New Business Account Executive

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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

We are looking for ambitious sellers to join our New Business Account Executive team. This is not a “farmer” role. You will be assigned inbound leads via round robin, however you will also be responsible for prospecting and sourcing a third of your own pipeline. You’ll own the sales cycle from prospect to purchase, and work to earn customer trust every step of the way.

Tailscale has a vibrant community across Hacker News, X, and Reddit. We have 100,000+ monthly active users, many of whom are engineering leaders working at the most innovative companies in the world. This is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales.

Responsibilities

• Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale.
• Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns.
• Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers.
• Support customers across all time zones.
• Manage and organize your activities, pipeline, and forecast in Gong and Salesforce.

Requirements

• 1+ years of prospecting or closing experience in a door-to-door or in-person sales role.
• Ambition to build (and not just follow) a sales playbook.
• A technical background or curiosity in technology.
• Excellent communication and presentation skills.
• Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.
• Experience self-sourcing opportunities, multi-threading, and guiding a customer from discovery all the way through closed-won deals, with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO).

Schedule

This role is based in Denver and is hybrid required (3 days/week in-office).

Pay

The salary range displayed represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. 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.

US Pay Range (OTE) $100,000—$125,000 USD

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including a base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period (health, vision, dental, and more for you and your family).
• Remote-first company—most teams work fully remotely. Enjoy flexibility in work location, virtual and in-person social events, and access to corporate co-working spaces like WeWork.
• Employer-funded retirement contributions (dollar-for-dollar match up to 0.75% of eligible compensation).
• Annual company retreat, team off-sites, and opportunities for in-person collaboration across Canada, the United States, the United Kingdom, and Singapore.
• $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off program for any life situation.
• Build-your-own home office setup: company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents).