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Salary: CAD 201,000 - 201,000 / annual
Tailscale is a secure networking platform built on WireGuard that makes it easy to securely interconnect people and their devices. Founded in 2019 and backed by top-tier VCs (Accel, CRV, Insight, Heavybit, Uncork Capital), the company is rapidly growing in the Developer Security space.
As a Senior Customer Account Executive, you will drive expansion and renewal of existing customer accounts. 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 assigned accounts. You will work closely with the Solutions Engineering team and collaborate with Customer Success, Support, Marketing, and Product teams to maximize customer outcomes.
Key responsibilities include:
- Become a product expert on how Tailscale solves customer problems
- Build a credible pipeline each quarter through upsell and renewal engagement
- 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
- Provide accurate weekly forecasting and revenue delivery
- Create mutual action and success plans with customers to help them expand usage
- 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).
REQUIREMENTS:
- 2+ years of closing experience in an Account Executive or Account Manager role
- Strong desire to join a high-growth software startup
- Proven 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 for internal collaboration and pipeline management
- Experience partnering with Sales Engineering, support, and customer success teams
- Proactive approach: the posting encourages candidates to go beyond standard application and directly prospect the hiring manager to demonstrate fit
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
