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.

The Role:

We are hiring an AI Operations Associate to design, build, and scale the AI and automation layer that powers Flagler Health's back-office and clinical operations. This leader will help take the company from ad-hoc scripts and manual workflows to a durable, systematic AI ops engine that compounds in value as the company grows.

Reporting to the CEO & CTO, this leader will own the AI & Automation function while working across BizOps, RCM, and Product to drive measurable operational leverage. This is not a "sit back and manage" role. As AI Operations Associate, you will operate as a player-coach, shipping automations from the front while building the systems, standards, and team that scale them.

You will own the company's automation roadmap, refine and operationalize how we capture and translate workflows into production systems, and help evolve the operating model to support more complex EHR integrations, larger provider footprints, and continued expansion across multi-site organizations. This is a high-impact role at a critical inflection point, with the opportunity to shape how Flagler scales its operational backbone.

Key Responsibilities

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

• Workflow discovery: Shadow clinical and back-office teams to understand workflows and find the highest-ROI automation opportunities, then build repeatable processes for capturing, shipping, and monitoring automations in production.

• EHR integrations: Lead data integrations across major EHRs owning the error handling, and reliability of those pipelines.

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

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

• Vendor management: Scope and execute with automation vendors, holding them to delivery, quality, and reliability standards.

• Cross-functional alignment: Partner with Engineering on integration patterns, data contracts, and what belongs in product vs. ops.

• Operational discipline: Enforce documentation, monitoring, and change-management practices for reliable production systems and data-driven decisions.

• Customer voice: Act as a conduit between operators, clinicians, and internal teams, informing product and roadmap with workflow-level insight.

Requirements

• 1–3 years of experience in management consulting, software engineering, product management, or a similar analytical/technical role, ideally with exposure to high-growth or ambiguous environments.

• Strong problem-solving instincts with a 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: comfortable with APIs, light scripting (Python, JavaScript, or similar), and picking up new tools quickly. You don't need to be a senior engineer, but you should be able to read code, write automations, and debug your own work.

• Exposure to healthcare, operations, or regulated industries is a plus, but not required. We care more about how quickly you can learn the domain than what you've already seen.

• Strong written and verbal communication; able to translate between technical and non-technical stakeholders and write clearly for leadership.

• Comfort working cross-functionally with Engineering, Product, and Operations, and an ownership mindset about outcomes rather than scope.

• Bachelor's degree.

Non-Functional Skills & Cultural Fit

• Charismatic and credible leader who can inspire teams while holding a high performance bar.

• Thrives in fast-paced, high-growth environments and is comfortable operating through ambiguity.

• Highly execution-oriented with a willingness to roll up sleeves and stay close to the work.

• Resilient, adaptable, and competitive, with a strong drive to win.

• Balances strategic thinking with operational discipline.

Reasons to join Flagler Health:

• Fast-Growing Leader: Join a company with strong momentum and expanding adoption across provider organizations.

• Category Creation: Operate in a large, underserved market with limited direct competition.

• Compelling Product: Sell solutions with clear ROI, strong adoption, and increasing deal sizes.

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

• Industry Exposure: Build deep relationships across provider organizations and healthcare ecosystems.

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.