Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be.

Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space. As a Senior Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts.

You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs. 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. Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product.



Participation in video-recorded customer meetings is a core part of this role.

Recordings are used for training, collaboration, and quality improvement. A strong desire to join a high-growth software startup ~ 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 ~ This role is based in Toronto and is hybrid preferred (3 days/week in-office). #Tailscale's compensation package includes base salary, equity, and comprehensive perks. The salary range displayed on each job posting represents the target range for a new hire's base salary.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets. 201,000 - $201,000 CAD We encourage you to help us break that statistic! An inclusive, flexible environment where you can be your authentic self. This includes a base salary,



an equity incentive plan and variable commission (for quota-based roles).

Take advantage of coverage for health, vision, dental, and more for you and your family! Remote first company -most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you).

Some roles require in-office collaboration depending on team needs, which will be clearly noted in the . Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.

Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development.

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. Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates.

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