--- title: 'Strategic Enterprise Account Executive at Tailscale' canonical: 'https://feeny.ai/job/strategic-enterprise-account-executive-tailscale-united-states-j72q76esbb7a' type: 'job' last_seen: '2026-10-20' --- # Strategic Enterprise Account Executive at Tailscale - **Company:** Tailscale - **Location:** United States - **Compensation:** $350k - **Work type:** remote - **Posted:** 2026-10-17 - **Last confirmed live:** 2026-10-20 - **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4744879005 ## 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 Tailscale makes it simple for organizations to securely connect people, devices, and workloads anywhere in the world. As adoption grows within the world’s largest enterprises, we’re launching a Strategic Sales team to support our next stage of growth. As a founding Strategic Account Executive, you’ll own a focused portfolio of organizations with 10,000+ employees, including Fortune 1000 and Global 2000 companies. You’ll lead complex opportunities from initial engagement through close and expansion, building executive relationships and connecting customer priorities with Tailscale’s capabilities. You’ll help define how we win in this market - developing outbound strategies, testing new approaches, and creating a playbook for future growth. Reporting to the Director of Strategic Sales, you’ll join a small, highly collaborative team and partner closely with executive leadership and teams across the business. ## Key Responsibilities - Own account strategy: Build account plans that connect customer priorities with opportunities across business units, geographies, and use cases - Create pipeline: Drive personalized outbound prospecting, partnering with SDRs and Marketing on coordinated account-based campaigns - Lead complex deals: Manage opportunities through negotiation and close, navigating long sales cycles, competitive pursuits, and complex buying processes - Build executive relationships: Earn trust with CIOs, CISOs, CTOs, and senior technical and business leaders while developing champions across the organization - Bring the right team together: Partner with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and grow strategic accounts - Shape the playbook: Test approaches, share what works, and bring customer feedback to teams shaping Tailscale’s product and enterprise strategy - Execute with discipline: Maintain clear qualification, accurate forecasts, and actionable account and opportunity plans ## What We Are Looking For - 5+ years of success as a top-performing enterprise or strategic seller in early stage, high-growth environments - Proven success selling to organizations with 10,000+ employees and closing complex six and seven-figure SaaS deals - Proven track record of consistently achieving or exceeding annual performance targets, with demonstrated YoY growth and sustained results - The ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and financial reviews - Strong business judgment, clear written and verbal communication, and a collaborative, accountable approach - Comfort with ambiguity and enthusiasm for building a sales motion while carrying a quota - Demonstrated commitment to CRM hygiene, including accurate opportunity management, pipeline tracking, and forecast reliability - Proven ability to lead value-based sales conversations and quantify business impact to build compelling ROI-driven business cases Preferred experience: - Serving as an early sales hire or helping build a new enterprise sales motion - Candidates must have strong technical acumen. Background in selling infrastructure, networking, cybersecurity, developer tools, or cloud software is a bonus You’ll Thrive Here If You… - Enjoy building from the ground up - creating account strategies, testing approaches, and shaping a playbook as you go - Love opening doors and winning complex enterprise deals through executive relationships, technical curiosity, and teamwork - Are energized by ambiguity and take initiative to create structure and momentum - Bring the same focus and discipline to building pipeline as you do to navigating complex negotiations and closing strategic deals - Want to help define how Tailscale wins and grows its largest enterprise customers 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. US Pay Range $350,000—$350,000 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 - [Program Manager, EPD Operations](https://feeny.ai/job/program-manager-epd-operations-tailscale-united-states-vhxf8tc001tg) — United States - [Program Manager, EPD Operations](https://feeny.ai/job/program-manager-epd-operations-tailscale-canada-mp6zqbgcdha4) — Canada - [Senior Customer Account Executive](https://feeny.ai/job/senior-customer-account-executive-tailscale-vancouver-jwgp948yyayw) — Vancouver, Canada - [Senior Customer Account Executive](https://feeny.ai/job/senior-customer-account-executive-tailscale-toronto-4ck2hgsdjdry) — Toronto, Canada - [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