Flagler Health - AI Operations Associate
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 or equivalent practical experience. • 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. • Fast-Growing Leader: • Leadership Opportunity: Take ownership of and scale a growing sales organization at a critical inflection point. • Leadership Opportunity: • Category Creation: Operate in a large, underserved market with limited direct competition. • Category Creation: • Compelling Product: Sell solutions with clear ROI, strong adoption, and increasing deal sizes. • Compelling Product: • Meaningful Impact: Help providers improve efficiency, revenue, and patient outcomes. • Meaningful Impact: • High Earning Potential: Strong compensation tied to company growth and sales performance. • High Earning Potential: • Industry Exposure: Build deep relationships across provider organizations and healthcare ecosystems. • Industry Exposure:
Responsibilities
• Automation Ownership: Own the company's automation roadmap and consistently deliver measurable operational leverage against it. • Automation Ownership: • AI Ops Scaling: Stand up and scale the AI Operations function, with responsibility for hiring, onboarding, and developing additional operators and engineers as the company grows. • AI Ops Scaling: • Workflow Discovery: Stay close to the field by shadowing clinical and back-office teams to deeply understand workflows and identify the highest-ROI automation opportunities. • Workflow Discovery: • Automation Playbooks: Refine and operationalize repeatable, scalable processes for capturing workflows, shipping automations, and monitoring them in production. • Automation Playbooks: • EHR Integrations: Lead data integrations across major EHRs (eClinicalWorks, Athena, NextGen, and others) and own the contracts, error handling, and reliability of those pipelines. • EHR Integrations: • Tooling Strategy: Evolve the automation stack to match the workflow—APIs and portal integrations where possible, browser and desktop automation where necessary, and screen-level robots for last-mile flows. • Tooling Strategy: • AI Enablement: Stand up and maintain internal AI tooling (LLMs, agent frameworks, knowledge assistants) and train teammates to become power users of AI in their daily work. • AI Enablement: • Vendor Management: Lead scoping and execution with automation vendors, holding them to delivery, quality, and reliability standards. • Vendor Management: • Cross-Functional Alignment: Partner closely with Engineering to align on integration patterns, data contracts, and what belongs in product vs. ops. • Cross-Functional Alignment: • Team Leadership: Coach and develop the team on AI tools through structured training, hands-on support, and ongoing guidance. • Team Leadership: • Hiring & Scaling: Continue building a high-performing AI Ops team with strong culture, accountability, and execution discipline. • Hiring & Scaling: • Operational Discipline: Enforce rigorous documentation, monitoring, and change-management practices to support data-driven decision-making and reliable production systems. • Operational Discipline: • Customer Voice: Serve as a key conduit between operators, clinicians, and internal teams, informing product and roadmap strategy with workflow-level insight. • Customer Voice:
Benefits
• OTE (cash): $100,000-$150,000. • OTE (cash) • Equity • PTO: Flexible paid time off policy. • Benefits: Health, dental, vision insurance. • Our values • Our values • This 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. • Persistence + ownership of outcomes: • Personal + professional growth: We push ourselves to learn new things and embrace challenges, even if it means that we sometimes fail. • Personal + professional growth: • Don’t take things personally: We value and react quickly to constructive feedback. • Don’t take things personally • 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. • Speed is our ally • Be Right: We are highly detailed oriented and try to be right, a lot. • Be Right
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