Vice President of Engineering

We are hiring a VP of Engineering to lead and scale the engineering organization behind a modern health benefits administration platform serving labor union benefit funds, TPAs, and healthcare organizations.

This is a hands-on executive leadership role responsible for engineering execution, organizational alignment, platform stability, architectural direction, delivery accountability, and operational maturity across multiple product and infrastructure teams.

You will oversee engineering leadership, partner closely with product and business stakeholders, and drive execution across a complex ecosystem that includes eligibility & enrollment, claims administration, payments, mobile applications, transparency solutions, APIs, integrations, and data platforms.

The ideal candidate understands how to operate in high-complexity environments where systems are interconnected, delivery matters, and engineering discipline is non-negotiable.

What You’ll Own

• Lead the overall engineering organization across multiple product and infrastructure teams

• Establish operational rigor, accountability, and delivery predictability across engineering

• Partner with Product, Architecture, Security, Infrastructure, QA, and Release Management leaders

• Drive engineering execution from roadmap through production delivery

• Improve SDLC maturity, release quality, observability, and engineering standards

• Ensure platform scalability, reliability, performance, and security

• Own technical execution and organizational prioritization during periods of rapid growth

• Help modernize and stabilize complex healthcare and benefits administration systems

• Work closely with leadership to translate business objectives into executable engineering plans

• Coach and mentor engineering managers and technical leads

• Drive architectural consistency and engineering quality across the platform

• Ensure teams are operating with strong Definition of Ready / Definition of Done discipline

• Create visibility into engineering risks, dependencies, delivery timelines, and operational health

Technology Environment

You do not need experience with every technology listed below, but strong architectural and systems thinking is required.

Core Stack

• Java / Spring Boot

• PostgreSQL

• REST APIs & event-driven systems

• AWS cloud infrastructure

• Docker / CI/CD pipelines

• Mobile and web platforms

• Data ingestion and analytics platforms

Product Domains

Experience in one or more of the following is highly valuable:

• Healthcare administration

• Claims processing

• Eligibility & enrollment systems

• Payments & reconciliation systems

• Financial workflows

• Enterprise SaaS platforms

• High-volume transactional systems

What We’re Looking ForRequired Experience

• 7+ years of engineering leadership experience

• Experience managing engineering managers and multi-team organizations

• Strong experience with Java Spring Boot and PostgreSQL

• Experience leading distributed engineering teams

• Strong systems architecture and platform thinking

• Experience scaling engineering processes and operational maturity

• Experience working directly with executive leadership and product stakeholders

• Proven ability to stabilize and improve complex systems under active development

Strongly Preferred

• Healthcare, insurance, benefits administration, fintech, or highly regulated industry experience

• Experience with claims systems, eligibility systems, payment workflows, or transactional financial platforms

• Experience building operational accountability and engineering process discipline

• Experience improving delivery predictability and reducing production instability

Leadership Traits We Value

• Ownership mentality

• Strong operational discipline

• Calm under pressure

• High standards without bureaucracy

• Direct communicator

• Systems thinker

• Pragmatic decision-maker

• Bias toward execution and measurable outcomes

• Comfortable operating in ambiguity while building structure

Team Structure

You will oversee:

• Multiple product engineering teams

• Infrastructure / Platform Engineering

• QA & release coordination functions

• Cross-functional technical initiatives

You will work closely with:

• Product leadership

• Data & architecture stakeholders

• Security and DevSecOps leadership

• Executive leadership

Location

• Miami, Florida preferred

• Hybrid leadership presence strongly preferred

Compensation

• Competitive salary

• Performance incentives

• Opportunity to help shape and scale a high-growth platform

About Us

We are building next-generation technology for labor union and healthcare benefit administration. Our platform spans eligibility, claims administration, payments, mobile engagement, transparency, communications, and operational workflows designed to modernize the benefits ecosystem.

We are looking for leaders who want to build meaningful systems that solve real operational problems at scale.

Pay: