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About Tailscale

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. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

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.

Tailscale is a multi-product secure connectivity platform spanning networking, privileged access, workload connectivity, and AI infrastructure. We have an opportunity to help define the future of secure connectivity, establishing Tailscale as the obvious and best networking choice for AI and agentic infrastructure. We're looking for someone who can turn our technical innovation, customer impact, and vision into compelling stories that earn attention and establish Tailscale as a category leader.

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. You'll also partner closely with a separate dedicated CEO and policy communications leader to ensure our stories are coordinated and consistent.

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. You will work directly with leaders across Product, Engineering, Marketing, People, Legal, and the executive team to build a communications function that can scale with Tailscale's ambitions.

Key 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. This should include sustained product storytelling between launches, including through independent reviews, technical publications, comparisons, creators, and third party validation. It could also include research-led PR.
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, including speaking opportunities, media engagements, and executive social presence. Partner closely with the dedicated CEO and policy communications lead to coordinate company narratives, major announcements, and executive engagement, building comms campaigns for executives that align with the overall company narrative.
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 to protect customer trust and company reputation. You should be able to improve processes over time as we scale.
Own Tailscale's awards and recognition strategy, identifying and securing high-value industry and company accolades.
Hire, manage, and develop a high-performing communications team while overseeing external agencies, communications processes, and performance measurement. This team will start small (likely 2 heads), but has the potential to grow in the future as we scale.
Partner closely with the dedicated CEO and policy communications individual contributor to maintain consistent narratives and support broader policy communications initiatives.

What We Are Looking For

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.
A hands-on, creative, and highly accountable leader who thrives in ambiguity, moves quickly, and is comfortable building from the ground up.

Nice to Have

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.
Experience collaborating with teams who support analyst relations, public policy, or major industry research initiatives.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. 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

What We Offer

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).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

CAN Pay Range 254600 - 317580 CAD

Tailscale

Head of Communications

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Tailscale

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