Vice President, Engineering

Flagler Health • New York, NY

2d • Hybrid

About The Position

Flagler Health is building the clinical operating system for modern musculoskeletal care. They 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. Their platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle. Having recently raised their Series B, they are entering their next phase of growth. This is a foundational executive leadership role responsible for scaling the engineering organization, the technical infrastructure, and the company's operational maturity. As VP of Engineering, you will lead a distributed engineering team across NYC and Vancouver while shaping the systems, processes, and architecture required to support a rapidly growing healthcare platform operating in a regulated environment. Success in this role means building a high-performing engineering culture, delivering reliable, scalable systems, and laying the technical foundation for long-term business growth.

Requirements

• Proven experience leading, managing, and scaling a distributed engineering organization, including direct ownership of recruiting, hiring, and headcount planning.
• Expertise in setting technical direction, architectural standards, and driving large-scale infrastructure decisions across backend services and complex integrations.
• Deep experience establishing and enforcing engineering standards and operating compliant, fault-tolerant production environments, preferably in a HIPAA or other regulated industry.
• Track record of driving and implementing reliability and scalability solutions, particularly for platforms handling real-time (audio/SMS) and long-running asynchronous data workflows.
• Demonstrated ability to partner effectively with Product and Operations leadership to translate business priorities into a clear, actionable engineering roadmap.

Nice To Haves

• Experience in healthcare technology or SaaS platforms at a medium-sized startup
• Familiarity with HL7, FHIR, or EHR integrations
• Experience with cloud platforms such as AWS, Azure, or GCP
• Hands-on experience with CI/CD pipelines, infrastructure automation, and version control systems (e.g., Git)
• Experience working in a monorepo setup (e.g., Turborepo, Nx)
• Experience with distributed data or batch processing frameworks (e.g., Apache Spark, Databricks, or similar)
• Exposure to DevOps practices, including containerization, observability, and deployment automation

Responsibilities

• Lead, mentor, and scale a distributed engineering organization across NYC and Vancouver
• Own engineering recruiting strategy, hiring standards, organizational design, and headcount planning
• Define and drive technical strategy across backend services, infrastructure, integrations, and platform architecture
• Guide scalability and reliability initiatives for systems supporting real-time patient communications (audio and SMS) and asynchronous workflow processing
• Own infrastructure strategy, including cloud architecture, CI/CD, observability, deployment automation, and operational excellence
• Establish engineering best practices for security, compliance, resiliency, and performance in a HIPAA-compliant environment
• Partner closely with Product and Operations leadership to align engineering priorities with company goals and roadmap execution
• Improve engineering velocity, system reliability, and cross-functional collaboration as the organization scales

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed