New Business Account Executive, Tailscale

CA$167.5-201k

OTE

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

Salesforce

Junior and Mid level

Toronto

Vancouver

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

CA$167.5-201k

OTE

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

Salesforce

Junior and Mid level

Toronto

Vancouver

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

1+ years of prospecting or 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
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

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
Right now, we have 3 people in this role, so this is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales
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 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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