Mid-Market Account Executive

About Tailscale

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, like it used to be.

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

You will be responsible for helping expand and renew current customer accounts as well as work net-new customer accounts across inbound leads and outbound prospecting. This is a new segment and you will be involved in key groundwork in making this a repeatable and successful motion for Tailscale’s ambitious growth goals. You will be expected to own deals end-to-end; working with marketing, product, solutions engineering, and our leadership team to close key logos and drive revenue growth.

• Own an incremental revenue number each quarter while consistently building pipeline throughout the whole year.
• Ensure our existing customers get value out of Tailscale and renew + expand their usage.
• Provide accurate weekly forecasting & revenue delivery.
• Demonstrate the ability to outbound to net-new customers and generate net-new pipeline.
• You own the relationship with customers long term and sell new products as we build them.
• Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement.

• 3+ years of closing experience in an AE or AM role. Outbound experience strongly preferred.
• Has sold developer and/or technical products, especially in a product‑led growth (PLG) motion.
• Comfortable selling to senior leaders - CTO, CISO, VP of engineering, head of IT.
• Experience using Gong, Salesforce, or similar, to collaborate internally and manage pipeline.
• Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients.
• Proactive from lead to close. If this opportunity really excites you, please don’t just apply on the website. Prospect thoughtfully and tell us why you’re the best candidate for this position.
• Willing to come into our downtown Denver office 2-3 days per week #LI-Hybrid.

• Past experience selling or managing accounts with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO).
• You’ve been the owner of several customers in the $20k-100k+ ARR range previously, with evidence of growing them through expansion and cross‑sell rather than just renewal.
• Desire and ability to leverage AI to increase productivity.

US Pay Range (OTE): $200,000 – $200,000 USD.

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package including base salary, equity incentive plan and variable commission.
• Comprehensive group benefits with no waiting period for health, vision, dental and more for you and your family.
• Remote first company. Most teams work fully remotely, with optional in‑office collaboration when needed.
• Opportunities to connect with other Tail scalars in person at annual retreats, off‑sites and distributed collaboration events.
• Support for your personal and professional development, including annual $1500 USD for professional development and mentorship, coaching and promotion opportunities.
• Paid time off and healthy work‑life integration.
• Build‑your‑own home office setup: choose company‑owned laptop (Mac or PC), receive monthly home internet reimbursement, and $1000 USD to customize workstation.
• Generous parental leave program from your first day.

Tailscale is an equal opportunity employer and is committed to providing an accessible and inclusive hiring process. We encourage applications from historically marginalized groups; qualifying candidates who meet 100% of the qualifications are encouraged to apply.