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Senior Customer Account Executive

Tailscale· Sales
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Hybrid (Toronto, ON)CA$201kfull-timePosted 4d ago

About the role

Senior Customer Account Executive responsible for expanding and renewing current customer accounts, educating clients on new features, and driving adoption of Tailscale across existing accounts 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

  • 2+ years of closing experience in an AE or an AM role
  • A strong desire to join a high-growth software startup
  • 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:Account management / upsellSales forecastingPipeline managementExecutive communicationCross-functional collaboration

Benefits

  • An inclusive, flexible environment where you can be your authentic self
  • A competitive total compensation package (base salary, equity, and variable commission)
  • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
  • Remote first company with optional in-office collaboration depending on team needs
  • Employer-funded retirement contributions (match up to 0.75% of eligible compensation)
  • Annual company retreat and team off-sites
  • Support for personal and professional development ($1500 USD annually)
  • Paid time off and flexible PTO
  • Build-your-own home office setup (laptop, home internet reimbursement, $500 USD to customize workstation)
  • Paid parental leave program (20 weeks birthing, 16 weeks non-birthing)
Last updated Oct 22, 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

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