Full-Time

Enterprise Account Executive

Updated on 3/13/2025

Tailscale

Tailscale

51-200 employees

Secure VPN for remote resource access

Compensation Overview

CA$201k - CA$402kAnnually

+ Equity + Variable Commission

Senior, Expert

Remote in Canada

The job is fully remote but intended for candidates based in Canada.

Category
Enterprise Sales
Sales & Account Management
Required Skills
Sales
Requirements
  • 5+ years of closing experience in a sales 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 collaborating and working with a Sales Engineer on sales cycles
Responsibilities
  • Build a credible pipeline every quarter through a land-and-expand motion
  • Take ownership of the full sales cycle from lead to close
  • 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
  • Work a book that is 50% existing clients and 50% new accounts

Tailscale offers a secure networking solution through a WireGuard-based Virtual Private Network (VPN) that allows users to access remote resources like virtual machines and databases from anywhere. Its service is particularly beneficial for businesses and development teams needing to connect to private networks securely. Tailscale stands out for its simplicity, requiring minimal setup, and supports over 100 integrations, making it versatile for various tech environments. The company's goal is to provide an easy-to-use and secure way for users to manage and access their resources remotely.

Company Size

51-200

Company Stage

Series B

Total Funding

$111.9M

Headquarters

Canada

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Tailscale's zero-trust solution is easy to deploy in existing infrastructures.
  • Partnership with Mullvad expands Tailscale's global VPN server network.
  • Viral adoption among developers indicates strong product-market fit.

What critics are saying

  • Increased competition from other zero-trust startups could impact market share.
  • A critical vulnerability in the Windows client poses a security risk.
  • Cooling venture funding may limit Tailscale's expansion capital.

What makes Tailscale unique

  • Tailscale uses WireGuard's Noise protocol for trusted encryption.
  • It integrates with existing identity providers like GSuite and Office365.
  • Tailscale offers over 100 integrations, fitting into diverse tech stacks.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Flexible Work Hours

Remote Work Options

Unlimited Paid Time Off

Parental Leave

Professional Development Budget

Home Office Stipend

Phone/Internet Stipend

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

0%

2 year growth

3%
BetaKit
Jan 14th, 2025
Tailscale Hits 10,000 Paid Business Clients After Doubling Customer Base In 10 Months

Corporate VPN startup has seen rapid growth amid strong demand from AI companies

Arun Blog
Sep 3rd, 2024
SSH setup of the future

About two weeks, Tailscale announced a fantastic SSH experience as well: Tailscale SSH that allows one to establish SSH connections with devices on my tailnet without having to generate and distribute keys.

Tailscale
Sep 7th, 2023
Mullvad on Tailscale: Privately browse the web

Tailscale has partnered with Mullvad to make its global network of VPN servers available for our customers.

Tailscale
Jun 27th, 2023
Prerequisites

Tailscale recently introduced Tailscale SSH, which allows you to use Tailscale to authenticate to your devices over SSH instead of having to rely on passwords, key rotation, copying over authorized keys and more.

Benzinga
Jun 6th, 2023
Despite Quantitative Tightening, Vcs Are Investing In Devops And Ai Security

DevOps shifts security left. “Architecture and development shifts create new opportunities for security,” says James Green, General Partner at CRV and a Forbes’ 30 under 30 honoree in 2022. The startups best positioned to land funding are those with defensible moats that usually go in hand with solving tough problems others haven’t addressed. One example is integrating security with DevOps, which empowers developers to prioritize security issues and expedite remediation. “Existing Source Code Analysis solutions are not sufficient,” Green notes. CRV’s investments in Project Discovery and Tailscale put security in the hands of developers, reducing silos and remediation time.The result of this cloudification of work is a diverse landscape of cybersecurity offerings extending protection from on-premises basics to newer terrain - developer and firmware environments, and even AI algorithms