Mid-Market Account Executive

About

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 an 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 – the hiring manager for this role is Ben Roberts. 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

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale’s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting 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)

$200,000 – $200,000 USD

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!

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota‑based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for…