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Salary: CAD 167,500 - 167,500 / annual
Tailscale is a secure networking platform built on WireGuard that helps teams and organizations safely interconnect people and devices. Founded in 2019 and backed by top-tier VCs (Accel, CRV, Insight, Heavybit, Uncork Capital), the company is fully distributed and rapidly growing in the Developer Security space.
As a Customer Account Executive, you will own and expand existing customer accounts through upsells and renewals. Your primary focus will be identifying additional use cases within your book of business, educating customers on new feature releases, and ensuring successful adoption of Tailscale across all accounts. You will work closely with the Solutions Engineering team and collaborate with Customer Success, Support, Marketing, and Product teams to drive positive outcomes.
Key responsibilities include:
- Become an expert in Tailscale's value proposition and how it solves customer problems
- Build a credible pipeline each quarter by engaging existing clients on upsells and renewals
- Own specific upsell and renewal revenue targets across your accounts
- Educate customers on Tailscale's value throughout the evaluation and adoption cycle
- Generate short-term results while maintaining annual pipeline coverage
- Provide accurate weekly forecasting and revenue delivery
- Create mutual action and success plans with prospective and existing customers
- Participate in video-recorded customer meetings (recordings used for training and quality improvement)
The role is based in Toronto and requires hybrid work: 3 days per week in-office, with flexibility for remote work.
REQUIREMENTS:
- Up to 1 year of quota-carrying or closing experience in an Account Executive (AE) or Account Manager (AM) role
- Strong desire to join a high-growth software startup
- Experience selling developer and/or technical products, especially 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 to collaborate internally and manage pipeline
- Experience partnering with Sales Engineering, support, and customer success teams
- Proactive approach: the posting encourages candidates to go beyond applying on the website and directly prospect the hiring manager
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
