Vice President, Engineering

About the Company

Flagler Health is developing a clinical operating system tailored to modern musculoskeletal care. The company works with MSK provider groups and specialty clinics to help them expand, run more efficiently, and improve long-term patient care across acquisition, clinical workflows, and ongoing engagement. Its platform connects care delivery with clinic operations so providers can create more value throughout the full patient journey. Flagler Health has recently closed a Series B round and is now moving into its next stage of growth.

Role Overview

This senior executive position will play a key part in expanding the engineering organization, strengthening the technical foundation, and improving operational maturity. The VP of Engineering will lead a distributed team based in NYC and Vancouver while defining the architecture, processes, and systems needed to support a fast-growing healthcare product in a regulated environment. The role calls for someone who can build a strong engineering culture, deliver dependable and scalable technology, and create the technical base for long-term growth.

Key Responsibilities

• Direct, coach, and grow a distributed engineering team across New York City and Vancouver.
• Lead the engineering recruiting approach, hiring bar, organizational structure, and staffing plans.
• Set technical direction for backend services, infrastructure, third-party integrations, and overall platform architecture.
• Drive improvements in scalability and reliability for systems that support real-time patient communication through audio and SMS, along with asynchronous workflow processing.
• Own the infrastructure roadmap, including cloud design, CI/CD, monitoring, automated deployments, and operational excellence.
• Put in place engineering practices that support security, compliance, resilience, and high performance in a HIPAA-compliant setting.
• Work closely with Product and Operations leaders to align engineering priorities with company objectives and roadmap delivery.
• Raise engineering throughput, strengthen system reliability, and improve cross-team collaboration as the organization grows.

Required Qualifications

• Demonstrated success leading, managing, and scaling a distributed engineering organization, including responsibility for recruiting, hiring, and headcount planning.
• Strong capability in technical strategy, architectural standards, and major infrastructure decisions across backend systems and complex integrations.
• Extensive experience building and enforcing engineering standards and running compliant, fault-tolerant production environments, ideally within HIPAA or another regulated industry.
• Proven record of implementing reliability and scalability improvements for platforms handling real-time communications and long-running asynchronous data flows.
• Ability to partner effectively with Product and Operations leadership to turn business needs into a practical engineering roadmap.

Preferred Qualifications

• Background in healthcare technology or SaaS products at a mid-sized startup.
• Knowledge of 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 tools such as Git.
• Experience working in a monorepo environment such as Turborepo or Nx.
• Exposure to distributed data or batch processing tools such as Apache Spark or Databricks.
• Exposure to DevOps practices, including containerization, observability, and automated deployments.

Work Environment

This is a distributed remote team with hybrid offices in New York City and Vancouver. The role calls for regular, consistent in-person collaboration. The team culture is highly collaborative, with meetings and technical discussions conducted on video.

Application Process

Applications are routed into a single ATS and deduplicated internally, so candidates only need to apply once. The interview process includes an initial Flagler conversation to align on expectations, followed by 2 to 3 technical assessments depending on seniority; these may include interviews and a take-home exercise. No LeetCode-style testing is involved, and AI tools are allowed. Additional non-technical interviews with operations and executive leaders can be scheduled as needed to better understand the company, and the process ends with an offer and background check.

Company Values

• Persistence and ownership of outcomes: team members are expected to wear multiple hats and push through difficult problems.
• Personal and professional growth: learning, taking on challenges, and occasional failure are part of the culture.
• Low ego and quick feedback response: constructive criticism is welcomed and handled without taking things personally.
• Speed matters: the team values fast execution and thrives in a startup environment with a strong pace.
• Accuracy matters: the company aims to be detailed-oriented and correct as often as possible.