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
