FLAGLER HEALTH IS BUILDING THE CLINICAL OPERATING SYSTEM FOR MODERN MUSCULOSKELETAL CARE. We 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. Our platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle. We’ve recently raised our Series B and are entering our next phase of growth. THE ROLE: 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. WHAT YOU’LL DO: - 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 Required Qualifications: - 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. Preferred Qualifications: - 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) - Nice to have: Experience with distributed data or batch processing frameworks (e.g., Apache Spark, Databricks, or similar) - Nice to have: Exposure to DevOps practices, including containerization, observability, and deployment automation WORK ENVIRONMENT: - Distributed remote team with hybrid offices in NYC and Vancouver - This role requires regular and consistent in-person collaboration - We maintain a highly collaborative culture with video-on team meetings and technical discussions Application Process: - Apply to any one of the postings for this job. All applications from different job aggregators are sent to a single ATS and deduplicated internally. - Interviews: - Flagler intro: Q&A about who we/you are looking for in a new team member/team - Technical assessments: 2-3 (a mix of interview and take-home), depending on the candidate's level. No Leetcode. AI allowed. - Non-technical interviews with ops & c-suites: as many as you would like to get a sense of the company - Offer & background check 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. - 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.