← All roles

Customer Account Executive

Tailscale· Sales
Apply on company site
Hybrid (Toronto, ON)CA$167.5kfull-timePosted 2w ago

About the role

Customer Account Executive responsible for expanding and renewing existing customer accounts, educating clients on new feature releases, and ensuring adoption of Tailscale across accounts. Collaborates with Solutions Engineering, Customer Success, Support, Marketing, and Product teams in a hybrid Toronto-based role.

Responsibilities

  • Become an expert in how Tailscale helps our customers.
  • Build a credible pipeline every quarter by engaging with clients on upsells and renewals.
  • Own an upsell and renewal number across your accounts.
  • 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 where appropriate to help them evaluate and expand their usage of the Tailscale product.
  • Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement.

Qualifications

  • Up to 1 year of quota-carrying or closing experience, in an AE or an AM 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 partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients
  • Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.

Skills

Required:quota-carrying / closing experienceSales enablement tools (e.g., Gong)Solution/Enterprise-level presentingCross-functional collaborationRemote/work flexibility

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package (base salary, equity incentive plan and variable commission).
  • Comprehensive group benefits with no waiting period (health, vision, dental, etc.).
  • Remote first company with optional in-office collaboration as noted in job description.
  • Employer-funded retirement contributions (matches up to 0.75% of eligible compensation).
  • Annual company retreats and in-person team events; cross-country collaboration.
  • Professional development support ($1500 USD annually) and mentorship opportunities.
  • Paid time off with flexible, paid time off program.
  • Build-your-own home office setup (laptop, internet reimbursement, workstation stipend).
  • Paid parental leave program (20 weeks birthing parents, 16 weeks non-birthing).
Last updated Oct 8, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
Company profileWebsite

More open roles at Tailscale