Manager of Commercial Sales, Tailscale
CA$268-335k
OTE
+ Equity
More information about location
3 days a week in office
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
CA$268-335k
OTE
+ Equity
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
- We are looking for someone who is excited to lead sellers on either team
- If you are looking for an opportunity to lead from the front and to build a repeatable sales machine from the ground up, this is it
- 2+ years of sales management experience in a B2B SaaS/Software company
- Aptitude for delivering world-class customer experiences: operate with a sense of urgency, exercise curiosity about customers, and strive to add value in your interactions
- Excellent written and verbal communication skills
- Ability to manage many activities and tasks simultaneously
- Ability to travel to industry events once a quarter
What the job involves
- We are looking for a gritty, thoughtful, and curious Sales Manager to lead a sales team focused on the Commercial segment (<2,000 employees)
- The Commercial team provides no shortage of fun challenges, such as a high velocity sales motion (7 to 13 opportunities per month) and occasional large opportunities ($50,000-$100,000+ ACV contracts)
- The Commercial Sales team is made up of a New Business team and an Account Management team
- Become an expert in how Tailscale helps our customers
- Lead a team of account executives from the front - prospecting with the team, leading role plays, unblocking critical opportunities, and traveling to customers to build relationships
- Establish and refine best practices for pipeline generation, opportunity management, and customer relationship building
- Develop and coach the team using sales data, performance metrics, and sales enablement
- Work closely with marketing, product, sales engineering, and partnership teams to create pipeline and accelerate opportunities
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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