Chief Technology Officer Jobs in Boca Raton, FL (NOW HIRING)

Job Description: Confidential Search | Value-Based Healthcare Organization Value-Based Care & Population Health | Hands-On Platform Engineering & AI Leadership Note: This is a confidential search. The hiring organization’s identity will be disclosed to qualified candidates during the interview process. Position At a Glance: · Title: Chief Technology Officer (CTO) · Employer: Confidential — Established Value-Based Healthcare Organization · Industry: Value-Based Care | Population Health | Healthcare Technology · Reports To: Chief Executive Officer · Employment Type: Full-Time, Exempt | Executive Leadership · Base Salary: Starting at $180,000+ annually, commensurate with experience · Additional Compensation: Performance-based bonus opportunities tied to platform delivery, AI impact, and company performance · Benefits: Comprehensive health, dental, vision, retirement, paid time off, and professional development About the Organization Our client is an established value-based healthcare organization operating across Medicare and commercial population health programs. The organization partners with physician practices, health systems, and care teams to deliver care that improves outcomes, reduces total cost of care, and captures meaningful performance under value-based arrangements. Behind that work is a sizable, growing technology and AI organization — more than thirty product, engineering, data, and machine learning professionals — that designs, builds, and operates the firm’s core technology platform. The platform is a multi-surface population health system used daily by clinical and operational teams across the organization’s value-based care programs. As the firm scales, leadership is doubling down on the platform itself and on AI, machine learning, and advanced analytics as the engine that powers its next chapter of growth. The Opportunity We are seeking a hands-on, technically credible Chief Technology Officer (CTO) to lead our client’s product, engineering, and AI organization through its next chapter of growth. This is a builder’s seat, not a strategy seat. You will lead a live, multi-surface platform — a web application used as the operational system of record, a cross-platform mobile experience for users in the field, and a browser extension that embeds patient context directly inside the clinical workflows clinicians already work in. You will own that platform’s roadmap, performance, and quality end to end, and you will direct how AI and machine learning are applied across it to drive measurable improvements in value-based care performance, financial outcomes, risk adjustment accuracy, care coordination, and operational efficiency. Why This Role Matters · You will own a production healthcare platform shipping across web, mobile, and EHR-embedded surfaces — used every day by the clinical and operational teams that power the organization’s value-based care programs. · You will lead and scale a meaningful, working technology and AI organization rather than starting from a whiteboard. · You will directly shape how AI is applied to value-based care, population health, and care management at scale. · Your work will support the organization’s value-based care programs, the participating physician practices and care teams behind them, and the patients they serve. · You will grow the Technology & AI group meaningfully over the next eighteen months, with a strong internship-to-hire pipeline. · You will report directly to the CEO and sit on the executive leadership team. · You will own a measurable, financially attributable platform and AI roadmap, with a quarterly ROI ledger and an annual Impact Report presented to the CEO and the organization’s governance leadership. What You’ll Do: Lead Product Engineering Across Every Surface · Own the architecture, delivery, reliability, and security of the firm’s core population health platform across all of its delivery surfaces — its web application, its cross-platform mobile experience, and the EHR-embedded browser extension that surfaces patient context inside clinical workflows. · Set and enforce engineering standards for a modern component-based web stack, a strongly typed JavaScript ecosystem, a cross-platform mobile architecture, and browser extension delivery against major ambulatory clinical systems. · Lead release management, environments, observability, error budgets, and incident response across the platform. · Drive the data foundation: the cloud data warehouse, transactional databases, ELT/ETL pipelines, FHIR-based clinical integrations, claims data feeds, HIE/ADT streams, and national lab feeds that the entire platform depends on. · Own the cloud footprint across major hyperscale cloud providers, the CI/CD pipeline, containerization, and infrastructure-as-code posture. · Establish a real product engineering discipline — discovery, design, delivery, and measurement — with clear pillar leads, OKRs, and quarterly