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Tailscale

Community Engagement and Advocacy Manager

Tailscale

. Own the strategy, operations, engagement, and growth of the Tailscale Insiders advocacy program .

Posted 11/6/2026full-timeRemote • Canada, United StatesMid-LevelSenior💰 CA$192,960 - CA$237,180 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in community management and advocacy, with a strong focus on building relationships and driving engagement through strategic initiatives. Proficient in moderating online communities and managing community programs while effectively collaborating with cross-functional teams.

Highest-signal resume keywords
Community ManagementEngagement StrategyProgram ManagementRelationship BuildingModeration Tools

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Community ProgramsEvent DevelopmentContent CreationFeedback GatheringMetrics Monitoring
Soft Skills
Strong CommunicationOrganizational SkillsCuriosity About Technology
Tools & Technologies
DiscordRedditModeration Tools
Industry Keywords
AdvocacyCommunity EngagementDeveloper Communities

About the role

Key responsibilities & impact
  • Own the strategy, operations, engagement, and growth of the Tailscale Insiders advocacy program
  • Build relationships with Insiders and create recurring engagement opportunities
  • Identify speaking, content, event, product feedback, testing, and other participation opportunities
  • Recruit, onboard, recognize, and engage Insiders; gather feedback and track program outcomes
  • Own engagement and community experience across Tailscale’s Discord and Reddit communities
  • Develop community events, AMAs, discussions, and member spotlights
  • Bring Tailscale staff into community conversations and lead engagement around launches and announcements
  • Moderate communities, enforce guidelines, manage tools and bots, coordinate volunteer moderators, and escalate sensitive issues
  • Monitor conversations, feedback, and metrics to inform strategy, product decisions, and program improvements
  • Own and grow the Community Projects program
  • Develop processes for discovering, reviewing, tracking, and showcasing community projects
  • Build relationships with project creators and help turn projects into content, demos, documentation, and showcases
  • Create opportunities for project creators to present their work and recognize contributors
  • Collaborate with Developer Relations, Product, Engineering, Marketing, and Support teams

Requirements

What you’ll need
  • 3–5+ years of experience in community management, advocacy, community programs, developer communities, or related roles
  • Experience owning and growing community programs, including developing initiatives, coordinating stakeholders, and driving engagement
  • Proven ability to build relationships with community members, advocates, contributors, and internal teams
  • Experience managing and moderating online communities, including community guidelines and moderation tools
  • Strong written and verbal communication skills
  • Excellent organizational and program management skills; ability to manage multiple priorities, work independently, and navigate ambiguity
  • Strong understanding of community engagement and advocacy
  • Genuine curiosity about technology and eagerness to learn Tailscale products and community
  • Willingness and ability to travel occasionally to support community events, meetups, and other initiatives

Benefits

Comp & perks
  • Inclusive, flexible work environment
  • Competitive total compensation package including equity incentive plan and variable commission for quota-based roles
  • Comprehensive health, vision, dental, and other group benefits with no waiting period for employees and families
  • Fully remote work options and flexible work arrangements
  • Virtual and in-person social events
  • Corporate co-working program
  • Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually
  • Annual company retreat and team off-sites
  • $1,500 USD annually for professional development
  • Mentorship, coaching, and internal promotion opportunities
  • Flexible paid time off
  • Company-owned laptop choice of Mac or PC
  • Monthly home internet reimbursement
  • $500 USD home workstation customization allowance
  • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
  • Recruitment accommodations available