Remote opportunity at
TailscaleHead of Communications
Tailscale is seeking a strategic and creative Head of Communications to lead and expand its global communications organization. Operating as a fully distributed company founded in…
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About This Role
Tailscale is seeking a strategic and creative Head of Communications to lead and expand its global communications organization. Operating as a fully distributed company founded in 2019, Tailscale develops secure connectivity software spanning networking, workload connectivity, AI infrastructure, and privileged access. Backed by investors such as Accel, CRV, and Insight, the firm aims to make network security effortless for everyone from individual hobbyists to large multinational enterprises. In this role,…
Job Description
Tailscale is seeking a strategic and creative Head of Communications to lead and expand its global communications organization. Operating as a fully distributed company founded in 2019, Tailscale develops secure connectivity software spanning networking, workload connectivity, AI infrastructure, and privileged access. Backed by investors such as Accel, CRV, and Insight, the firm aims to make network security effortless for everyone from individual hobbyists to large multinational enterprises.
In this role, you will report directly to the SVP of Marketing and take ownership of corporate communications, media strategy, public relations, crisis management, executive thought leadership, and internal messaging. The position starts as a hands-on builder role where you will establish scalable processes and manage an initial small team of approximately two heads, with opportunities for future growth. You will collaborate extensively with cross-functional partners across Engineering, Product, Legal, People, and executive leadership, while coordinating closely with a separate dedicated CEO and policy communications lead.
The ideal candidate is an accountable leader who combines strong operational discipline with excellent editorial judgment, capable of translating intricate technical innovations into compelling narratives. The compensation package for this role ranges from CAD 254,600 to CAD 317,580 per year, accompanied by equity and comprehensive employee benefits.
Responsibilities
- Design and execute a comprehensive global communications strategy to enhance brand reputation and market leadership
- Lead product and technology communications by converting technical updates and customer stories into earned media coverage
- Forge relationships with key journalists across technology, business, cybersecurity, and artificial intelligence sectors
- Grow company visibility across alternative media channels such as newsletters, podcasts, creator platforms, and technical communities
- Manage corporate communications surrounding funding rounds, business updates, and strategic partnerships
- Scale international communications efforts, which includes overseeing agency partnerships and regional media relations
- Build thought leadership programs and manage executive communications for leadership team members excluding the CEO
- Collaborate with the dedicated CEO and policy communications lead to align company narratives and executive announcements
- Direct internal communications in partnership with leadership and the People team for company-wide updates and employee engagement
- Formulate crisis response plans alongside Legal, Security, and Engineering teams to safeguard company reputation
- Identify and secure high-value industry awards and accolades
- Hire, mentor, and lead a high-performing communications team while supervising external agency partners
Requirements
- Possess at least ten years of professional experience in corporate communications, product communications, or public relations within high-growth business-to-business technology companies
- Demonstrate a proven history of earning significant media coverage and forming strong connections with prominent journalists
- Show deep expertise in product communications with the ability to articulate complex technical products clearly
- Bring experience in managing, hiring, and mentoring communications staff alongside overseeing external agency partners
- Exhibit exceptional storytelling, writing, and editorial capabilities spanning internal, external, and executive communications
- Have experience providing counsel to senior executives and managing sensitive or high-stakes communications scenarios
- Display strong operational discipline and strategic judgment to prioritize initiatives and measure impact
- Maintain curiosity and willingness to utilize artificial intelligence to support operational execution
- Demonstrate a hands-on, accountable, and creative leadership style suited for a fast-paced environment
Qualifications
- Prior experience working in infrastructure, networking, cybersecurity, developer tools, or artificial intelligence
- Background in scaling communications at a fast-growing global technology company
- Experience supporting corporate events such as acquisitions, fundraising, pre-IPO communications, or guiding a company through an initial public offering
- Familiarity collaborating with teams supporting public policy, analyst relations, or major industry research initiatives
Core Skills
Benefits
- Competitive total compensation package featuring a base salary, equity incentive plan, and comprehensive group benefits with no waiting period
- Employer-funded retirement contributions matching dollar-for-dollar up to 0.75 percent of eligible compensation
- Flexible and inclusive remote-first work environment with opportunities for co-working space access
- Annual professional development budget of 1500 USD
- Flexible paid time off program designed to support work-life integration
- Build-your-own home office setup with a company-owned Mac or PC, monthly internet reimbursement, and 500 USD for workstation customization
- Paid parental leave providing up to 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Opportunities for in-person collaboration through annual company retreats and team off-sites
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary range for the Head of Communications role?
The target base salary range for this position in Canada is CAD 254,600 to CAD 317,580 per year, supplemented by equity and comprehensive benefits.
Is this position remote?
Yes, Tailscale operates as a remote-first company where team members can work from anywhere with internet access.
Who will this position report to?
This role reports directly to the SVP of Marketing.
What kind of experience is required?
Candidates must have 10 or more years of experience in public relations, product communications, or corporate communications within high-growth B2B technology companies.
Sample Interview Questions
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