platform releases. Make AI the Engine, Not a Side Project · Personally direct the AI and machine learning solutions embedded in the platform — risk stratification, risk adjustment accuracy, quality measure performance, care management workflows, utilization optimization, financial performance forecasting, document understanding, clinical letter generation, and decision support inside both the web and EHR-embedded surfaces. · Define and own the AI roadmap with prioritized, financially attributable use cases that benefit the organization’s value-based care programs across Medicare and commercial. · Evaluate build vs. buy vs. partner across foundation model providers, AI platforms, analytics tools, clinical data integration vendors, and clinical intelligence sources. · Ensure every production AI/ML model has a defined business owner, performance baseline, monitoring plan, and documented ROI. · Deliver an annual, Finance-attested Impact Report to the CEO and governance leadership documenting financial, quality, and operational outcomes from platform and AI investment. · Maintain a transparent ROI ledger and quarterly OKRs reviewed with executive leadership. Champion Responsible AI, Privacy & Security · Ensure all systems, data flows, and AI models comply with CMS value-based care program requirements, HIPAA, HITECH, the HIPAA Security Rule, and applicable state and federal regulations. · Establish and chair an AI Governance Committee covering model risk, bias, fairness, explain ability, and patient safety, aligned with the NIST AI Risk Management Framework. · Own enterprise cybersecurity strategy, including AI-specific threats such as prompt injection, model exfiltration, and data poisoning, alongside conventional application and cloud security. · Direct business continuity and disaster recovery planning for all critical systems. Lead and Scale the Engineering & AI Organization · Provide direct functional leadership to the technology and data leadership team, holding both accountable for technical execution, vacancy backfill, and AI and platform deliverables. · Set technical standards, architectural guardrails, and AI/ML engineering practices across the entire team. · Scale the organization meaningfully over the next eighteen months by adding senior capability in data engineering, cybersecurity and HIPAA compliance, cloud and infrastructure, AI governance and model risk, senior machine learning engineering, and product engineering across the web, mobile, and extension surfaces. · Build a structured internship-to-hire pipeline that converts high-performing interns into full-time technical talent. · Establish the engineering culture — quality bar, code review norms, on-call expectations, and craft standards — that lets the team continue to ship at the pace of a much larger one. Power the Organization’s Value-Based Care Portfolio · Architect and operate the data and analytics platform that powers benchmarking, financial modeling, risk stratification, and care coordination across the organization’s value-based care programs. · Deploy AI-driven decision support tools used by clinical leaders, operations managers, care coordinators, care managers, and physicians inside the platform’s web, mobile, and EHR-embedded surfaces. · Provide responsive build capacity to support new program onboarding, market expansion, and operational improvement projects. Own Vendor, Budget & Operations · Own the annual Technology & AI operating and capital budget with documented value realization and quarterly variance reporting. · Lead negotiation and ongoing management of all technology vendor contracts, ensuring HIPAA Business Associate Agreements, AI governance clauses, audit rights, and clearly defined SLAs. · Establish enterprise SLOs for availability, performance, and security across all mission-critical surfaces. · Provide technology oversight of the systems used to administer payment flows to participating providers and facilities accurately and on time. Communicate & Represent · Build and maintain real-time dashboards and reporting systems covering operational, financial, quality, and AI performance metrics. · Present platform, AI, and data performance updates to the executive team, governance and advisory bodies, clinical leadership, and participating practices. · Represent the organization at industry events, healthcare technology forums, governance meetings, and AI in healthcare conferences. What You Bring: Required Qualifications · Bachelor’s degree in Computer Science, Engineering, Data Science, Health Informatics, or a related technical field. Master’s or PhD strongly preferred. · Minimum 12 years of progressive technology leadership experience, with at least 5 years in a senior executive role (CTO, CIO, Chief AI Officer, VP of Engineering, or equivalent). · Proven, demonstrable platform delivery at scale. Documented track record of personally leading the design and delivery of a multi-surface software product — at minimum a modern web