforms along with moderation bots
- Background working alongside developers, open source, infrastructure, networking, or security communities
- Familiarity with engagement and intelligence tools like Common Room
- Experience organizing programming such as virtual events, AMAs, and member spotlights
- Background highlighting community stories, achievements, and contributor projects
- Previous collaboration with engineering, product, support, or marketing departments
- Willingness to travel occasionally for meetups and community events
Core Skills
Benefits
- Base salary ranging from CAD 192,960 to 237,180 per year
- Equity incentive plan
- Comprehensive group health, vision, and dental benefits with no waiting period
- Employer-funded retirement contributions matching up to 0.75 percent of eligible compensation
- Flexible paid time off program
- Annual professional development allowance of USD 1,500
- Monthly home internet reimbursement and USD 500 home workstation customization fund
- Paid parental leave program offering up to 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Access to corporate co-working spaces near you
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary for the Community Engagement and Advocacy Manager role?
The target base salary range for this position is CAD 192,960 to 237,180 per year, with individual offers varying based on experience and skill set.
Is this position remote?
Yes, Tailscale operates as a remote-first company, and most teams work fully remotely.
What experience is required for this position?
Candidates must have three to five or more years of experience in community management, advocacy, community programs, developer communities, or related roles.
What benefits does Tailscale offer?
Tailscale provides comprehensive health, vision, and dental benefits with no waiting period, an equity plan, retirement contributions matching up to 0.75 percent, a professional development budget, home internet reimbursement, and paid parental leave.
Sample Interview Questions
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