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    Senior Customer Account Executive

    Tailscale

    Remote
    Remote
    SaaS
    Hybrid
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    Posted Today
    Work Type

    Remote

    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 a Sr. 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’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.

    Key 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 Tailsc

    Selling Motion

    Prospecting

    Channel / Partner

    Sell through partners, resellers, or alliances

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Requirements at a Glance

    Bachelor's Degree·Required

    Typical Day — Account Executive

    Demos4–6/week
    Client meetings3–5/week
    Proposals2–3/week
    Pipeline review1–2×/week

    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
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    Account Executives are the revenue engine of any sales organization — this role will require strong pipeline management and closing skills.

    Top SaaS reps often earn significant upside through accelerators once quota is exceeded.

    Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.

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