Head of Deployment

Head of Deployment

Location: New York City (On-site, with 25-30% Customer Travel)

Reporting To: Founder

Compensation: $250,000–$400,000 + benefits

About Confido Health

Confido Health is the voice and workflow automation OS for healthcare. We sit inside revenue cycle, scheduling, prior authorization, and patient communication for high-volume specialty practices and PE-backed multi-site provider networks.

The bet? healthcare AI automation isn't won by the team with the best model - it's won by the team that gets closest to the operational mess of dozens of clinics and turns that proximity into a compounding system nobody else can reproduce.

Confido is Series A ($25M raised), scaling rapidly across enterprise specialty-care customers. Our model is forward-deployed: engineers and operators (FDEs and Deployment Strategists) live inside customer workflows, ship into production in weeks rather than quarters, and turn each engagement into a repeatable playbook.

Why This Role Exists

Confido's deployment engine - the FDE and Deployment Strategist pods that own customer outcomes - is the most strategic part of the company. As we scale across more enterprise customers, we need leader who will own everything that happens after a contract is signed: deployment velocity, customer expansion, the operating cadence with PE sponsors and exec buyers, and the senior hiring that keeps the pods strong.

You will own the entire post-signature lifecycle. If a customer is live, expanding, or renewing, that's a reflection of your engine. If a deployment stalls, you're the one unblocking it.

What You'll Own

1. Run the post-sales engine

• Own customer outcomes for every account post-signature. FDE and DS pods deployed against each customer report up to you.
• Set and hold the goals each pod is measured against - deployment velocity, AI handle rate growth, customer-acknowledged ROI, expansion.
• Unblock pods when they're stuck - on integrations, customer process, or internal product gaps. You're the escalation point.

2. Be the senior face for enterprise and PE customers

• Sit in the rooms with customer execs and PE operating partners. Run QBRs, lead strategic check-ins, own the narrative that lands with sophisticated buyers.
• Translate every deployment update into the financial impact story the executive sponsor cares about.
• Structure non-standard commercial deals - pricing, expansion SOWs, multi-workflow engagements - and push back when terms don't make sense.

3. Hire, onboard, and grow the team that runs deployments

• Lead hiring for the FDE and DS pods. Run the loop, make the call, own the bar.
• Onboard every senior IC so they're shipping into customer environments fast.
• Build the playbook that lets new pods ramp quickly without re-learning what the last pod already figured out.

4. Quarterback the operating cadence

• Run the weekly leadership rhythm alongside the founders.
• Decide what gets escalated and what gets decided in your seat.
• Author the recurring artifacts - board updates, investor narratives, exec-buyer decks - at a quality bar that doesn't need editing by the founders.

What We're Looking For:

• You've run a post-sales or forward-deployed function before - at a startup where delivery, not sales, was the constraint. FDE, deployment/implementation leadership, technical customer success, or professional services at scale, ideally in a company selling complex technical product into enterprise or healthcare accounts.
• You're credible with sophisticated buyers. You've sat across the table from PE operating partners and hospital/practice-group executives and held your own - on outcomes, on commercial terms, on pushback.
• You can still go deep. You understand what it takes to ship into a customer's live environment in weeks, and you can tell the difference between a real blocker and an excuse.
• You've hired senior ICs into ambiguous, high-stakes roles and know how to spot the FDE/DS profile - technical enough to ship, operator enough to run a room, resilient enough to live inside someone else's mess.
• You operate like a founder. Comfortable owning a P&L-adjacent function, making calls without a playbook, and being judged on outcomes rather than activity.
• Healthcare, healthcare-adjacent, or other high-compliance enterprise domain experience is a strong plus - you understand why revenue cycle, scheduling, and prior auth are operationally brutal, and you don't need that explained to you.
• 8–12+ years total, with meaningful time in a leadership seat at a startup that scaled from early stage through Series B/C, ideally with direct forward-deployed, deployment, or delivery-leadership experience.

Benefits & Perks

• 401(k) with a dollar-for-dollar company match of up to 5%, immediately vested
• Group Coverage HRA (GCHRA) to help cover eligible out-of-pocket healthcare expenses
• Comprehensive medical, dental, vision, life, and disability insurance
• Wellness stipend to support your physical and mental wellbeing
• Annual Learning & Development allowance for courses, books, conferences, and professional growth
• Unlimited Paid Time Off (PTO) with an expectation that you take time to recharge
• Regular team lunches, celebrations, and company offsites
• Opportunity to grow your career alongside one of the fastest-growing healthcare AI companies

Pay: $250,000.00 - $400,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Flexible schedule
• Health insurance
• Paid time off
• Parental leave
• Professional development assistance
• Referral program
• Vision insurance

Work Location: In person