On-site
SaaS
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About this role
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About Tailscale
Tailscale is making safe connection effortless 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. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.
About the Role
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 an Enterprise Account Executive, you will be responsible for helping some of our largest clients and prospects to evaluate, purchase, and expand their usage of Tailscale as a solution to their company’s evolving networking, security, and compliance objectives.
You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.
We’re an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers’ needs. We are one of the fastest-growing VC-backed Dev Tool companies and are looking for folks to help us get to our next stage of growth.
You will join a team helping define the future of secure connectivity and modern networking. Tailscale’s product-led growth has created significant enterprise demand from organ
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Prospecting
Channel / Partner
Sell through partners, resellers, or alliances
Buyer Persona
Individual / End-User
Bottom-up adoption, user-level selling
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAs an Account Executive with Tailscale, you'll own the entire revenue pipeline and be measured on quota attainment.
Expect to work with recurring revenue models where customer retention is as important as acquisition.
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