AI Operations Associate

Flagler Health is building the clinical operating system for modern musculoskeletal care.

We partner with MSK provider groups and specialty clinics to help them grow, operate more efficiently, and deliver better longitudinal care across patient acquisition, clinical workflows, and ongoing patient engagement. Our platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle.

We’ve recently raised our Series B and are entering our next phase of growth.

We are hiring an AI Operations Associate to build the AI and automation layer behind Flagler Health's back-office and clinical operations, taking us from ad-hoc scripts and manual workflows to a durable AI ops engine that compounds in value as the company grows.

Reporting to the CEO & CTO, you will own the AI & Automation function while working across BizOps, RCM, and Product to drive measurable operational leverage. You will operate as a player-coach, shipping automations from the front while building the systems, standards, and team that scale them. Success means an operating model that holds up as EHR integrations get more complex and our provider footprint grows.

What You'll Do:

• Own the automation roadmap and deliver measurable operational leverage against it

• Shadow clinical and back-office teams to find the highest-ROI automation opportunities, then build repeatable processes for shipping and monitoring them in production

• Lead data integrations across major EHRs, owning error handling and pipeline reliability

• Match the stack to the workflow: APIs and portal integrations where possible, browser/desktop automation and screen-level robots for last-mile flows

• Stand up internal AI tooling (LLMs, agent frameworks, knowledge assistants) and train teammates to become power users

• Scope and execute with automation vendors, holding them to delivery, quality, and reliability standards

• Partner with Engineering on integration patterns, data contracts, and what belongs in product vs. ops

• Enforce documentation, monitoring, and change management for reliable production systems

• Act as a conduit between operators, clinicians, and internal teams, informing product with workflow-level insight

Required Qualifications:

• 1–3 years of experience in management consulting, software engineering, product management, or a similar analytical/technical role, plus a bachelor's degree.

• Bias toward action: comfortable scoping an ambiguous problem, breaking it down, and shipping a working solution end-to-end.

• Genuine fluency with modern AI tooling (LLMs, agent frameworks, prompt engineering) and a clear sense of where AI works well versus where it breaks down.

• Hands-on technical aptitude with APIs and light scripting (Python, JavaScript, or similar). You don't need to be a senior engineer, but you should be able to read code, write automations, and debug your own work.

• Strong written and verbal communication, able to translate between technical and non-technical stakeholders, and comfort working cross-functionally with an ownership mindset about outcomes rather than scope.

Preferred Qualifications:

• Exposure to healthcare, operations, or other regulated industries. We care more about how fast you learn the domain than what you've already seen

• Experience in high-growth or ambiguous environments

• Familiarity with EHR integrations and clinical or back-office data pipelines

• Nice to have: experience with workflow automation or RPA platforms

How You Work:

• Charismatic and credible, able to inspire teammates while holding a high performance bar

• Thrives in fast-paced environments and comfortable operating through ambiguity

• Resilient and competitive, willing to roll up your sleeves and stay close to the work

• Balances strategic thinking with operational discipline

Work Environment:

• Based in our NYC office, with regular and consistent in-person collaboration

• Highly collaborative culture with video-on team meetings and technical discussions

Reasons to join Flagler Health:

• Fast-Growing Leader: Strong momentum and expanding adoption across provider organizations.

• Category Creation: A large, underserved market with limited direct competition.

• Compelling Product: Clear ROI, strong adoption, and increasing deal sizes.

• Meaningful Impact: Help providers improve efficiency, revenue, and patient outcomes.

• Industry Exposure: Deep relationships across provider organizations and the healthcare ecosystem.

 

Our Values:

This is what you can expect of your teammates at Flagler:

• Owner: We own our work like founders. We don't wait to be asked, and we pick up the problem nobody else has.

• Builder: We like making things from scratch. We don't need a playbook to start, and we'd rather ship a rough first version than wait on a perfect spec.

• Fast: We make quick decisions. We favor progress and respect process.

• Transparent: We communicate directly. We value merit and honesty, and we challenge assumptions, including our own.

• Curious: We explore new approaches and ask "why" often.