---
title: 'Enterprise Account Executive at Tailscale'
canonical: 'https://feeny.ai/job/enterprise-account-executive-tailscale-san-francisco-3a6j3dh22xzp'
type: 'job'
last_seen: '2026-10-13'
---

# Enterprise Account Executive at Tailscale

- **Company:** Tailscale
- **Location:** San Francisco, CA
- **Compensation:** $250k–$300k
- **Work type:** remote
- **Posted:** 2026-09-28
- **Last confirmed live:** 2026-10-13
- **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4738677005

## Job description

Thank you for considering Tailscale. If this job description resonates with you, please apply. 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!

## About Tailscale

Tailscale is making safe connection effortless 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.

## About the Role

Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.

As an Enterprise Account Executive, you will be responsible for helping some of our largest clients and prospects to evaluate, purchase, and expand their usage of Tailscale as a solution to their company’s evolving networking, security, and compliance objectives. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.

We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs. We are one of the fastest-growing VC-backed Dev Tool companies and are looking for folks to help us get to our next stage of growth. You will join a team helping define the future of secure connectivity and modern networking. Tailscale's product-led growth has created significant enterprise demand from organizations looking to simplify network access, strengthen security, and accelerate developer productivity. As an Enterprise Account Executive, you will work with some of the world's most sophisticated technology organizations to help them modernize legacy networking and security infrastructure.

We are looking for enterprise sellers who know how to create opportunities, not just manage them. You are comfortable building executive relationships, navigating complex organizations, and earning credibility with both technical and business stakeholders. You understand how to translate technical capabilities into measurable business outcomes and can lead customers through transformational technology decisions.

## Key Responsibilities

- Own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities
- Proactively self-source pipeline through outbound prospecting activities, including cold outreach, strategic account targeting and networking.
- Take ownership of the full sales cycle from lead to close
- Develop strategic account plans that identify key stakeholders, organizational priorities, technical initiatives, and expansion paths across the account
- Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders to drive alignment and consensus throughout the buying process
- Navigate complex enterprise sales cycles involving multiple decision-makers, procurement processes, security reviews, and legal negotiations
- Position Tailscale as a strategic platform for secure connectivity and modern network access by helping customers understand both the technical and business value of the solution
- Lead cross-functional account teams consisting of Sales Engineering, Customer Success, Product, Marketing, and Support to deliver exceptional customer outcomes
- Drive adoption beyond the initial deployment by identifying opportunities for broader organizational usage and long-term account growth

## What We Are Looking For

- 5+ years of closing experience in a sales role
- Demonstrated success selling infrastructure, networking, cybersecurity, cloud, developer tools, or other highly technical software solutions
- Proven track record of consistently meeting or exceeding quota in an enterprise sales environment
- Experience managing complex, multi-stakeholder sales processes involving technical and executive buyers
- Ability to engage credibly with both technical practitioners and senior business leaders
- Experience collaborating and working with a Sales Engineer on sales cycles
- Strong account planning, discovery, and business case development skills
- Experience closing six-figure enterprise opportunities is strongly preferred
- Experience using Gong, or similar, to collaborate internally and manage pipeline
- Location: Remote, but based in or near San Francisco as it supports customers and requires occasional travel/commute within the assigned region.

What Success Looks Like

- Consistently exceed quota through a combination of self-generated pipeline, new customer acquisition, and account expansion
- Establish trusted advisor relationships with Security, Infrastructure, and Engineering leaders
- Successfully drive adoption from initial deployment to broader organizational standardization
- Build a predictable pipeline through disciplined prospecting and strategic account development

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) $250,000—$300,000 USD

## 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.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- 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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

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.

## About Tailscale

## Company Overview
- **One-liner**: Tailscale provides a zero-trust identity-based connectivity platform that replaces legacy VPNs, SASE, and PAM to securely connect remote teams, multi-cloud environments, CI/CD pipelines, edge/IoT devices, and AI workloads.
- **Entity Type**: Private (Series B)
- **Headquarters**: Toronto, Canada (fully remote, with team members also in the United States and United Kingdom)
- **Founded**: 2019
- **Founders**: Avery Pennarun (CEO), David Carney (Chief Strategy Officer), and Brad Fitzpatrick (creator of LiveJournal, Memcached, and OpenID)

## Core Business
- **Primary industry/industries**: Secure connectivity, zero-trust networking, VPN replacement, infrastructure security
- **Target customers**: B2B – from small businesses and open-source projects to mid-market and enterprise organizations (30,000+ businesses use Tailscale). Also serves developers, IT teams, and DevOps engineers.
- **Mission or purpose statement**: “We want to help everyone create their own secure networks built around people and their connections. By making connectivity easier and more secure, we empower teams to build systems that scale, without scaling overhead.”

## Products & Services
- **Tailscale (Core Platform)** – A zero-trust mesh overlay network that provides identity-based access to any resource (servers, containers, SaaS tools, cloud instances) without public exposure. Replaces legacy VPNs, bastion hosts, and complex firewall rules. Includes features like SSH, Kubernetes access, database connectivity, and Aperture for securing AI workloads.
- **Tailscale Funnel** – Expose local services to the internet securely through Tailscale’s infrastructure.
- **Tailscale Serve** – Allow specific devices on a tailnet to serve content publicly or privately.
- **Tailscale SSH** – Manage SSH access with identity-based, auditable controls.
- **Tailscale Aperture** – Secure access for AI/ML workloads and data pipelines.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company)
- **Key Metric (Funding)**: Total funding of approximately $105M across multiple rounds. Series A ($35M) led by CRV in 2021; Series B ($70M) led by Accel and Insight Partners in 2022.
- **Key Metric (Customers)**: 30,000+ businesses use Tailscale. Headcount estimated at ~290 employees as of 2026.
- **Notable Investors/Partners**: Accel, CRV, Insight Partners, Heavybit, Uncork Capital. Investors include Amit Kumar (Partner at Accel), Reid Christian (Partner at CRV), Joseph Ruscio (Partner at Heavybit), Rebecca Liu-Doyle (Director at Insight Partners), and Andy McLoughlin (Partner at Uncork).
- **Growth Signals**: 25x headcount growth without dedicated IT resources for onboarding; 90% reduction in internal support requests; thousands of hours saved with fewer connectivity issues. Strong adoption in the AI era for securing workloads.