application, plus at least one additional first-party surface such as a cross-platform mobile experience, a desktop application, or a browser extension. You will be asked to walk our leadership team through the architecture, the team, the release model, the incidents, and the lessons learned. · Proven, demonstrable AI impact. Documented track record of personally leading AI/ML solutions into production at scale, with auditable financial, clinical, or operational outcomes. You will be asked to walk our leadership team through specific deployments, business cases, results, and lessons learned. Generic AI exposure will not qualify. · Direct experience leading technology in healthcare — value-based care, population health, risk-bearing organizations, payer/provider analytics, or healthcare technology platforms serving clinical operations. · Strong working knowledge of value-based care models, CMS quality and risk adjustment frameworks, HIPAA, HITECH, and the regulatory landscape governing population health and care management. · Hands-on, current technical fluency across modern web stacks, cross-platform mobile delivery, browser extension architecture, FHIR-based clinical integration, cloud data platforms, and modern AI/ML — including foundation models, retrieval-augmented generation, predictive analytics, MLOps, and model governance. · Demonstrated experience leading a product and engineering organization of meaningful scale through a partnered or matrixed reporting model, and influencing without sole direct authority where required. · Excellent leadership, negotiation, communication, analytical, and problem-solving skills, with the ability to translate platform and AI capability into business and clinical outcomes for non-technical stakeholders. Preferred Qualifications · Experience scaling an engineering organization through significant growth, new market or program onboarding, or company-level expansion. · Personal experience shipping a healthcare-grade browser extension or other in-EHR surface that meaningfully changed clinician workflow. · Published research, patents, or recognized industry thought leadership in healthcare AI/ML or healthcare platform engineering. · Prior experience reporting to a CEO and presenting to governance and advisory bodies. · Active relationships with leading AI labs, healthcare technology vendors, and the academic AI community. Compensation & Benefits · Base Salary: Starting at $180,000+ annually, commensurate with experience, demonstrated platform and AI impact, and prior executive scope. · Performance Bonus: Annual performance-based incentive tied to platform delivery, AI impact, quality outcomes, financial performance, and individual objectives. · Health & Wellness: Comprehensive medical, dental, and vision coverage. · Retirement: Employer-sponsored retirement plan with company contribution. · Time Off: Generous paid time off, paid holidays, and executive-appropriate flexibility. · Professional Development: Budget for executive education, conferences, certifications, and continued learning in AI, healthcare, and leadership. · Work Environment: Hybrid work model with collaboration across executive leadership and partner organizations. Why Join This Organization · Real Platform, Real Users: You will own a production system that hundreds of operators rely on every day, across web, mobile, and inside the EHRs clinicians live in. · Mission-Driven: Your work directly improves the quality and cost of care for the patient populations the organization serves. · AI as Engine, Not Side Project: Full executive backing and budget to make AI a foundational platform capability — owned by engineering, accountable to outcomes. · Executive Voice: Direct line to the CEO, governance and advisory bodies, and the executive leadership team. · Real Scope: Influence over the technology backbone of a growing value-based care and population health organization. · Growth Trajectory: Join an organization in active expansion, with clear plans to grow the Technology & AI group meaningfully over the next eighteen months. How to Apply Qualified candidates are invited to apply directly through this posting with a resume and a brief cover letter describing: 1. Two to three specific AI/ML initiatives you have personally led to production, including the business case, your role, measurable outcomes, and lessons learned, and 2. One multi-surface product launch you personally led — covering the surfaces involved (e.g., web, mobile, browser extension), the team and architecture, how you measured success, and what would have killed the launch if you hadn’t intervened. Selected candidates will be invited to a technical and executive panel interview where these examples will be discussed in detail. The hiring organization’s identity will be disclosed during the interview process. Application Materials: Resume, cover letter highlighting platform and AI impact, and (optional) supporting materials such as references, case studies, or pu