AI Operations Associate

About Flagler Health

Flagler Health is creating a clinical operating system for modern musculoskeletal care. The company works with MSK provider groups and specialty clinics to help them expand, run more efficiently, and improve long-term care delivery across patient acquisition, clinical operations, and ongoing engagement. Its platform supports providers across the full patient journey, helping them capture greater value throughout the lifecycle of care. The company has recently closed a Series B round and is now in its next growth phase.

Role Overview

Flagler Health is looking for an AI Operations Associate to design, implement, and scale the AI and automation layer that supports back-office and clinical operations. This person will help move the business from one-off scripts and manual workarounds to a reliable, repeatable AI operations engine that grows in value as the company expands.

Reporting to the Co-Founder & CEO, Albert Katz, and working closely with Co-Founder & CTO Will Hu, this role will own the AI and automation function while partnering with BizOps, RCM, and Product to create meaningful operational leverage. It is a hands-on builder role rather than a pure management position. The associate will work as a player-coach, delivering automations directly while also creating the systems, standards, and team needed to scale them.

The role includes owning the automation roadmap, improving how workflows are captured and turned into production systems, and helping evolve the operating model to support more complex EHR integrations, larger provider networks, and growth across multi-site organizations. Based in New York City, this is a high-impact position at a key stage of company growth.

Key Responsibilities

• Take full ownership of the automation roadmap and deliver clear operational gains against it.
• Build and scale the AI Operations function, including hiring, onboarding, and developing additional operators and engineers as the team grows.
• Spend time with clinical and back-office teams to understand day-to-day workflows and identify the automation opportunities with the strongest return.
• Create repeatable playbooks for workflow capture, automation delivery, and production monitoring.
• Manage data integrations with major EHR systems such as eClinicalWorks, Athena, NextGen, and others, including contract logic, error handling, and pipeline reliability.
• Choose the right automation approach for each workflow, using APIs and portal integrations when available, browser or desktop automation when needed, and screen-level robots for final-mile processes.
• Set up and maintain internal AI tools, including LLMs, agent frameworks, and knowledge assistants, and help teammates become effective daily users of these tools.
• Own scoping and execution with automation vendors while holding them accountable for quality, delivery, and reliability.
• Work closely with Engineering to align on integration patterns, data contracts, and decisions about what should live in product versus operations.
• Coach team members on AI tooling through structured training, practical support, and ongoing guidance.
• Continue building a high-performing AI Ops team with strong culture, accountability, and execution habits.
• Maintain disciplined documentation, monitoring, and change-management practices to support dependable production systems and data-driven decisions.
• Act as a bridge between operators, clinicians, and internal teams, bringing workflow-level insight into product and roadmap conversations.

Requirements

• 1 to 3 years of experience in management consulting, software engineering, product management, or another analytical/technical role, preferably in high-growth or uncertain environments.
• Strong problem-solving ability with a bias for action and the confidence to take an ambiguous issue from definition through to a working solution.
• Practical experience with modern AI tools, including LLMs, agent frameworks, and prompt engineering, along with good judgment about where AI is effective and where it is not.
• Hands-on technical comfort with APIs, light scripting in Python, JavaScript, or similar languages, and the ability to learn new tools quickly.
• Ability to read code, build automations, and troubleshoot your own work without needing to be a senior engineer.
• Experience in healthcare, operations, or regulated industries is helpful, though not mandatory.
• Clear written and verbal communication skills with the ability to translate between technical and non-technical audiences and communicate effectively with leadership.
• Comfort working across Engineering, Product, and Operations with a strong ownership mindset focused on outcomes.
• Bachelor's degree or equivalent practical experience.
• Charismatic and credible leadership presence with the ability to inspire others while maintaining high standards.
• Ability to thrive in fast-moving, high-growth settings and stay effective amid ambiguity.
• Strong execution orientation and willingness to stay close to the work and do what is needed.
• Resilience, adaptability, and competitiveness with a strong drive to win.
• Balanced approach that combines strategic thinking with operational discipline.

Compensation & Benefits

• Cash OTE: $100,000 to $150,000.
• Equity: competitive equity package.
• Time off: flexible paid time off policy.
• Insurance: health, dental, and vision coverage.

Company Values

• Persistence and ownership: team members take responsibility for outcomes and are willing to tackle difficult problems head-on.
• Growth mindset: the team values learning, stretching into new challenges, and accepting occasional failure as part of progress.
• Directness without ego: constructive feedback is welcomed and acted on quickly.
• Speed matters: the team values fast action and thrives in a rapid startup environment.
• Accuracy: attention to detail and a commitment to being correct are highly valued.

Additional Information

Location: New York City.

This is a full-time onsite role.

Employment is tied to a high-growth company operating in a large, underserved market with limited direct competition. The position offers the chance to make a meaningful impact on provider efficiency, revenue, and patient outcomes, while building deep relationships across healthcare organizations and the wider ecosystem.

The role is positioned at a critical inflection point and includes the opportunity to help shape how the company scales its operational backbone.