## Competitive Advantages
- **Built on WireGuard**: Tailscale is built on the modern, audited, and high-performance WireGuard protocol (wireguard-go), with upstream contributions to the open-source project.
- **Zero Trust by Design**: Identity-based access, end-to-end encryption, point-to-point connections (no central VPN server to bottleneck or inspect traffic). User privacy is a fundamental design principle.
- **Simplicity & Speed**: “It has to just work” – installation takes minutes, configuration is minimal, and the platform is cross-platform and infrastructure-agnostic.
- **Open Source Core**: The core client and server code are open source, and Tailscale offers a free plan for open-source projects, building trust and community.
- **Small, Excellent Teams**: The company philosophy is “small is beautiful” – they believe small, excellent teams produce coherent, high-quality outcomes that large teams cannot replicate.

## Strategic Focus
- **AI & Multi-Cloud Connectivity**: Tailscale is positioning itself as the secure connectivity platform for the AI era, with specific features (Aperture) for AI workloads.
- **Expanding Enterprise Features**: Adding capabilities like Privileged Access Management (SSH, K8s, databases), granular access controls, and audit logging.
- **Scaling the Business**: With 30,000+ businesses already onboard, the focus is on converting free/open-source users to paid plans and expanding into larger enterprise accounts.
- **Global Hiring**: Actively hiring across engineering (Go, Infrastructure, Security, Mobile), customer success, sales, marketing, and operations in the US, Canada, and UK, with some roles in Singapore.

## Why Work Here
- **Fully Remote & Flexible**: Tailscale is a fully remote company with team members across the US, Canada, and UK. Flexible working hours are core to the culture – employees are trusted to manage their time around their lives (family, appointments, etc.).
- **Competitive Total Rewards**: Competitive salaries, generous equity incentive plans, group health benefits with no waiting periods, flexible sick days, and an employee assistance program.
- **Work-Life Balance**: 26 weeks of paid parental leave, flexible paid vacation, 12 paid company holidays, and a full holiday closure from Dec 24 to Jan 1.
- **Workspace Support**: Company-provided laptop (Mac/PC), monthly internet reimbursement, and a “build your own workstation” bonus.
- **Engineering Culture**: Strong emphasis on open-source contribution, Go programming, and systems-level engineering. Many team members are active in the Go, NixOS, and SQLite communities.
- **Inclusive & Diverse**: The company is committed to diversity and inclusion, with a team not bound by geography, lifestyle, or life stage. They provide accommodations throughout the interview process.
- **Interview Process**: For technical roles: Recruiter Interview → Hiring Manager Interview → 2-3 Team Interviews → Technical Working Session → Offer. For non-technical roles: Recruiter → Hiring Manager → 2-3 Team Interviews → Offer.

## Sources
1. [tailscale.com](https://tailscale.com/) – Official website
2. [tailscale.com/company](https://tailscale.com/company) – About page, team, investors, guiding principles
3. [tailscale.com/careers](https://tailscale.com/careers) – Careers page, perks, benefits, culture
4. [job-boards.greenhouse.io/tailscale](https://job-boards.greenhouse.io/tailscale/jobs/4525230005) – Current job openings
5. [jobsbyculture.com](https://jobsbyculture.com/blog/working-at-tailscale-2026) – Employee culture review (2026, ~290 employees)

## Other roles at Tailscale

- [Infrastructure Engineer](https://feeny.ai/job/infrastructure-engineer-tailscale-united-states-8fvm5w9w0qtt) — United States
- [Infrastructure Engineer](https://feeny.ai/job/infrastructure-engineer-tailscale-canada-4ewrr4nkwx0n) — Canada
- [Senior Web Experimentation Manager](https://feeny.ai/job/senior-web-experimentation-manager-tailscale-united-states-6m7d0bt7z2fk) — United States
- [Senior Web Experimentation Manager](https://feeny.ai/job/senior-web-experimentation-manager-tailscale-canada-v219v0jc1kfy) — Canada
- [Senior Solutions Engineer, Enterprise](https://feeny.ai/job/senior-solutions-engineer-enterprise-tailscale-united-states-dathcnv5kzrm) — United States
- [Senior New Business Account Executive](https://feeny.ai/job/senior-new-business-account-executive-tailscale-toronto-zctksfgkrbrw) — Toronto, Canada
- [Customer Account Executive](https://feeny.ai/job/customer-account-executive-tailscale-vancouver-nm88rz72a6es) — Vancouver, Canada
- [Software Engineer, Networking (Features)](https://feeny.ai/job/software-engineer-networking-features-tailscale-united-states-d4rdee9vbtq2) — United States
- [Software Engineer, Networking (Features)](https://feeny.ai/job/software-engineer-networking-features-tailscale-canada-dqep6hhnwys6) — Canada
- [Senior Customer Account Executive](https://feeny.ai/job/senior-customer-account-executive-tailscale-san-francisco-y2r500pswgk0) — San Francisco, CA