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Salary: USD 150,000 - 190,000 / 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 Senior Customer Account Executive, you will drive expansion and renewal revenue across an existing customer portfolio. Your primary focus is identifying additional use cases within current accounts, educating customers on new feature releases, and ensuring successful adoption of Tailscale. You will own specific upsell and renewal targets and work closely with Solutions Engineering, Customer Success, Support, Marketing, and Product teams to maximize customer value.
Key responsibilities include:
- Become a product expert on how Tailscale solves customer problems
- Build a credible quarterly pipeline through strategic customer engagement on upsells and renewals
- Own specific upsell and renewal revenue targets
- 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 prospects and existing customers
- Participate in video-recorded customer meetings for training, collaboration, and quality improvement
This is a hybrid role based in San Francisco requiring 3 days per week in-office. The company emphasizes proactive outreach—they encourage candidates to go beyond the standard application and directly engage with the hiring manager to demonstrate genuine interest.
Tailscale offers a remote-first culture with intentional in-person connection through annual retreats and team off-sites. The company maintains flexible, paid time off, comprehensive benefits with no waiting period, employer-matched retirement contributions (up to 0.75% of eligible compensation), $1,500 USD annually for professional development, a build-your-own home office setup, and paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing parents).
REQUIREMENTS:
- 2+ years of closing experience in an Account Executive (AE) or Account Manager (AM) role
- Strong desire to join a high-growth software startup
- Demonstrated 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 to drive positive client outcomes
- Based in San Francisco with ability to work hybrid (3 days/week in-office)
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
