CareDev

About the Role

We're a healthcare technology company building a SaaS platform used by healthcare organizations across the U.S. Our engineering organization has grown, and we're ready for a hands-on leader to take the whole technical function — Frontend, Backend, DevOps, Mobile, and QA — to the next level.

This isn't a maintenance role. We're bringing in a Head of Engineering to solve four specific problems: get us to fully AI-driven development instead of trial-and-error, fix performance issues that have resisted repeated page rewrites, own technical conversations directly with customers, and lead a growing team well.

What You'll Do

Move us to AI-driven development. Lead the shift from ad hoc, trial-and-error use of AI coding tools to a systematic, largely AI-driven development workflow across the team — with repeatable practices, tooling, and guardrails, not one-off experimentation.

Build AI-driven QA automation. Apply the same discipline to testing: design and roll out AI-driven test automation to raise QA coverage and speed, in place of today's manual-heavy process.

Fix performance at the root. Diagnose and permanently resolve the page-performance issues that repeated rewrites haven't solved. Own DevOps and infrastructure decisions that address root causes rather than patching symptoms page by page.

Own technical customer conversations. Work directly with customers to gather and clarify requirements, and communicate trade-offs, scope, and timelines clearly to customers and internal stakeholders alike.

Lead and grow the team. Manage and develop a multidisciplinary engineering organization, including team leads, hiring, and performance management as the team scales.

What We're Looking For

• Proven, hands-on experience leading a team through an actual shift to AI-driven software development — not just personal use of AI tools. You can point to concrete before/after results (velocity, defect rates, cycle time).
• Experience building or scaling AI-driven QA/test automation.
• A strong DevOps and performance-engineering background, with a track record of diagnosing and permanently fixing recurring application performance issues rather than patching symptoms.
• Prior experience managing multi-discipline engineering teams (frontend, backend, mobile, QA) of 10+ people, including managing team leads/managers.
• Excellent written and verbal communication skills; comfortable working directly with customers on requirements and translating between technical and non-technical stakeholders.
• 8+ years in software engineering, with at least 3 in an engineering leadership role.

Nice to Have

• Experience with U.S. healthcare software — ideally involving CMS programs, EHR/EMR integrations, or HIPAA compliance.
• Experience scaling an engineering org in a startup or scale-up environment.
• Still hands-on enough to review architecture and code when it matters, not purely a people manager.

The Team

You'll lead a growing, multidisciplinary engineering team spanning frontend, backend, QA, mobile, and business analysis.

You'll report directly to company leadership.

Tech Stack

• Backend: PHP (Symfony), microservices
• Frontend: React, TypeScript
• Data & messaging: MySQL/PostgreSQL, Redis, message queues
• Infrastructure: AWS, Docker, container orchestration, CI/CD
• Observability: Sentry, centralized logging

Compensation & Location

• Location: Fully remote — open to candidates anywhere.
• Compensation: Competitive, based on experience.
• Type: Full-time.