Head of Communications

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. Founded in 2019 and fully distributed, backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

We are seeking a strategic, creative, and highly experienced Head of Communications to lead and scale Tailscale's global communications function. This leader will shape how Tailscale is understood by the market, elevate our visibility in the media, and build the communications engine needed to support our next phase of growth. Reporting to the SVP of Marketing, you will own product and corporate communications, public relations, media strategy, internal communications, crisis communications, award applications, international comms and media relations, new media engagement, and executive communications across the leadership team outside the CEO. This is a builder role for someone who combines strong strategic judgment with exceptional execution. You will initially be hands-on while hiring and developing a small, high-performing team.

• Develop and execute Tailscale's global communications strategy, strengthening brand awareness, reputation, and market leadership.
• Lead product and technology communications, translating complex innovations, product launches, and customer stories into compelling narratives that earn meaningful media coverage.
• Build strong relationships with top-tier business, technology, cybersecurity, and AI journalists, driving proactive media opportunities and increasing Tailscale's share of voice.
• Expand Tailscale's presence across emerging media channels, including influential podcasts, newsletters, creators, and technical communities.
• Own corporate communications for major company milestones, strategic partnerships, funding announcements, and other business developments.
• Build and scale international communications programs, including regional media relations and agency partnerships.
• Develop executive communications and thought leadership programs for the leadership team outside the CEO.
• Partner closely with the dedicated CEO and policy communications lead to coordinate company narratives.
• Oversee internal communications, partnering with People and executive leadership on company-wide messaging, all-hands, organizational changes, and employee engagement communications.
• Lead crisis communications, establishing response plans and partnering with Legal, Security, Engineering, and leadership.
• Own Tailscale's awards and recognition strategy.
• Hire, manage, and develop a high-performing communications team while overseeing external agencies, communications processes, and performance measurement.

• 10+ years of experience in public relations, product communications, or corporate communications, ideally within high-growth B2B technology companies.
• Proven track record of securing meaningful earned media coverage and building strong relationships with influential journalists.
• Deep product communications expertise, with the ability to translate complex technical products into clear, compelling stories.
• Experience hiring, managing, and developing communications professionals and overseeing agency partners.
• Exceptional writing, storytelling, and editorial judgment across external, executive, and internal communications.
• Experience advising senior executives and navigating high-stakes or sensitive communications situations.
• Strong strategic judgment and operational discipline, with the ability to prioritize, build scalable processes, and measure impact.
• Curiosity around and openness to leveraging AI to support operations and execution but not replace human taste and judgement.

• Experience in networking, cybersecurity, infrastructure, developer tools, or AI.
• Experience scaling communications at a high-growth, global technology company.
• Experience supporting fundraising, acquisitions, or pre-IPO communications as well as experience supporting a company through an IPO.

Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Range: $254,600—$317,580 CAD

Benefits include: an inclusive, flexible environment; competitive total compensation package including base salary, equity incentive plan and variable commission (for quota-based roles); comprehensive group benefits with no waiting period covering health, vision, dental, and more; remote first company; employer-funded retirement contributions with dollar-for-dollar match up to 0.75% of eligible compensation; annual company retreat and team off-sites; $1500 USD annually for professional development; flexible paid time off; build-your-own home office setup with company-owned laptop, monthly home internet reimbursement, and $500 USD workstation customization; paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents).

If this job description resonates with you, please apply via the job posting.