Mid-Market Account Executive

Tailscale · Hybrid (Denver, Colorado, United States)

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Sales / BD Hybrid (Denver) Posted May 27, 2026 200,000 – 200,000 USD

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.

Job Description

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.

Key Responsibilities

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.

What We Are Looking For

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

Nice to Have

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!

What We Offer

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 health, vision, dental, and more for you and your family!
Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

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