Manager, Solutions Engineering – Enterprise

🕒 May 14

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• Manage and grow a small, senior team by coaching on live deals, developing judgment and technical depth, and hiring people who make the team better - not just bigger. • Set and uphold a high standard for enterprise discovery, technical evaluations, and successful rollouts that directly impact new customer acquisition and expansion. • Partner closely with Sales as a credible technical counterpart on complex enterprise opportunities, helping shape deal strategy, architecture, and execution quality. • Collaborate across Tailscale to improve how we run proofs of concept, explain technical value, and turn real customer feedback into product direction. • Provide clear, actionable feedback to Product and Engineering grounded in concrete customer use cases and enterprise constraints (not hypotheticals). • Stay current on cloud, DevOps, networking, and security trends, and help the team continue sharpening both technical instincts and communication skills.

🎯 Requirements

• Experience leading people, ideally as a working manager who still enjoys being in the details • Experience in a technical, enterprise customer-facing role such as Solutions Engineer, Sales Engineer, or similar • Clear, confident, opinionated communication skills—you can explain complex systems simply, read the room, and land a point without over-explaining • Solid understanding of networking and security fundamentals, including cloud environments such as AWS VPCs and Azure virtual networks • Hands-on technical background with experience in developer tooling, DevOps principles, and modern cloud architectures (CI/CD, infrastructure, APIs) • Ability to explain Tailscale’s value in your own words, grounded in customer outcomes and technical trade-offs rather than marketing language.

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self. • A competitive total compensation package. • Comprehensive group benefits with no waiting period. • Remote first company—most of our teams work fully remotely. • Connect with other Tailscalars IRL. • Support for your personal and professional development. • Paid time off and a healthy work-life integration. • A build-your-own home office setup. • Generous parental leave program from your first day.