Top Tech Jobs & Startup Jobs in Montreal

Own full-cycle recruiting from intake through offer across engineering, product, design, go-to-market, general and administrative functions. Develop sourcing strategies, assess candidates, negotiate offers, advise hiring managers, use recruiting data and market intelligence, and improve hiring processes. This contract role requires managing multiple complex searches in a fast-moving, distributed technology environment while delivering strong candidate experiences.

Partner with Account Executives to drive new commercial deals by leading technical discovery, solution architecture, demos, and POCs. Serve as trusted advisor across stakeholders, co-own pipeline and quota outcomes, produce enablement assets, and provide product and GTM feedback. Focus on networking, zero-trust, IAM, PAM, and cloud architecture.

Drive product positioning, messaging, and go-to-market for Tailscale by collaborating with product, sales, and marketing. Launch features, create sales enablement content, perform competitive analysis, represent PMM at events, and measure pipeline and revenue impact.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for vulnerabilities, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security analysis, and serving as an infrastructure-level subject matter expert during security incidents.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Extend visual identity, build reusable templates and design systems, present concepts, incorporate feedback, and manage multiple priorities. Collaborate with marketing, content, product marketing, web, developers, and other designers to deliver polished, consistent creative assets.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, and maintaining strong customer satisfaction. Troubleshoot across macOS, Windows, Linux, and mobile operating systems, explain technical concepts clearly, and collaborate with Customer Experience, Product, and Engineering teams to identify recurring user issues and improve the customer experience.

Serve as the technical lead for strategic customers: onboard, train, troubleshoot, and drive adoption of Tailscale. Build relationships, conduct QBRs, recommend best practices, escalate product feedback, and maintain customer-facing documentation to enable long-term success and expansion.

Build and maintain Tailscale's native Windows client using C#, XAML, and WinUI/Windows App SDK. Implement platform integrations and UI components, ensure compatibility across Windows versions, write unit and integration tests with Microsoft Testing Platform v2 and xUnit, and contribute to cross-platform client and backend code (including Go). Collaborate asynchronously within a distributed team and iterate quickly in a startup environment.

Lead and resolve high-severity post-sales technical escalations through deep-dive investigation, reproduction, and engineering handoff. Own customer calls, collect logs/evidence, file bug reports, monitor patterns, and improve tooling and runbooks in partnership with Support and Engineering.

Partner with Account Executives to drive new commercial business by leading technical discovery, solution architecture, demos, and POCs. Co-own pipeline, guide complex multi-stakeholder deals, provide product and GTM feedback, and build scalable enablement resources and demo environments for the SE team.