Product Manager, Workload Connectivity
Remote in CanadaTailscale
7+ YOECandidates need 7+ years of product management, ideally on developer-facing infrastructure products. They need strong fluency in cloud-native infrastructure such as Kubernetes, containers, networking and workload identity, plus commercial judgment and experience leading cross-functional teams.
Kubernetes, Tailscale
Manager, Commercial Expansion
Toronto, ONTailscale
1+ MgmtCandidates need at least one year of people management experience in B2B SaaS sales, plus a proven record coaching quota-carrying sellers. Strong sales process knowledge, data-driven decision-making, and excellent communication skills are expected.
Manager, Commercial Expansion
Vancouver, BCTailscale
1+ YOE1+ MgmtCandidates need at least one year of B2B SaaS sales people management experience and a proven record coaching quota-carrying account executives. Strong knowledge of the full sales cycle, data-driven team leadership, excellent communication, and ability to work from Vancouver three days a week are required.
Sales, Lead a team, Coaching, Customer insight, Team leadership, Cold calling
Senior Analyst Relations Manager
Remote in CanadaTailscale
5+ YOECandidates need 5+ years in B2B technology product marketing, communications or analyst relations, including at least one year working directly with analysts. Familiarity with firms such as Gartner and Forrester and strong communication and organizational skills are also required.
Community Engagement and Advocacy Manager
Remote in CanadaTailscale
3+ YOETailscale needs 3 to 5 or more years of community management, advocacy or developer community experience. Candidates should have strong communication skills, moderation experience and a curiosity about technology.
Discord, Reddit, Common Room
Product Manager, Identity
Remote in CanadaTailscale
4+ YOECandidates need 4 to 7 years of product management experience owning an identity or security product. They should be fluent in identity protocols such as OIDC, SAML, SCIM, WebAuthn and OAuth, and experienced shipping developer or security tools.
SAML, Microsoft Azure, Google Workspace, Onboarding, Customer insight, Identity and access management
Product Manager, Networking Features
Remote in CanadaTailscale
7+ YOETailscale needs a product manager with 7+ years of experience, including direct ownership of an application-layer connectivity product such as reverse proxies, gateways, service mesh, DNS, or secure tunneling. They need a track record of designing complex networking products and making data-informed decisions.
Kubernetes, Tailscale
Release Manager
Remote in CanadaTailscale
5+ YOECandidates need 5+ years in engineering operations, release management, or a similar software role, plus direct experience building or improving release processes. They must understand branching, build pipelines, feature flags and rollouts well enough to discuss them credibly with engineers.
Feature flag systems, Build systems, Deployment pipelines
Engineering Manager
Remote in CanadaTailscale
Candidates need substantial experience managing engineering teams, building high-availability production services, and running on-call and incident response. Hands-on Go development experience and the technical depth to weigh design tradeoffs are required.
Go
Security Software Engineer
Remote in CanadaTailscale
Candidates need proficiency in at least one programming language (Go is used) and one application platform. Prior safety-related technical experience, deep knowledge of web and API vulnerabilities, cryptography and networking protocols, plus the ability to work independently and asynchronously are required.
Go
Billing Engineer
Remote in CanadaTailscale
Candidates need several years of backend engineering experience focused on billing, payments, or financial systems, plus deep knowledge of SaaS billing models. Strong Go skills, SQL and data modeling, and experience with distributed systems and APIs are required.
Stripe, Metronome, Go, SQL
Staff Product Operations Manager
Remote in CanadaTailscale
8+ YOECandidates need 8+ years in product operations, program management or business operations, including designing an org's operating model. They need a record of starting high-impact operations initiatives, experience building customer insight systems, and strong remote written and verbal communication.
Jira, Discord, Reddit, GitHub
Documentation Platform Engineer
Remote in CanadaTailscale
Candidates need experience building and deploying documentation sites with static site generators or modern frameworks. They must be fluent in TypeScript, JavaScript and React, comfortable with Python, Git and CI/CD, and able to explain how LLMs use documentation.
Hugo, Docusaurus, NextJS, Astro, React, TypeScript
ABM Campaign Manager
Remote in CanadaTailscale
5+ YOETailscale needs someone with 5+ years of B2B marketing experience, including ABM campaigns for acquisition and expansion. Candidates should have hands-on skills in LinkedIn advertising, personalized landing pages, direct mail or gifting platforms, and campaign measurement.
LinkedIn Campaign Manager, Userled, Mutiny, Reachdesk, Sendoso, Salesforce
Front End Engineer
Remote in CanadaTailscale
Candidates need deep experience building production React applications at scale, plus strong knowledge of web security fundamentals such as CORS, CSRF, cookies and authentication flows. Experience building internal frontend platforms and communicating technical tradeoffs across teams is also required.
React
Integrations Partnerships Lead
Remote in CanadaTailscale
7+ YOECandidates need 7+ years in B2B sales engineering, solutions architecture or technical partnerships. They need strong technical knowledge of APIs, authentication, cloud, networking and security, plus the ability to negotiate and build business cases.
Microsoft Access, VPN, Security regulations, Sales, Packaging, Cybersecurity
Product Designer (Growth)
Remote in CanadaTailscale
3+ YOECandidates need 3 to 5 or more years of product design experience, ideally in onboarding, growth or monetization. Hands-on experience with A/B testing and analytics tools such as Amplitude or Pendo, plus comfort interpreting experiment results, is required.
Amplitude, Pendo
Head of Communications
Remote in CanadaTailscale
10+ YOECandidates need 10+ years in PR, product or corporate communications, ideally at high-growth B2B technology companies, with a proven record of earned media and strong writing and editorial judgment. Experience managing communications staff and agencies, advising senior executives and explaining technical products clearly is required.
Public relations, Leadership, Research, Cybersecurity, Improve business processes, Fundraising
Program Manager, EPD Operations
Remote in CanadaTailscale
Candidates need program or technical program management experience, ideally in a remote startup and working closely with Engineering and Product. They also need strong data skills, Jira and Snowflake reporting experience, and comfort working independently with ambiguity.
Jira, Snowflake, Notion, GitHub
Senior Customer Account Executive
Toronto, ONTailscale
2+ YOECandidates need at least 2 years of closing experience in an AE or AM role, with experience selling developer or technical products. They should be comfortable presenting to executives and managing many opportunities at once.
Gong
Senior Customer Account Executive
Vancouver, BCTailscale
2+ YOECandidates need at least 2 years of closing experience as an AE or account manager, ideally selling developer or technical products. Tailscale expects strong executive presentation skills, comfort managing many deals at once, and experience with Gong or similar pipeline tools.
Gong
Infrastructure Engineer
Remote in CanadaTailscale
Tailscale needs candidates with experience in CI/CD, secrets management, infrastructure as code and observability, plus distributed systems and running cloud services, preferably AWS. Kubernetes in production and Go are strong pluses, along with networking knowledge and clear written communication.
AWS, Kubernetes, Go
Talent Acquisition Sourcer (Contract)
Remote in CanadaTailscale
3+ YOECandidates need 3+ years of talent sourcing or recruiting experience, ideally in high-growth technology companies. They need strong research skills beyond keyword searches, strong passive-candidate outreach, and solid organizational and analytical skills with sourcing and ATS platforms.
ATS, sourcing platforms, GitHub
Talent Acquisition Partner (Contract)
Remote in CanadaTailscale
6+ YOECandidates need 6+ years of full-cycle recruiting experience, ideally in high-growth SaaS, cloud, infrastructure, or other technology companies. Strong skills in sourcing, candidate assessment, stakeholder management and offer negotiation are required.
Talent mapping tools, AI recruiting tools