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Salary: CAD 167,500 - 167,500 / annual
Tailscale is a secure networking platform built on WireGuard that helps teams safely interconnect people and devices. The company is fully distributed, founded in 2019, and backed by top-tier VCs including Accel, CRV, and Insight.
As a Customer Account Executive, you will drive expansion and renewal of existing customer accounts within Tailscale's rapidly growing sales organization. Your primary focus will be identifying additional use cases within your book of business, educating customers on new feature releases, and ensuring successful product adoption across all assigned accounts.
Key responsibilities include:
- Become an expert in Tailscale's value proposition and how it solves customer problems
- Build a credible quarterly pipeline by engaging existing clients on upsells and renewals
- Own specific upsell and renewal revenue targets across your account portfolio
- Educate customers on Tailscale's value throughout evaluation and adoption cycles
- Balance short-term results with annual pipeline coverage and forecasting accuracy
- Create mutual action and success plans with prospects and existing customers
- Participate in video-recorded customer meetings for training, collaboration, and quality improvement
- Partner closely with Solutions Engineering, Customer Success, Support, Marketing, and Product teams
The role is based in Vancouver and requires hybrid presence (3 days per week in-office). Tailscale offers a competitive total compensation package including base salary, equity, and comprehensive benefits. The company emphasizes an inclusive, flexible environment with remote-first culture, professional development support ($1,500 USD annually), paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing), and employer-matched retirement contributions up to 0.75% of eligible compensation.
REQUIREMENTS:
- Up to 1 year of quota-carrying or closing experience in an Account Executive or Account Manager role
- Demonstrated experience selling developer and/or technical products, particularly in product-led growth (PLG) motions
- Experience presenting to senior managers and executives
- Ability to manage multiple opportunities simultaneously at various stages with a strong track record of meeting and exceeding quota
- Experience using Gong or similar tools for internal collaboration and pipeline management
- Experience partnering with Sales Engineering, support, and customer success teams
- Strong desire to join a high-growth software startup
- Proactive approach: candidates are encouraged to go beyond standard application and directly prospect the hiring manager
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
