Manager of Commercial Sales, Tailscale

$200-250k

OTE

OTE range is inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets. + Equity

Senior and Expert level

Denver

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

B2CB2BSecurityContentSaaSAPICyber Security

Open for applications

$200-250k

OTE

OTE range is inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets. + Equity

Senior and Expert level

Denver

More information about location

3 days a week in office

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

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

Top investors

81% employee growth in 12 months

Trustpilot (4.1)

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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