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Posted Apr 15, 2026

Customer Account Executive

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Tailscale is a company focused on building the new Internet through secure software solutions. The Customer Account Executive will play a key role in expanding and renewing customer accounts while collaborating with various teams to ensure successful adoption of Tailscale's products. 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 Skills - Up to 1 year of quota-carrying or closing experience, in an AE or an AM role - A strong desire to join a high-growth software startup in a fully remote role - 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 Benefits - Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! - Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. - Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! - A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. - Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. Company Overview - Tailscale is a software company that provides zero-configuration virtual private networks (VPNs) for secure connectivity. It was founded in 2019, and is headquartered in Toronto, Ontario, CAN, with a workforce of 201-500 employees. Its website is https://www.tailscale.com.
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