Sales Director

About Tailscale 

Tailscale is building the new Internet 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.

Tailscale is redefining secure networking by making it simple for organizations to securely connect people, devices, and workloads anywhere in the world.

At Tailscale, we're solving one of the most fundamental challenges in modern infrastructure: secure connectivity. Our product is loved by developers, trusted by IT and security teams, and rapidly expanding within organizations of every size. As adoption accelerates, we are investing in a regional sales motion that matches the scale of our ambition across EMEA.

We are looking for a founding Sales Director, EMEA to build and lead one of Tailscale's most important growth initiatives. This is a rare opportunity to shape how a category-leading company enters and scales a major region, develops strategic customer and partner relationships, recruits an exceptional team, and creates the operating model for long-term growth.

About the Role

You will be a regional leader, seller, coach, and builder. You will own the EMEA sales strategy and lead teams across multiple customer segments, while personally helping advance the region's most important opportunities and executive relationships.

You will define regional priorities, territory and segment strategy, hiring plans, outbound and expansion motions, and the operating cadence for the business. You will also help spearhead partnerships across the region, including channel, cloud, technology, and strategic alliance relationships that can accelerate customer acquisition and expansion.

Initially, you will lead a focused team of Account Executives across multiple segments and work closely with Customer Engineering, RevOps, Marketing, GTM Engineering, and Executive Leadership. As the business grows, you will play a central role in scaling the team, developing frontline leaders, and building the regional organization.

This UK-based role reports directly to the President and offers the opportunity to build Tailscale’s EMEA sales organization from the ground up.

Key Responsibilities

Build the EMEA Business

• Lead  the current team and build the EMEA sales organization and go-to-market motion.
• Develop the regional strategy, operating model, territory design, account segmentation, and coverage plan across multiple sales segments.
• Set clear regional priorities and translate company goals into executable plans for new business, expansion, and partnerships.
• Establish repeatable playbooks that reflect the needs of customers and markets across the UK and broader EMEA region.
• Provide regional market insight that helps shape company strategy, product priorities, and investment decisions.

Lead From the Front

• Personally support and, when appropriate, lead Tailscale's highest-value and most strategic EMEA opportunities.
• Develop trusted executive relationships with CIOs, CISOs, CTOs, infrastructure leaders, security leaders, and business executives.
• Serve as the regional executive sponsor and quarterback for complex, multi-stakeholder sales cycles.
• Coach teams on discovery, qualification, account strategy, executive engagement, negotiation, and deal execution.
• Navigate technical, commercial, legal, procurement, and executive stakeholders to drive successful customer outcomes.

Lead and Scale Multiple Segments

• Lead Account Executives serving multiple customer segments, from commercial and mid-market organizations through enterprise and accounts.
• Create differentiated motions, coverage models, and performance expectations appropriate to each segment.
• Recruit, hire, onboard, and develop exceptional sales talent across the region.
• Build a high-performance culture grounded in accountability, collaboration, curiosity, customer value, and continuous learning.
• Develop future leaders and create the management structure required as the EMEA organization scales.

Build Regional Partnerships

• Help define and execute the EMEA partnership strategy alongside the Partnerships organization and Executive Leadership.
• Identify markets and customer segments where partners can accelerate awareness, pipeline creation, implementation, and expansion.
• Create clear rules of engagement, joint account plans, and co-selling motions with priority partners.
• Represent Tailscale with senior partner executives and at relevant regional customer and industry events.

Create Pipeline and Regional Awareness

• Lead an outbound-first and account-based sales motion across the region.
• Personally build executive relationships within high-priority accounts and partner ecosystems.
• Partner with SDRs, Marketing, GTM Engineering and Partnerships to create qualified pipeline.
• Build scalable account planning, prospecting, event, community, and partner-sourced pipeline programs.
• Ensure the region develops a balanced pipeline across customer segments, products, countries, and sources.

Drive Operational Excellence

• Own regional forecasting, pipeline health, hiring plans, and performance management.
• Establish a rigorous operating cadence across forecast reviews, pipeline creation, deal inspection, account planning, and talent development.
• Use data to identify trends, improve execution, allocate resources, and communicate regional performance to leadership.
• Partner closely with Product and Engineering to provide structured customer and market feedback from EMEA.
• Build the metrics, processes, and cross-functional relationships required to scale the organization effectively.

What We Are Looking For

• An experienced sales leader who has built or materially scaled a high-growth SaaS business in EMEA.
• A proven leader of teams spanning multiple customer segments, with the judgment to adapt the sales motion by segment and market.
• A builder who is comfortable operating with ambiguity, limited infrastructure, and significant ownership.
• A strong seller and coach with a consistent record of winning complex new-business and expansion opportunities.
• Experienced in recruiting, developing, and retaining high-performing Account Executives and sales leaders.
• Demonstrated success building outbound pipeline and establishing repeatable regional go-to-market motions.
• Experienced developing channel, technology, cloud, reseller, or strategic partnership relationships in EMEA.
• Executive presence and credibility with CIOs, CISOs, CTOs, and senior business leaders.
• Strong business acumen and experience navigating complex buying committees, procurement processes, and enterprise sales cycles.
• Deep familiarity with the UK and broader EMEA technology market; additional European language skills are valuable but not required.
• Based in the United Kingdom and able to travel throughout EMEA as needed.

You'll Thrive Here If You...

• Want to build a region rather than inherit a mature organization.
• Enjoy leading from the front while creating leverage through managers, teams, and partners.
• Can balance strategic planning with hands-on customer and deal leadership.
• Are energized by developing different sales motions for commercial, mid-market, enterprise, and strategic customers.
• See partnerships as a core growth lever rather than a separate or secondary function.
• Want to leave a lasting impact on how a category-leading company expands internationally.

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.

UK Pay Range

£260,000 - £300,000 GBP

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

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.