Tailscale

Product Manager - Security & Compliance

Canada

Not SpecifiedCompensation
Junior (1 to 2 years)Experience Level
Full TimeJob Type
UnknownVisa
Internet Software & ServicesIndustries

Product Manager, Security & Compliance

About Tailscale

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Position Overview

We’re looking for a thoughtful and technically curious Product Manager to join the team at Tailscale, initially focused on Security & Compliance. Reporting directly to the Group Product Manager overseeing our largest offering, you’ll join a supportive team of senior product leaders who are deeply committed to your growth and success.

You’ll begin by owning clearly defined workflows around device approvals and posture enforcement, key features that help Tailscale confidently serve regulated customers such as banks and healthcare providers. As you build confidence, your responsibilities will expand into broader security and compliance areas of the product.

At Tailscale, we believe even security should feel intuitive and elegant. You’ll apply your foundational compliance and security knowledge, along with strong product taste, to design intuitive onboarding experiences, streamlined approval notifications, and actionable audit trails.

While this role is open to current product managers, we are also interested in candidates who are not product managers but are currently in security-focused design, solutions engineering, or other customer-facing roles and ready to step into product management. You’ll have structured mentorship from a senior product leader, including regular 1:1s, and dedicated support from experienced teams in product management, sales, marketing, and customer success.

Key Responsibilities

  • Initially own specific workflows, such as MDM/EDR integrations and posture checks, with clear support from senior PMs and engineers.
  • Collaborate closely with engineering and design teams to create intuitive compliance workflows, frictionless device onboarding, and actionable audit experiences.
  • Write clear product requirements, manage your feature backlog, and actively work to enable multiple engineering teams.
  • Regularly engage directly with customers (approximately 25% of your time), supported by Sales and Customer Success teams, through structured interviews and shadowing existing customer interactions.
  • Collaborate with design, engineering and UXR to translate enterprise security and compliance requirements into simple, user-friendly experiences.

What We Are Looking For

  • Required: 1-3 years in a product management or customer facing role with foundational exposure to security standards, compliance frameworks (e.g., SOC 2, ISO 27001, GDPR), and relevant industry best practices.
  • Required: Solid foundational knowledge in at least one of the following areas: device approvals, posture checks, RBAC, ACL management, audit logging, along with an eagerness to quickly learn the others.
  • Required: At least 3 hours of overlap in daily working hours with our UK-based engineering team.
  • Comfortable learning and engaging hands-on with the product at the command line.
  • Excellent written communication skills, especially when crafting clear, actionable product requirements and documentation.
  • Strong interpersonal skills. You genuinely enjoy collaborating cross-functionally, particularly with sales, marketing, and customer-facing teams.
  • Empathy for users, instinctively prioritizing clear, intuitive, and enjoyable experiences, even within technical contexts.

Nice to Have

  • Familiarity with Zero Trust architectures, VPNs, identity providers, or related security products.
  • Exposure to infrastructure-as-code or DevSecOps tooling, ex: GitOps, Terraform.
  • Experience working with

Employment Type:

Location Type:

Salary:

Skills

Security
Compliance
Product Management
Device Approvals
Posture Enforcement
Security & Compliance Design
Audit Trails
Customer-Facing Roles
Security-Focused Design
Solutions Engineering

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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