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About the RoleWe are seeking a talented and motivated full-time Product Manager, Aperture to help shape the product strategy for Tailscale's AI gateway. Aperture gives organizations visibility and control over how their teams use AI. It routes and secures LLM traffic through Tailscale's identity layer instead of distributing API keys, so security and platform teams can see who's using which models, enforce usage policy, and eliminate key sprawl.
You'll be the first dedicated PM on this team, working directly with our co-founder and working alongside a small, AI-native engineering team to take Aperture from its current early-stage footing into a core part of how Tailscale's customers adopt AI safely. This is a foundational role: you'll bring product rigor and customer focus to a team that's moved fast and proven real demand, and you'll have outsized influence over what Aperture becomes as it matures.
Key Responsibilities- Shape Aperture's product roadmap, in close partnership with our co-founder, Engineering Manager and the engineering team, translating a fast-moving, still-forming product area into clear priorities.
- Work directly with reference/design-partner customers to translate their AI governance and security needs into concrete product requirements.
- Partner with engineering to balance rapid prototyping with the production rigor required for an AI product customers depend on during their daily work.
- Represent Aperture externally - to customers, partners, and the community - as a credible voice on AI governance and enterprise AI adoption.
- Track and report on adoption, usage, and the metrics that matter for a product still establishing product-market fit.
- Partner with GTM and Customer Success as Aperture moves toward defined pricing and a repeatable sales motion.
What We Are Looking For- 3-5 years of product management experience (can include experience in other technical customer facing roles, e.g. SE or FDE), including meaningful time in an early-stage or 0-to-1 product context
- Comfort with ambiguity and fast, shifting priorities - this is a small team still defining its own scope.
- Experience building products for technical buyers (IT, security, or platform teams), since Aperture's customers are CISOs, platform engineers, and IT admins.
- Strong technical fluency - able to work credibly with engineers building in Go and go deep on identity, security, and AI-agent workflows.
- Excellent written and verbal communication, including the ability to represent the product externally.
Nice to Have- Prior product experience in AI/LLM infrastructure, developer tools, or identity/security products.
- Familiarity with the AI gateway landscape (e.g., LiteLLM, Portkey, Kong AI Gateway, Cloudflare AI Gateway) and how Aperture's identity-based approach differs.
- Experience partnering with GTM to bring a nascent product category to a defined pricing and sales motion.
- Public technical writing, conference talks, or community engagement.
- Hands-on experience with Tailscale, at work or at home.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.
CAN Pay Range
$209,040-$296,140 CAD
What We Offer- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. 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 job description.
- 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.
- Connect with other Tailscalars IRL. 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. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. 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. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
- 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).
