Community Engagement and Advocacy Manager

Responsibilities

• 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 clear 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.
• Own the strategy, day-to-day engagement, and overall community experience across Tailscale's Discord and Reddit communities, fostering welcoming, active, and inclusive spaces.

Requirements

• 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 meaningful relationships with community members, advocates, contributors, and internal teams.
• Experience managing and moderating online communities, including community guidelines, moderation tools, and maintaining healthy, inclusive environments.
• Strong written and verbal communication skills, with the ability to engage authentically and collaborate across teams.
• Excellent organizational and program management skills, with the ability to manage multiple priorities, work independently, and navigate ambiguity.
• Strong understanding of community engagement and advocacy, with the ability to identify opportunities, recognize contributors, and turn feedback into meaningful improvements.
• Genuine curiosity about technology and an eagerness to learn about Tailscale's products and community.

Preferred

• Experience managing advocacy, ambassador, champion, or contributor recognition programs.
• Hands-on experience managing Discord, Reddit, or similar community platforms, including moderation bots and automation tools.
• Experience working with developers, open source, infrastructure, networking, security, or other technology-focused communities.
• Familiarity with community engagement and intelligence tools such as Common Room.
• Experience developing community programming such as AMAs, virtual events, member spotlights, and recurring engagement initiatives.
• Experience identifying and amplifying community stories, projects, or contributor achievements.
• Experience collaborating with Product, Developer Relations, Engineering, Marketing, or Support teams.
• Willingness and ability to travel occasionally to support community events, meetups, and other initiatives.

Benefits

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
• Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).