Director of Strategic Sales, Tailscale
$350-400k
OTE
+ Equity
A zero config VPN for building secure networks
Posted today
A zero config VPN for building secure networks
201-500 employees
Posted today
$350-400k
OTE
+ Equity
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
- Founding AE at a high growth start-up
- 5+ years as the top sales rep at a high-growth technology company
- Proven success selling into organizations with 10,000+ employees
- Demonstrated ability to close complex six-, seven-, and eight-figure SaaS opportunities
- A consistent track record of building outbound pipeline and winning net-new enterprise customers
- Executive presence with the ability to engage CIOs, CISOs, CTOs, and senior business executives as trusted advisors
- Strong business acumen with experience navigating complex buying committees and long enterprise sales cycles
- Comfortable operating in ambiguity and building new processes where none exist
- Passionate about building teams, developing people, and creating scalable organizations
- Want to build something rather than inherit it
- Enjoy leading from the front instead of managing from the sidelines
- Love hunting transformational opportunities and winning competitive enterprise pursuits
- Enjoy building outbound strategies as much as closing business
- Like collaborating across Product, Engineering, Marketing, and Customer Success
- Are energized by creating playbooks that become the foundation for future growth
- Want to leave a lasting impact on how a company scales its enterprise business
What the job involves
- 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 some of the world's largest organizations. As adoption accelerates, we're investing in a Strategic Sales motion that matches the scale of our ambition. If you're excited by the opportunity to build, lead, and sell and want to define how a category-leading company wins the largest enterprises in the world, we'd love to talk
- As we continue moving up-market, we're launching a new Strategic Sales organization focused exclusively on the world's largest enterprises. We're looking for a founding Director of Strategic Sales to help build one of the most important growth initiatives at Tailscale. This is a rare opportunity to define how we engage Fortune 1000 customers, establish a new go-to-market motion, recruit an elite team, and help shape the future of Enterprise Sales at Tailscale
- This is not a traditional frontline management role
- You'll be a seller, coach, and builder, personally leading many of Tailscale's largest strategic opportunities while building a high-performing team of Strategic Account Executives focused on organizations with more than 10,000 employees
- You'll define territory strategy, build an outbound-first motion, recruit exceptional talent, establish repeatable playbooks, and create the operating cadence that becomes the blueprint for Strategic Sales at Tailscale
- Our Strategic Sales organization will operate like an elite SWAT team, small, highly collaborative, and focused on pursuing a select number of transformational customers. You'll work alongside Executive Leadership, Product, Engineering, Customer Engineering, Marketing, GTM Engineering, and Customer Success to win the company's largest opportunities
- Initially, you'll lead a team of approximately 3–5 Strategic Account Executives while continuing to personally own and close strategic opportunities. As the business grows, you'll play a central role in scaling both the team and the operating model
- This role reports directly to the Head of Sales and offers the opportunity to build a category-defining Strategic Sales organization from the ground up
- Build Tailscale's Strategic Sales organization from the ground up
- Design the operating model, territory strategy, account segmentation, and engagement approach
- Develop repeatable playbooks for winning the world's largest enterprises
- Help shape the long-term vision for Strategic Sales as the business scales
- Partner with executive leadership to influence go-to-market strategy for our largest customers
- Personally own a portfolio of Tailscale's highest-value strategic accounts
- Lead complex, multi-stakeholder sales cycles from initial engagement through expansion
- Develop trusted executive relationships with CIOs, CISOs, CTOs, Chief Architects, Infrastructure leaders, and other senior decision makers
- Serve as the executive quarterback on the company's largest strategic pursuits
- Negotiate complex commercial agreements and drive successful outcomes across technical, financial, legal, and executive stakeholders
- Recruit, hire, and develop exceptional Strategic Account Executives
- Initially lead a team of approximately 3–5 Strategic AEs, expanding the organization over time
- Coach account strategy, executive engagement, negotiation, forecasting, and deal execution
- Foster a high-performance culture built on accountability, collaboration, curiosity, and continuous learning
- Build a team recognized for winning the most competitive enterprise opportunities in the market
- Lead an outbound-first sales motion
- Personally prospect into strategic accounts and build executive relationships
- Partner with SDRs, Marketing, GTM Engineering, Customer Engineering, and Customer Success to develop account plans for our highest-value prospects
- Create scalable account planning and outbound strategies that consistently generate executive engagement and qualified pipeline
- Establish best practices for strategic prospecting, account planning, and executive alignment
- Own account planning, forecasting, pipeline health, and business planning for the Strategic segment
- Inspect deal strategy and qualification throughout the sales cycle
- Use data to improve execution, identify trends, and optimize performance
- Partner closely with Product and Engineering to provide market feedback that influences product direction
- Build the operating rhythm, metrics, and inspection processes that enable the organization to scale
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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