Associate Director, Engineering

Job Description Summary At Castlight, we are looking for an Associate Director of Engineering to lead a core pillar of our technology team. Reporting directly to the VP of Engineering, you will be responsible for building and scaling multiple engineering teams and services to create GenAI and ML-powered consumer-grade experiences designed to simplify the complex world of healthcare navigation. We are seeking a mission-oriented "navigator of complexity" who can recruit top-tier talent, drive aggressive product roadmaps, and operate in the sticky-nuanced world of healthcare access.

How will you make an impact & Requirements

Who You Are An Impact-Driven Leader:
You're the engineering leader who loves a successful launch and obsesses over how the tech your team builds actually works. You hear a complex target date and immediately start mapping out a path to beat it.

Mission-Oriented:
You come to work every day wanting to know that what you build matters - to users, to customers, and to the systems that help people get the care they need.

A Navigator of Complexity:
You can navigate the ambiguity of new technology and the complexities of data workflows. You walk the tightrope between business and tech, helping connect talent-rich teams to generate outcomes that make a difference.

A Culture Builder:
You know how to unblock people, drive an aggressive roadmap, and foster a unified culture of excellence across teams.

Talent First:
We believe in talent and drive over a perfect checklist. The only non-negotiable is this: you have a proven track record of leading multiple software engineering teams that have delivered complex, high-scale technology-enabled services.

Who We Are At Castlight, we’re making it as simple as humanly possible for people to navigate the complicated, often frustrating, world of healthcare. We partner with America’s largest employers and health plans, transforming employee benefits into a deeply personalized and guided journey for millions of users. What we build genuinely helps people live happier and healthier lives.

What You'll Do Reporting directly to the VP of Engineering, you’ll be responsible for a core pillar of the Castlight technology team - building GenAI and ML powered consumer grade experiences to power care navigation powered by Google Cloud Platform. We urge engineering-driven ideas and will rely on you to bring them to reality. You will have the autonomy to make a massive impact and own your results,  This Role You'llLead and Grow:
Support and scale multiple engineering teams, recruiting top-tier talent to execute on an aggressive and meaningful product roadmap.

Execute the Vision:
Partner closely with product, design, and architecture leaders to turn complex ideas and care journeys into simple user realities.

Modernize and Scale:
Own the outcomes of your organization, ensuring the technology you oversee is fast, accurate, and high-performing.

Foster Excellence:
Cultivate a culture of high-quality execution and continuous delivery where accountability is everything.

Skills & Qualifications Engineering Leadership: 8+ years of software development experience with 4+ years leading multiple engineering teams or managing managers.

Technical Scale:
Deep experience architecting and maintaining high-availability, distributed systems and cloud-based services (We’re on GCP - but AWS/Azure experience fine).Operational Maturity:
Proven expertise in modern SDLC practices, including CI/CD, automated testing, and agile development.

Talent & Network: A strong track record of recruiting & retaining senior talent.

Data & Complexity:
Comfort managing complex data workflows and modernizing legacy codebases without interrupting service.

Communication:
The ability to translate complex…