Global Head of Communications & Brand Strategy

Tailscale; Canada; Remote; CAD 255,000 - 318,000; Full time

Benefits offered by this job

Remote first company

Comprehensive group benefits

Equity incentive plan

Variable commission (quota-based roles

Employer-funded retirement

Annual company retreat

Professional development stipend

Paid time off

Home office setup

Parental leave top-ups

Job summary

Tailscale is seeking a Head of Communications to lead and scale our global communications function. You will shape market narratives, elevate media visibility, and build a scalable comms engine to support growth.

Reporting to the SVP of Marketing, you’ll own product and corporate communications, media strategy, and executive communications across leadership teams. You will hire and develop a small, high-performing team and collaborate with Product, Engineering, Marketing, People, Legal, and the

Qualifications

• 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.

Responsibilities

• 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.
• Expand presence across emerging media channels, including podcasts, newsletters, creators, and technical communities.
• Own corporate communications for major milestones, 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 leadership team outside the CEO.
• Oversee internal communications with People and executive leadership on company-wide messaging.
• Lead crisis communications, establishing response plans and improving processes as we scale.
• Own awards and recognition strategy, identifying and securing high-value industry accolades.
• Hire, manage, and develop a high-performing communications team while overseeing agencies and processes.
• Coordinate with CEO and policy comms lead to align narratives and major announcements.

Skills

Public relations

Media relations

Executive communications

Team leadership

Strategic planning

Writing skills

Job description

Tailscale is seeking a Head of Communications to lead and scale our global communications function. You will shape market narratives, elevate media visibility, and build a scalable comms engine to support growth.

Reporting to the SVP of Marketing, you’ll own product and corporate communications, media strategy, and executive communications across leadership teams. You will hire and develop a small, high-performing team and collaborate with Product, Engineering, Marketing, People, Legal, and the