Job Overview
Location
Remote (United States)
Job Type
Full-time
Category
Operations
Date Posted
May 14, 2026
Full Job Description
📋 Description
- • Build and own Tailscale’s procurement function as the first dedicated hire, creating scalable processes for software, SaaS, cloud, data, and professional services spend while ensuring strong commercial discipline and appropriate legal, security, and financial controls.
- • Manage end-to-end procurement requests from intake through negotiation, contracting, and renewal management, prioritizing competing asks and aligning stakeholders on requirements and timelines.
- • Partner closely with Legal, Security, Finance, IT, Privacy, and business owners to coordinate contract review, security/privacy diligence, risk assessment, and approvals.
- • Design and implement scalable tooling and systems for procurement intake, contract and renewal tracking, approval routing, and reporting, plus playbooks and templates that drive consistency.
- • Own vendor lifecycle management, including renewal planning, usage review, supplier performance, and opportunities for consolidation or cost optimization.
- • Lead vendor negotiations directly on pricing, order forms, SLAs, SOWs, renewals, and key commercial terms to secure the best possible outcomes for Tailscale.
- • Support Tailscale’s mission of building a secure, easy-to-use Internet by enabling teams to acquire the tools they need efficiently and safely.
🎯 Requirements
- • 6+ years of experience in procurement, strategic sourcing, vendor management, or technology purchasing, ideally in SaaS or other high-growth technology environments.
- • Proven success building procurement processes, policies, and tooling from scratch and operating them independently—you’ve created structure where none existed.
- • Strong experience negotiating SaaS, cloud, data, and professional services agreements, including pricing structures, order forms, SLAs, SOWs, and renewals.
- • Ability to partner credibly with Legal, Security, Finance, IT, and business stakeholders, including working knowledge of vendor due diligence, security questionnaires, and privacy/compliance considerations.
- • Strong analytical and financial skills, including the ability 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 makes procurement an enabler rather than a bottleneck, and the judgment to know when more process is needed and when less is better.
🏖️ Benefits
- • An inclusive, flexible environment where you can be your authentic self, with flexibility in how and when you work to integrate work and life.
- • A competitive total compensation package including base salary, equity incentive plan, 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.
- • Remote-first company culture—most teams work fully remotely, with access to virtual and in-person social events and corporate co-working programs (e.g., WeWork).
- • Support for personal and professional development with $1,500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
- • Paid time off and a healthy work-life integration via a flexible, paid time off program.
- • A build-your-own home office setup: choose your own company-owned laptop (Mac or PC), receive monthly home internet reimbursement, and $1,000 USD to customize your workstation.
- • Generous parental leave program from day one, with top-ups for up to 26 weeks.
- • Annual company retreat, team off-sites, and opportunities to collaborate in person with teammates across Canada, the United States, and the United Kingdom.
Skills & Technologies
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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