Customer Account Executive, Tailscale
Canada
CA$167.5-201k
OTE
+ Equity incentive plan & variable commission
More information about location
3 days a week in office
A zero config VPN for building secure networks
Open for applications
A zero config VPN for building secure networks
101-200 employees
Open for applications
CA$167.5-201k
OTE
+ Equity incentive plan & variable commission
More information about location
3 days a week in office
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
- 2+ years of closing experience in an AE or an AM 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 partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients
- Must be located in Vancouver or Toronto to be considered. The team coworks at a WeWork 3 days a week (Tu-Thurs)
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 a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts
- You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts
- You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams
- We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs
- Build a credible pipeline every quarter by engaging with clients on upsells and renewals
- Own an upsell and renewal number across your accounts
- 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 where appropriate to help them evaluate and expand their usage of the Tailscale product
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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