Senior New Business Account Executive - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices. From hobbyists to multinational corporations, teams of every size use Tailscale to protect their networks and share access to internal tools. Founded in 2019 and fully distributed, we are 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, but 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.

Key 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.
• Evangelize: Travel to or organize local events and attend large industry events to represent Tailscale.
• Support: Assist customers across all time zones.
• Manage: Organize your activities, pipeline, and forecast in Gong and Salesforce.

What We Are Looking For

• 2+ 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.
• Experience self-sourcing opportunities and guiding a customer from discovery through closed-won deals with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO).
• Note: This role is based in Denver and requires a hybrid schedule (3 days/week in-office).

What We Offer

• Competitive Compensation: Base salary, equity incentive plan, and variable commission.
• Comprehensive Benefits: Health, vision, and dental coverage with no waiting period.
• Retirement: Employer-funded retirement contributions (match up to 0.75% of eligible compensation).
• Professional Development: $1,500 USD annually for growth and learning.
• Work-Life Integration: Flexible PTO, paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing), and a home office setup stipend ($500).
• Connection: Annual company retreats, team off-sites, and corporate co-working program access.