209K–296K CAD / year
Product Manager, Aperture
ProductRemote — Canada
Published on 2026-11-13
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About this role
Lead product strategy for Aperture, Tailscale’s AI gateway for helping organizations govern and secure AI use. As the first dedicated product manager for Aperture, you’ll work with the co-founder, customers, and engineers to develop the early-stage product into a core offering.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
The team
Aperture, Tailscale’s AI gateway product team.
Stack
GoLLMs
What you'll do
- Shape the product roadmap with the co-founder and engineering team.
- Turn design-partner customers’ AI governance and security needs into product requirements.
- Balance rapid prototyping with production reliability.
- Represent Aperture to customers, partners, and the community.
- Track adoption, usage, and product-market-fit metrics.
- Partner with GTM and Customer Success on pricing and a repeatable sales motion.
What we're looking for
- 3–5 years of product management or related technical customer-facing experience, including early-stage or 0-to-1 work.
- Comfort with ambiguity and changing priorities.
- Experience building products for technical buyers such as IT, security, or platform teams.
- Technical fluency, including the ability to work with Go engineers and discuss identity, security, and AI-agent workflows.
- Strong written and verbal communication skills.
Nice to have
- Experience in AI/LLM infrastructure, developer tools, or identity and security products.
- Familiarity with AI gateways such as LiteLLM, Portkey, Kong AI Gateway, or Cloudflare AI Gateway.
- Experience defining pricing and sales motions for a nascent product category.
- Public technical writing, conference talks, or community engagement.
- Hands-on experience with Tailscale.
Benefits
- Equity incentive plan.
- Health, vision, and dental coverage with no waiting period.
- Remote-first work and a corporate coworking program.
- Employer retirement contributions matched up to 0.75% of eligible compensation.
- Flexible paid time off.
- $1,500 USD annual professional development budget.
- Company laptop, monthly internet reimbursement, and $500 USD for home-office equipment.
- Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.