Associate Director, Engineering

Castlight Health

. Report directly to the VP of Engineering .

Posted 10/7/2026full-timeRemote • United StatesSenior💰 $158,804 - $238,207 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in leading and scaling engineering teams, delivering high-scale technology-enabled services, and executing product roadmaps. Proficient in architecting high-availability systems and translating technical concepts for non-technical stakeholders.

Highest-signal resume keywords

Leadership of Software Engineering TeamsHigh-Availability Distributed SystemsGoogle Cloud PlatformModern SDLC PracticesRecruiting Senior Talent

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Software DevelopmentCloud-Based ServicesCI/CDAutomated TestingAgile DevelopmentData Workflow ManagementLegacy Code Modernization

Soft Skills

AccountabilityCollaborationCommunication

Tools & Technologies

Google Cloud PlatformAWSAzure

Industry Keywords

Healthcare NavigationGenAIMachine LearningEngineering CultureUser Experience

Tech Stack

Tools & technologies

AWSAzureCloudDistributed SystemsGoogle Cloud PlatformSDLC

About the role

Key responsibilities & impact

Report directly to the VP of Engineering
Build and scale multiple engineering teams and services
Create GenAI and ML-powered consumer-grade experiences for healthcare navigation
Lead and grow engineering teams and recruit top-tier talent
Execute an aggressive and meaningful product roadmap
Partner with product, design, and architecture leaders to turn complex ideas and care journeys into simple user experiences
Own organizational outcomes and ensure technology is fast, accurate, and high-performing
Foster a culture of high-quality execution, continuous delivery, and accountability
Bring engineering-driven ideas to reality and own results end-to-end

Requirements

What you’ll need

Proven track record of leading multiple software engineering teams that have delivered complex, high-scale technology-enabled services
8+ years of software development experience
4+ years leading multiple engineering teams or managing managers
Deep experience architecting and maintaining high-availability, distributed systems and cloud-based services
Experience with Google Cloud Platform; AWS/Azure experience also acceptable
Proven expertise in modern SDLC practices, including CI/CD, automated testing, and agile development
Strong track record of recruiting and retaining senior talent
Comfort managing complex data workflows and modernizing legacy codebases without interrupting service
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

Benefits

Comp & perks

Competitive salary and benefit package
Health coverage
Dental coverage
Vision coverage
Opportunity to lead a core pillar of the business and scale critical teams
Resume-building work
Mission-driven work improving healthcare access and experience