Head of Strategy & Operations

This is a remote position.

Help Build the Next Chapter of a $750M Healthcare Technology Company

Our client, a scaling health tech company specializing in non emergency medical transportation services, has reached a pivotal stage in its growth.

With approximately $750M in annual run rate, meaningful profitability, and a national footprint serving some of the largest healthcare organizations in the country, their next phase of growth will be driven by operational excellence, scalability, and disciplined execution.

We're seeking a Head of Strategy & Operations to partner directly with the COO and lead one of the most impactful functions in the company.

This is not a traditional strategy role. It's an operating leadership opportunity for someone who enjoys solving complex business problems, leading high-performing teams, and turning analysis into action.

You'll work across Operations, Product, Finance, Client Success, and executive leadership to identify constraints, improve profitability, drive cross-functional initiatives, and help shape how the business scales.

The ideal candidate combines the structured problem-solving foundation of top-tier consulting with the practical operating experience gained inside a high-growth company.

You are equally comfortable leading a team, influencing executives, building a model, diving into messy data, and personally driving execution when the situation requires it.

For the right leader, this is an opportunity to help transform a fast-growing company into a true enterprise organization while working alongside an experienced COO and owning some of the most important challenges facing the business.

How you Operate:

This is not a 40-hour role. Ramp-up runs 55–70 hour weeks; steady state stays heavy. The work rewards what you put into it.

You'll work directly with a COO who is fast, blunt, data-obsessed, with a very high-bar - and also fair, deeply engaged, and one of the best operating leaders you'll work with. He values clear thinking, first-principles reasoning, and people who own outcomes rather than facilitate them. He loses trust quickly with vagueness, slow follow-through, or emotional reactions.

You'll have real influence, real ownership, and face real ambiguity. No one will hand you the playbook. The business is complex enough that ramping is in itself an achievement. The right candidate finds that energizing.

You'll likely succeed here if:

• You learn faster than the organization can teach you
• You ask questions that sharpen the problem, not just questions that help you read the room
• You're deeply structured, but not rigid
• You can make sense to a COO, a product leader, a call center operator, and an analyst — in the same day
• You prove problems with data and support solutions with data
• You're comfortable being hands-on in a senior role
• You operate in ambiguity without waiting for someone to define the problem
• You lead through service, clarity, and high standards — not control
• You have the stamina and ownership to ramp into a complex role quickly

This role is not the fit if you want a strategy-only seat, a purely managerial role, or a predictable 40-hour rhythm. The ramp will be intense. The problems will be ambiguous. The right person will find that energizing.

Requirements

Required Background:

• 8–10 years of total experience in strategy, operations, consulting, or a combination
• Strong consulting foundation — MBB (McKinsey, Bain, BCG) is strongly preferred
• Post-consulting experience leading a Strategy & Operations, BizOps, or Strategic Operations function at a high-growth, top-VC-backed startup
• Proven track record managing and developing people; comfort leading high-autonomy operators through influence and standards, not micromanagement
• Demonstrated ability to use data — Excel proficiency is non-negotiable, and you should be the kind of person who reaches for the spreadsheet before reaching for the meeting
• Communication range across executives, peers, and frontline operators — you can run a working session with the COO at 9am and a process review with the Call Center at 2pm without changing your effectiveness
• A history of operating in ambiguous environments where the problem isn't defined for you
• Willingness to operate as a true player-coach — still building the model, cleaning the data, or writing the memo when the work requires it

Preferred Background:

• MBA from a top program or equivalent achievement signal.
• Post-consulting experience leading Strategy & Operations, BizOps, Strategic Operations, or similar at a high-growth, VC-backed company.
• Experience scaling a team, operating function, or company through a meaningful growth phase.
• Experience working directly with C-suite or senior executive leadership.
• Familiarity with healthcare, logistics, transportation, marketplaces, or regulated operating environments.
• Advanced Data Skills (SQL, Python, R, etc.)

Benefits

Benefits

Our client offers a remote-first work environment, competitive compensation, and comprehensive benefits including:

• Career growth and development opportunities in a mission-driven organization
• Competitive salary, annual bonus opportunities, and equity options
• Remote with flexible hours
• Comprehensive medical, dental, and vision insurance
• 401(k) with company match
• Generous PTO, paid company holidays, and paid parental leave