Director of Procurement

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

How companies buy things sounds mundane. It isn't – not at Headway's stage. Every vendor decision shapes how fast we move, how much we spend, and whether our teams have the tools they need to help more people access mental healthcare. As we scale, procurement becomes a strategic lever: the difference between a company that operates with discipline and one that doesn't.

We're looking for a Director of Procurement who sees this not as a back-office function, but as one of the most operationally important roles at a company building something that matters. You'll work directly with our executive team and leaders across Finance, IT, Legal, Security, and Compliance – not just to manage vendors, but to build the systems and judgment that let Headway grow without losing control of cost or risk. You'll establish how we make purchasing decisions, evaluate partners, and create a procurement function that scales with the company.

If you're a detail-oriented leader who wants real influence on how a high-growth company operates – and you care about the mission behind the work — this role is built for you.

You Will

• Procurement strategy and policy.  Build and own the company's procurement function from scratch – intake, approvals, vendor selection, controls, and spend governance. Define when to centralize vs. delegate purchasing decisions so the org moves fast without sacrificing discipline. You'll drive strategic clarity on what the company is buying, why, and at what cost.
• Vendor lifecycle management.  Own the framework and standards that govern how Headway manages vendor relationships across the organization, from sourcing and selection through contracting, renewals, and performance management. Department leaders own their vendor relationships day-to-day; you'll ensure they have the structure, visibility, and support to do it well.
• Cost optimization and spend visibility.  Lead strategic sourcing initiatives across Headway's third-party spend across every major spend category – SaaS, AI, cloud, and professional services. You’ll step in directly on the highest-stakes negotiations and renewals. Build the reporting infrastructure that gives Finance and the executive team a real-time view of where money is going and where it shouldn't be.
• Procurement tooling and operational infrastructure.  Evaluate, implement, and optimize the systems that make the procurement engine run – intake tools, P2P platforms, contract management, and vendor management software. You don't just document the process; you build the infrastructure that runs it.
• Leadership advisory.  Serve as the go-to procurement partner for Finance, Legal, Compliance, IT, Security, and department leaders. Build the governance framework that balances speed and flexibility with cost discipline, risk management, and regulatory compliance.
• Team and function building.  Hire and develop a lean, high-impact procurement team over time. Set the talent bar, define roles and DRIs, and build the org structure that scales with Headway's growth.

You'd be a great fit if

• You've built a procurement function that didn't exist before, and you're proud of it. You've stood up intake processes, approval workflows, spend governance, and vendor controls from scratch, and you know what "excellent" looks like at every stage. You have deep category expertise across SaaS, AI, and professional services.You don't need to figure out the fundamentals; you bring a point of view on day one.
• You're obsessed with understanding exactly what Headway is buying, from whom, and whether we're getting the best possible outcome. You move fluidly between the line items of a contract and the category-level view of where third-party spend should go, and the business leaders around you trust both. You never let convenience win over value.
• You make the org better at buying, not just the procurement function. You earn trust across Finance, Legal, Compliance, IT, Security, and department leaders not by owning more, but by making their vendor decisions faster and smarter. You know how to influence category spend without direct authority, and you build partnerships that stick.
• You've personally won deals that mattered. You've negotiated complex, high-stakes agreements across SaaS, AI, cloud, and professional services, and walked away with terms that were genuinely favorable on cost, risk, and flexibility. You know the difference between a good negotiation and a great one, and you know which levers to pull to get there.
• You see AI as a competitive advantage for procurement, not a feature to explore someday. You actively use AI tools to drive faster vendor intelligence, sharper spend analytics, and greater efficiency across the source-to-pay cycle — and you bring that orientation to how you build the function around you.
• You bring structure to ambiguity — fast. With no existing procurement infrastructure to inherit, you're energized rather than unsettled. You stand up an intake process before anyone asks, define spend thresholds before the debate starts, and leave every sourcing process more rigorous than you found it.