Enterprise Account Executive, Tailscale

CA$167.5-335k

+ equity incentive plan, and variable commission for quota-based roles

Senior level

Remote from Canada

A zero config VPN for building secure networks

Job no longer available

A zero config VPN for building secure networks

101-200 employees

B2CB2BSecurityContentSaaSAPICyber Security

Job no longer available

CA$167.5-335k

+ equity incentive plan, and variable commission for quota-based roles

Senior level

Remote from Canada

101-200 employees

B2CB2BSecurityContentSaaSAPICyber Security

Company mission

To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.

Job

Company

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

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

Top investors

81% employee growth in 12 months

Trustpilot (4.3)

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.

Share this job

View 40 more jobs at Tailscale