Procurement Manager

Tailscale Inc.

Job Overview

Location

Remote (Canada)

Job Type

Full-time

Full Job Description

📋 Description

• As the first dedicated Procurement Manager at Tailscale, you will build and own the procurement function from the ground up, reporting to the VP of Finance, ensuring teams can securely and efficiently acquire the software and services they need while maintaining financial, legal, and security controls.
• You will manage the full procurement lifecycle—from intake and sourcing through negotiation, contracting, and renewal management—partnering closely with Legal, Security, Finance, IT, and business stakeholders to align on requirements, timelines, and risk assessments.
• Tailscale is a fully remote, fast-growing technology company backed by top-tier investors, building secure, easy-to-use networking software that connects people and devices globally, with a culture rooted in simplicity, ownership, and pragmatic problem-solving.
• In this role, you will design scalable procurement systems, tooling, and playbooks; drive cost optimization through vendor consolidation and renewal management; and develop expertise in strategic sourcing for SaaS, cloud, data, and professional services in a high-growth environment.

🎯 Requirements

• 6+ years of experience in procurement, strategic sourcing, vendor management, or technology purchasing, preferably in SaaS or high-growth technology environments.
• Proven ability to build procurement processes, policies, and tooling from scratch and operate them independently.
• Strong experience negotiating SaaS, cloud, data, and professional services agreements, including pricing, SLAs, SOWs, and renewals.
• Ability to partner effectively with Legal, Security, Finance, IT, and business stakeholders, including working knowledge of vendor due diligence, security questionnaires, and privacy/compliance requirements.
• Strong analytical and financial skills to evaluate total cost of ownership, benchmark pricing, manage renewals, and identify savings opportunities.
• Excellent communication and organizational skills with a service-minded approach that enables teams without creating unnecessary bureaucracy.

🏖️ Benefits

• Inclusive, flexible remote-first work environment where you can be your authentic self and integrate work and life on your terms.
• Competitive total compensation package including base salary, equity, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
• $1,500 USD annual professional development stipend, plus access to mentorship, coaching, and internal promotion opportunities.
• Generous parental leave program offering top-ups for up to 26 weeks from day one.
• Annual company retreat, team off-sites, and opportunities for in-person collaboration across Canada, the U.S., and the U.K.
• Home office support: choice of company-owned laptop (Mac or PC), monthly internet reimbursement, and $1,000 USD to customize your workspace.

Skills & Technologies

Remote

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Tailscale Inc.

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About Tailscale Inc.

Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.

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