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.

Senior Solutions

Engineer to drive technical success with resellers, MSPs, system integrators, and technology alliance partners. You will act as the primary technical counterpart for our channel motion—enabling partners to sell, deploy, and expand Tailscale successfully while co‑selling complex deals alongside Account Executives and Partner/Channel Sales Managers. This is a senior individual‑contributor role that blends deep networking/security expertise, consultative selling, partner enablement, and influence on product and go‑to‑market strategy.

You will co‑own pipeline outcomes, lead sophisticated technical engagements, and build scalable resources that multiply the impact of our partner community. This role is ideal for a senior SE who enjoys multiplying impact through partners while staying deeply technical and customer‑obsessed. You will help shape how Tailscale scales through the channel at a pivotal growth stage.

Collaborate with Channel Account Managers and AEs to identify, qualify, and close new and expansion opportunities through the channel. Lead technical discovery, solution architecture, demos, and proofs‑of‑concept (POCs) for partner‑sourced and co‑sell deals, often involving multi‑stakeholder enterprise or mid‑market environments. Serve as a trusted technical advisor to partners and their end customers on zero‑trust networking, secure connectivity, identity integrations, and emerging use cases (including AI gateway / Aperture‑related scenarios & PAM).

Develop and deliver partner technical enablement: training programs, certification content, demo environments, solution blueprints, reference architectures, and battle cards that help partners win and deploy Tailscale independently. Architect and guide complex multi‑party deals (partner + customer + Tailscale), aligning technical requirements with business outcomes and navigating competitive landscapes. Provide structured field feedback from partners and joint customers to Product, Engineering,



and GTM teams to influence roadmap priorities and packaging.

Build and maintain high‑trust relationships with key technical stakeholders at strategic partners; act as the escalation point for advanced architectural and integration questions. Collaborate cross‑functionally (Sales, Partner, Product, Customer Success, Support) to improve handoffs, technical win rates, and partner‑sourced revenue. Contribute to scalable SE processes, including reusable demo assets, partner‑facing documentation, and best‑practice playbooks. 6+ years in a customer‑facing Solutions Engineer, Sales Engineer, or Solutions Architect role within networking, security, infrastructure, or related software (prior experience supporting or selling through channel partners strongly preferred).

Direct experience enabling or co‑selling with MSPs, OEMs, VARs, system integrators, or technology alliance partners in the networking, security, or cloud infrastructure space. Proven track record of co‑owning pipeline and influencing quota outcomes in partnership with sales and/or channel teams. Deep understanding of zero‑trust networking principles, secure remote access/connectivity, and identity & access management integrations (SSO, SAML, OIDC, SCIM).

Strong networking fundamentals and troubleshooting skills: Hands‑on architecture and deployment experience with at least two major cloud providers (AWS, GCP, Azure) and hybrid environments.

Excellent communication and executive presence: ability to translate complex technical concepts into clear business value for both technical and non‑technical audiences (partners, end customers, and internal stakeholders).

Experience designing and delivering technical training or enablement content. Willingness to travel occasionally (approximately 15‑25%) for partner workshops, key customer meetings, conferences, and internal collaboration. Prior experience at a high‑growth networking, security, or infrastructure SaaS company (WireGuard, VPN, SASE, ZTNA, PAM, or adjacent domains is a plus).

Technical Skills:



Hands‑on experience with scripting or automation (Python, Bash, Go, Terraform/HCL, K8s or similar) for demos, POCs, or partner tooling. Familiarity with AI gateway, LLM access governance, or related emerging use cases. Previous exposure to Tailscale, WireGuard, or similar mesh‑networking technologies.

Experience building reusable solution architectures, partner playbooks, or technical certification programs. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. 335,000—$335,000 CAD We encourage you to help us break that statistic! An inclusive, flexible setting where you can be your authentic self.

This includes a base salary, an equity incentive plan and variable commission (for quota‑based roles). 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 . 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. 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. 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.

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). 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.

📌 Senior Solutions Engineer - Partners (Winnipeg)
🏢 WinsAbove
📍 Winnipeg