Head of Communications

About this role

Lead and scale Tailscale’s global communications function, shaping its market reputation and positioning it as a category leader in secure connectivity. The role spans product and corporate communications, media relations, internal and crisis communications, and executive thought leadership. It is a hands-on leadership role that begins with building and developing a small communications team.

About the company

Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.

What you'll do

• Develop and execute global communications strategy to grow brand awareness, reputation, and market leadership.
• Lead product and technology storytelling, including launches, customer stories, ongoing coverage, and research-led PR.
• Build relationships with journalists and expand presence in podcasts, newsletters, creator channels, and technical communities.
• Lead corporate communications for company milestones, partnerships, and funding announcements.
• Build international communications programs and regional agency partnerships.
• Develop executive communications and thought leadership for leaders outside the CEO.
• Oversee internal communications and lead crisis communications planning and response.
• Hire and develop the communications team, manage agencies, and measure performance.

What we're looking for

• 10+ years of experience in public relations, product communications, or corporate communications, ideally in high-growth B2B technology.
• Track record of securing meaningful earned media coverage and building journalist relationships.
• Expertise translating complex technical products into compelling stories.
• Experience managing communications professionals and agency partners.
• Exceptional writing, storytelling, and editorial judgment across external, executive, and internal communications.
• Experience advising senior executives and handling sensitive communications situations.
• Strong strategic judgment, operational discipline, and ability to build processes and measure impact.
• Hands-on, creative, accountable leadership style and comfort building from the ground up.

Nice to have

• Experience in networking, cybersecurity, infrastructure, developer tools, or AI.
• Experience scaling communications at a global technology company.
• Experience with fundraising, acquisitions, pre-IPO communications, or IPO support.
• Experience collaborating with analyst relations, public policy, or industry research teams.

Benefits

• Equity incentive plan.
• Remote-first work and corporate coworking program.
• Employer retirement contributions matched up to 0.75% of eligible compensation.
• Flexible paid time off.
• Annual professional development budget of $1,500.
• Home office setup allowance of $500 and monthly internet reimbursement.
• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.
• Health, vision, and dental coverage with no waiting period.