Remote opportunity at
TailscaleProduct Manager, Aperture
Tailscale is seeking a full-time Product Manager, Aperture to lead product strategy for its AI gateway. Operating as a remote-first organization founded in 2019, the company…
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About This Role
Tailscale is seeking a full-time Product Manager, Aperture to lead product strategy for its AI gateway. Operating as a remote-first organization founded in 2019, the company builds software designed to securely connect people and devices across various environments. In this foundational position, the incumbent will serve as the initial dedicated product manager for the Aperture team, collaborating closely with the co-founder and a small engineering group. The role focuses on…
Job Description
Tailscale is seeking a full-time Product Manager, Aperture to lead product strategy for its AI gateway. Operating as a remote-first organization founded in 2019, the company builds software designed to securely connect people and devices across various environments. In this foundational position, the incumbent will serve as the initial dedicated product manager for the Aperture team, collaborating closely with the co-founder and a small engineering group. The role focuses on helping organizations gain visibility and control over artificial intelligence usage by routing and securing large language model traffic through an identity layer rather than API keys.
This opportunity is well-suited for a professional with a background in early-stage product development who can navigate shifting priorities and ambiguous scopes. The position requires frequent collaboration with technical buyers such as CISOs, platform engineers, and IT administrators, while representing the product externally to customers, partners, and the broader community. The successful candidate will guide Aperture from its early-stage status into a core offering that empowers customers to adopt artificial intelligence safely and efficiently.
Responsibilities
- Formulate and drive the product roadmap for Aperture in collaboration with the co-founder, engineering manager, and engineering team
- Engage directly with design-partner customers to convert security and governance requirements into clear product specifications
- Collaborate with engineering to balance rapid prototyping with production-grade reliability
- Act as an external spokesperson for Aperture, communicating with customers, community members, and partners regarding enterprise AI adoption
- Monitor and report on key adoption, usage, and product-market fit metrics
- Work alongside Go-to-Market and Customer Success teams to establish pricing strategies and a repeatable sales motion
Requirements
- Three to five years of product management experience or equivalent technical customer-facing roles such as sales engineering or field development
- Direct background working within an early-stage or zero-to-one product environment
- Familiarity with building technology for technical audiences including IT, security, and platform teams
- Technical fluency capable of working alongside Go engineers and addressing identity, security, and AI-agent workflows
- Strong verbal and written communication skills for external representation
Qualifications
- Previous product experience involving AI and LLM infrastructure, developer tools, identity solutions, or security software
- Knowledge of the AI gateway market including tools like LiteLLM, Portkey, Kong AI Gateway, and Cloudflare AI Gateway
- Experience partnering with go-to-market teams to launch nascent product categories into structured pricing and sales frameworks
- History of public technical writing, conference speaking, or community involvement
- Prior hands-on familiarity with Tailscale
Core Skills
Benefits
- Base salary between CAD 209,040 and CAD 296,140 per year
- Equity incentive plan and variable commission for eligible roles
- Comprehensive group benefits for employees and families with no waiting period, covering health, dental, and vision
- Dollar-for-dollar employer matching on retirement contributions up to 0.75 percent of eligible compensation
- Annual professional development allowance of USD 1,500 along with coaching and mentorship support
- Flexible paid time off policy and paid parental leave providing 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Home office setup including a choice of Mac or PC laptop, a monthly internet stipend, and a USD 500 workstation customization allowance
- Opportunities for travel through annual company retreats, team off-sites, and corporate co-working access via WeWork or similar spaces
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this position remote?
Yes, Tailscale operates as a remote-first company where most teams work fully remotely.
What is the salary range for the Product Manager, Aperture role?
The target base salary range for this role in Canada is CAD 209,040 to 296,140 per year, with individual offers varying based on skills and experience.
What experience is required to apply?
Candidates must have three to five years of product management or technical customer-facing experience, including time spent in early-stage or zero-to-one product contexts, along with strong technical fluency and familiarity building for technical buyers.
Sample Interview Questions
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