Enterprise Account Executive, Tailscale
£160-200k
OTE
+ Equity
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
101-200 employees
Be an early applicant
£160-200k
OTE
+ Equity
101-200 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
- 5+ years of closing experience in a sales role
- A strong desire to join a high-growth software startup in a fully remote role
- Has sold developer and/or technical products, especially in a product-led growth (PLG) motion
- Experience presenting to senior managers and executives
- The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota
- Experience using Gong, or similar, to collaborate internally and manage pipeline
- Experience collaborating and working with a Sales Engineer on sales cycles
What the job involves
- Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space
- As an Enterprise Account Executive, you will be responsible for helping some of our largest clients and prospects to evaluate, purchase, and expand their usage of Tailscale as a solution to their company’s evolving networking, security, and compliance objectives
- You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams
- Build a credible pipeline every quarter through a land-and-expand motion
- Take ownership of the full sales cycle from lead to close
- Help educate customers on the value of Tailscale throughout the evaluation & adoption cycle
- Generate short-term results while maintaining annual pipeline coverage
- Provide accurate weekly forecasting & revenue delivery
- Create mutual action/success plans with prospective and existing customers
- Work a book that is 50% existing clients and 50% new accounts
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 plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering 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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