Manager, Solutions Engineering - Enterprise at Tailscale in Canada

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 We are looking for a Manager, Solutions Engineering – Enterprise & Mid-Market to join our rapidly growing team. The Solutions Engineering team partners with customers across the full lifecycle - from pre-sales through post-sales - by helping design, evaluate, and operationalize Tailscale in complex enterprise environments. This role exists to raise the quality of enterprise execution: better discovery, tighter technical evaluations, and clearer articulation of why Tailscale actually matters in a real-world architecture. The team works closely with Sales, Support, and Product, and collaborates deeply with Engineering and Marketing so customer feedback doesn’t disappear into a backlog. As Manager of Solutions Engineering, you will act as a true player-coach: showing up on important deals, coaching experienced SEs in real moments, and setting a high bar for how enterprise engagements should be run. If you care about people leadership, enjoy being close to the technology, and want to stay customer-facing while building a high-performing team of smart, self-sufficient solutions engineers, we should talk. Key Responsibilities 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. What We Are Looking For 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 This role is not a good fit if you are looking to move away from being technical, prefer managing through frameworks instead of real deal work, default to generic playbooks, or optimize primarily for future scale over present-day impact. We’re looking for judgment, energy, and credibility - not a perfectly adequate manager. 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. CAN Pay Range (OTE) $335,000—$368,500 CAD 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. 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.