New Business Account Executive, Tailscale
Canada
CA$167.5-201k
OTE
+ Equity
More information about location
3 days a week in office
A zero config VPN for building secure networks
Job no longer available
A zero config VPN for building secure networks
201-500 employees
Job no longer available
CA$167.5-201k
OTE
+ Equity
More information about location
3 days a week in office
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
- 1 or more years of closing experience in a door-to-door or in-person sales role
- Ambition to build (and not just follow) a sales playbook
- A technical background or curiosity in technology
- Excellent communication and presentation skills
- Proactive from lead to close - the hiring manager for this role is Chris Chang. If this opportunity really excites you, please don’t just apply on the website. Prospect thoughtfully and tell us why you’re the best candidate for this position
What the job involves
- We are looking for ambitious sellers to join our New Business Account Executive team. This is not a “farmer” role
- You will be assigned inbound leads via round robin, however you will also be responsible for prospecting and sourcing a third of your own pipeline
- You’ll own the sales cycle from prospect to purchase, and work to earn customer trust every step of the way
- Tailscale has a vibrant community across Hacker News, X, and Reddit
- We have 100,000+ monthly active users, many of whom are engineering leaders working at the most innovative companies in the world
- This is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales
- Become an expert in how Tailscale helps our customers
- Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale
- Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns
- Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers
- Support customers across all time zones
- Manage and organize your activities, pipeline, and forecast in Gong and Salesforce
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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