Solutions Engineer - Commercial (New Business)
Remote in CanadaTailscale
4+ YOECandidates need 4 to 5+ years in a customer-facing solutions or sales engineering role in networking or security software, strong networking and zero-trust knowledge, and the ability to explain technology in business terms.
Terraform, Pulumi, Ansible, CloudFormation, AWS, GCP
Solutions Engineer - Commercial (Expansion Sales)
Remote in CanadaTailscale
4+ YOECandidates need 4 to 5+ years in a customer-facing solutions or sales engineering role in networking or security software. Strong networking, zero-trust, IAM and cloud architecture skills are required.
Terraform, Pulumi, Ansible, CloudFormation, AWS, GCP
Software Engineer, Strategic Projects
Remote in CanadaTailscale
Candidates need strong experience hardening production software, a must-have of Go, comfort with third-party APIs and basic networking, and daily use of coding agents and LLMs. They should work well independently in a remote, fast-moving startup environment.
Go, Claude Code, Cursor
Software Engineer, Networking (Dataplane)
Remote in CanadaTailscale
Candidates need significant experience with networking software and diagnosing network issues, plus strong Go or low-level language skills such as C, C++ or Rust. Knowledge of routing, VPNs, NAT traversal and concurrent programming is expected.
Software development, Customer experience, Go, C, C++, Rust
Senior New Business Account Executive
Toronto, ONTailscale
2+ YOETailscale needs candidates with 2+ years of door-to-door or in-person prospecting or closing experience. They should have a technical background or curiosity, strong communication skills, and experience selling to senior technical buyers.
Salesforce, Gong
Security Infrastructure Engineer
Remote in CanadaTailscale
Candidates need experience securing cloud platforms, especially multi-cloud networks, plus container and authentication security. They also need programming skill in at least one language (Go is used) and Infrastructure as Code tools such as Terraform or Ansible.
AWS, Kubernetes, Terraform, Ansible, Go
Senior New Business Account Executive
Vancouver, BCTailscale
1+ YOECandidates need 1+ years of prospecting or closing experience in door-to-door or in-person sales, a drive to build a sales playbook, and a technical background or curiosity about technology. Strong communication and presentation skills and experience self-sourcing deals from discovery to closed won are also required.
Salesforce, Gong
Head of Legal
Remote in CanadaTailscale
Candidates need significant in-house legal experience at a technology company, a law degree and active bar membership. They also need experience scaling a legal function in a high-growth company and strong skills in advising executives and working with outside counsel.
Sales, Decision making, Communication skills, Leadership, Cybersecurity
Forward Deployed Engineer
Remote in CanadaTailscale
6+ YOETailscale needs 6+ years in a technical role, including 2+ years customer-facing. Candidates need networking, VPN and security knowledge, cloud and DevOps experience, and strong communication skills.
Docker, Kubernetes, AWS, GCP, Azure
Customer Reliability Engineer
Remote in CanadaTailscale
4+ YOECandidates need 4+ years in technical support or escalation at a SaaS or infrastructure company, with strong networking knowledge, overlay networking expertise (WireGuard, STUN), and code-level debugging skills in Go. Strong troubleshooting across Linux, macOS and Windows, plus clear communication with technical and non-technical audiences, are also required.
Go, pprof, Kubernetes, WireGuard, Python
Customer Account Executive
Vancouver, BCTailscale
1+ YOETailscale needs candidates with up to one year of quota-carrying experience in an AE or AM role. They should have sold developer or technical products, presented to senior executives, and used Gong or similar tools to manage pipeline.
Gong
Customer Account Executive
Toronto, ONTailscale
1+ YOECandidates need up to one year of quota-carrying sales experience, ideally selling developer or technical products. They should be comfortable presenting to executives, managing many deals at once, and working with sales engineering and customer success teams.
Gong
Commercial Legal Counsel
Remote in CanadaTailscale
Candidates need a law degree and active bar membership, plus meaningful experience advising technology companies on commercial deals. Strong negotiation skills, sound risk judgment and experience helping a legal function scale in a fast-growing company are expected.
contract lifecycle management tools