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    Enterprise Account Executive

    Tailscale

    Remote
    SaaS
    Hybrid
    See your match score
    Posted Today
    Work Type

    On-site

    Vertical

    SaaS

    Source

    jobscollider

    About this role

    Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the

    qualifications. We encourage you to help us break that statistic!

    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

    Bachelor's Degree·Required

    Typical Day — Account Executive

    Stakeholder meetings3–5/week
    Executive presentations2–3/week
    Business cases & RFPs1–2/week
    Forecast & pipeline2×/week
    Champion coachingDaily

    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

    ARR / MRRNet Revenue Retention (NRR)CAC Payback PeriodLogo Churn vs Revenue ChurnACV (Avg Contract Value)Magic Number

    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

    sales
    —

    Walk me through your discovery process.

    Template question
    —

    How do you handle a prospect who goes silent mid-deal?

    Template question
    —

    Tell me about your largest closed deal and the sales cycle.

    Template question
    —

    How do you build business cases for stakeholders?

    Template question
    —

    Describe a deal you lost and what you learned.

    Template question
    Research Tailscale's product, recent news, and key competitors
    Prepare metrics: quota attainment %, average deal size, win rate
    Practice a 2-minute product demo pitch for a mock discovery call
    Review the job description and map your experience to each requirement
    Role Insights

    As 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.

    Are you a closer?

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