Sales Director, Tailscale
EMEA
£260-300k
OTE
A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles)
More information about location
A zero config VPN for building secure networks
Posted today
A zero config VPN for building secure networks
201-500 employees
Posted today
£260-300k
OTE
A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles)
More information about location
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- 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 the job involves
- 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
- 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
- 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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