RoleWe 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 Co-Founder & CEO, Albert Katz, and partnering closely with our Co-Founder & CTO Will Hu, 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.
Location: Based in New York City.
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 valuesThis is what you can expect of your teammates at Flagler:
- Persistence + ownership of outcomes: We wear many hats and aren't afraid to run through walls to solve hard problems.
- Personal + professional growth: We push ourselves to learn new things and embrace challenges, even if it means that we sometimes fail.
- Don't take things personally: We value and react quickly to constructive feedback.
- Speed is our ally: In the fast-paced world of startups, we understand the value of moving swiftly. We thrive on the adrenaline of working rapidly.
- Be Right: We are highly detailed oriented and try to be right, a lot.
