Manager leading solutions engineering for enterprise at Tailscale. Collaborating across teams to provide technical expertise and grow a high-performing team.
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.
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.
Martech Solution/Enterprise Architect at Tiger Analytics enabling data - driven business value through hands - on architecture and integration. Focused on simplifying the Martech estate and improving tool interoperability.
Client Service Manager II enhancing pharmacy operations and supporting pharmacy clients at TELUS Health. Collaborating with internal teams and delivering innovative pharmacy solutions for better patient care.
Experienced regulatory architect developing architecture blueprints and application roadmaps at RBC. Collaborating with business leaders to drive delivery in regulatory initiatives.
Senior Customer Success Specialist responsible for leading client onboarding and implementation at a SaaS company. Creating exceptional client experiences and facilitating successful software adoption for various organizations.
Senior Consultant Data & Solution Architect at Keyrus in Montreal or Toronto, architecting data ecosystems and leading delivery teams with cloud - native technology.
Senior Solutions Architect specializing in Microsoft Purview and SharePoint for AI, Security, and Compliance. Leading enterprise - scale data governance, information protection, and compliance initiatives in a remote role.
AI Solutions Engineer at Affirm building AI - powered systems for the People function, transforming business problems into software solutions. Hands - on role requiring collaboration with non - technical stakeholders.
Solution Engineer at Salesforce collaborating with clients on innovative marketing strategies. Driving business performance and delivering technology solutions within strategic accounts in Montreal.
Senior Backend/API Developer for Ardhanarishvara project connecting individuals in education, employment, and healthcare. Responsible for backend architecture, API development, and integration services.