[Hiring] Associate Director, Engineering @Vera Whole Health

Role Description

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.

• Support and scale multiple engineering teams, recruiting top-tier talent to execute on an aggressive and meaningful product roadmap.
• Partner closely with product, design, and architecture leaders to turn complex ideas and care journeys into simple user realities.
• Own the outcomes of your organization, ensuring the technology you oversee is fast, accurate, and high-performing.
• Cultivate a culture of high-quality execution and continuous delivery where accountability is everything.

Qualifications

• 8+ years of software development experience with 4+ years leading multiple engineering teams or managing managers.
• Deep experience architecting and maintaining high-availability, distributed systems and cloud-based services (GCP preferred, AWS/Azure experience fine).
• Proven expertise in modern SDLC practices, including CI/CD, automated testing, and agile development.
• A strong track record of recruiting & retaining senior talent.
• Comfort managing complex data workflows and modernizing legacy codebases without interrupting service.
• The ability to translate complex technical concepts into clear business strategy for non-technical stakeholders.
• Bachelor’s degree in Computer Science, Engineering, or equivalent practical experience.

Requirements

• Mission-oriented and driven to make an impact.
• A navigator of complexity, able to connect talent-rich teams to generate meaningful outcomes.
• A culture builder who can unblock people and drive an aggressive roadmap.
• Proven track record of leading multiple software engineering teams that have delivered complex, high-scale technology-enabled services.

Benefits

• A competitive salary and benefit package.
• Excellent health, dental, and vision coverage that supports your whole self.
• Opportunity to lead a core pillar of our business, scaling critical teams and building new products.
• Work that matters, removing barriers between a person and the care they need.

Compensation Range

$158,804.00 to $238,207.00. The anticipated base salary range represents the Company's good-faith estimate of the compensation it reasonably expects to pay for this position at the time of posting. Actual compensation will be determined based on factors including experience, skills, qualifications, geographic location, internal equity, and business needs.