Head of Strategy & Operations - Office of the COO

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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.

Headway is a ~$750M net revenue business growing ~70% year over year. We serve three customers (patients, providers and payers) across a fast-growing set of teams and initiatives. As we scale, the quality of our decisions, operating rhythms, and cross-functional execution are incredibly important and are becoming increasingly complex.

We are looking for a Head of Strategy & Operations, Office of the COO to partner closely with our COO, Rob Sadow. You'll serve as the COO’s right hand and point of leverage — running the company’s core operating processes, turning the company's most important priorities into action, strengthening how the executive team operates, and ensuring critical decisions and initiatives move forward with clarity and accountability.

This is a high-trust, high-impact, senior leader, individual contributor role reporting directly to the COO, with significant exposure to the executive team and the broader business.

You'll also work closely with the COO's Executive Assistant to ensure his time and attention are focused on the decisions and priorities that matter most.

What you’ll own in partnership with the COO

• Key company operating processes. Planning, OKRs, other important operating cadences. Keep each one lightweight and automate everything that doesn't need human judgment.

• Company execution. Own the weekly company OKR review and what comes out of it. When something looks off, go to the source: pull the data, join the conversation or call the meeting. Come back with a diagnosis, a recommendation and a named owner.

• The decision queue. Be the first stop for decisions that would otherwise go to the COO. Make the calls within agreed decision rights and send back what belongs with functional owners. Bring him the rest with options, a recommendation and a deadline, and make sure every decision leaves with an owner and a resolution date.

• Critical initiatives without a clear owner: Resolve new, high-stakes, cross-functional problems that would otherwise land on the COO's desk. Define the problem, align the stakeholders, and drive it to resolution or hand it to a permanent owner.

• Org health and productivity: In partnership with the HRBP and Finance teams, you’ll be one step ahead to ensure the org structure grows in alignment with the business. From supporting the scoping and hiring of key roles to making sure staffing ratios are aligned with talent competitors.

You’d be a great fit if...

• You’ve operated at an executive level and owned the outcome, as a COO or Head of Operations at an earlier-stage company, or as a VP, Senior Director of Strategy & Operations, or GM at a larger one. You can point to the results you were accountable for.

• You’ve run a company-wide process end to end, such as annual or quarterly planning, goal-setting, or business reviews. You can tell which parts of a process create clarity and which just add overhead, and you’ve cut the latter.

• You’ve worked directly with a CEO, COO, or executive team at a company that at least doubled in revenue while you were there. You’ve been trusted to attend meetings in an executive’s place and make decisions on their behalf.

• You’ve hired senior people through a rigorous process and built or rebuilt a team. You hold a high bar and can describe a candidate you passed on who was good but not great.

• You’re strategic with a demonstrated ability to break down a problem to its parts and push the team’s thinking to deliver a vision and execution plan.

• You’re an exceptional writer who can boil a complicated, high-stakes issue down to one page that makes the trade-off and the recommendation clear.

• You quickly figure out what matters in a messy situation. You go straight to the people and data closest to the problem, form a point of view, and bring options with a clear recommendation.

• You’ve owned board or investor materials, including the narrative and analysis behind them.

• You use AI and automation to take manual work out of a process rather than adding people to it.

Prior Chief of Staff experience, consulting experience, and an MBA are all welcome, but none are required.

Comprehensive benefits:

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.