Director of Engineering (Hybrid, US-based, Miami Preferred) About Us Our client is a fast-growing, early-stage SaaS startup transforming the employee benefits and government contracting space. The platform is redefining how companies manage healthcare and fringe benefits through innovative applications of ICHRA and prevailing wage optimization. We're looking for a hands-on technical leader who brings both startup grit and engineering excellence-someone ready to operate as a technical co-founder in spirit. This role is perfect for a builder who can balance high-level strategy with in-the-trenches execution. What You'll Be Doing You'll serve as a "player-coach," owning the technology roadmap while managing development efforts day to day. This includes working with our current outsourced team, scaling our in-house capabilities, and setting the foundation for long-term technical growth. Your job is to accelerate product velocity without compromising quality, while integrating AI where it gives us an edge. Responsibilities Product & Technical Strategy Define and execute the technical vision and roadmap with leadership Translate business goals into clear technical priorities Optimize architecture for scalability, performance, and security Identify and implement opportunities to embed AI into the product Manage and transition from outsourced to in-house (or hybrid) development Lead and mentor a high-performing engineering team Establish engineering best practices, including DevOps and CI / CD Cultivate a collaborative, high-output culture that scales with the company What We're Looking For 5+ years of technical leadership experience in high-growth startups Proven success managing outsourced teams and hybrid engineering orgs Strong cloud (ideally AWS), DevOps, and security / compliance knowledge (HIPAA, SOC2) Experience integrating AI into SaaS products is a major plus Background in healthcare, SaaS, or GovCon is helpful Strategic mindset with a hands-on, get-it-done attitude What Success Looks Like You've transitioned us to a scalable hybrid or in-house development model Development velocity and quality have both improved significantly AI has become a core feature of our platform and process You've built a team and culture that others want to join Our platform is recognized as a category leader in the ICHRA space Competitive salary and equity Full benefits package A rare opportunity to shape the technical foundation of a breakout startup

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