VP of Engineering

As VP of Engineering, you will lead and scale a high-performing software engineering organization, playing a pivotal role in shaping our technology and provider-facing platform. Reporting directly to the CTO, you will drive technical decision-making, guide cross-functional prioritization, and partner closely with product and senior leadership. You will champion engineering excellence, mentor and develop engineering managers, and lead the integration of cutting-edge generative AI technologies to unlock next-generation capabilities for our users. About Regard Our mission is to bring world-class healthcare to everyone. Regard is an AI-powered Proactive Documentation platform that advances how care is delivered by reviewing all patient data in the EHR to recommend diagnoses and surface clinical evidence. Regard drafts a note even before the physician sees the patient, enabling an approach that gets documentation right at the point of care - we call it Proactive Documentation. This improves quality of care, reduces physician burden, and improves hospital finances. We are excited by challenges, mission-oriented work, and meaningful relationships. We work closely with some of the top health systems in the country and are leading the change that healthcare - one of the largest and most inefficient industries in the world - needs. We want you to join us. Responsibilities: Partner closely with the CTO and Head of Product to align technical execution with company priorities and product roadmap goals Own and optimize engineering delivery processes, driving predictability, improving sprint planning, and sharpening estimation accuracy Design an organizational structure that fosters accountability, eliminates bottlenecks, and improves cross-team collaboration Mentor and upskill engineering managers, helping them grow as leaders and effectively manage their own teams Collaborate cross-functionally with Product, Design, Customer Success, and Operations to ensure tight feedback loops and accelerate rapid iteration Define and execute the engineering roadmap, establishing best practices for AI-powered, data-rich, and clinically reliable systems Minimum Qualifications: BS degree in Computer Science or equivalent practical experience 5+ years of software engineering experience, with 2+ years in senior engineering leadership roles (Director or VP level) Experience scaling engineering organizations to 30+ people within high-growth, dynamic startup environments Experience leveraging generative AI and agentic coding workflows to accelerate the software development lifecycle Proven track record of mentoring, upskilling, and managing engineering managers Demonstrated accountability for overseeing system reliability, scalability, and security across large-scale engineering initiatives Strong technical foundation in cloud infrastructure (e.g., AWS), modern CI/CD practices, and observability frameworks Demonstrated track record of partnering with Product leadership to successfully execute complex roadmaps from conception to completion Preferred Qualifications: Experience navigating the complexities of health tech or enterprise SaaS environments Experience leading engineering teams building with modern stacks like Python, TypeScript, or Go Hybrid Work | Location | Work Authorization For this role, Regard is currently only considering candidates who are authorized to work in the US without visa sponsorship, and are within either the New York City metropolitan area Our expectation for this role is to be in the office 3 days per week. We also require more frequent in-office work during the onboarding period and team onsite weeks up to once per month We will provide relocation assistance to anyone who does not already reside in the NYC metropolitan area For those who enjoy working from our Manhattan office, we offer catered lunches and other fun perks Additionally, hybrid employees have the flexibility to work from locations outside of their home office from up to 6 weeks per year Perks & Benefits 99% employer paid health benefits (Medical, Dental, and Vision) + One Medical subscription 18 PTO days/yr + 1 week holiday break Monthly health & wellness budget Company-sponsored team retreat + social events A sabbatical program Our goal at Regard is to provide and maintain a work environment that fosters mutual respect, professionalism and cooperation. Regard is proud to be an equal opportunity employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, national origin, ancestry, alienage or citizenship status, age, disability or handicap, sex, gender identity, marital status, familial status, veteran status, sexual orientation or any other characteristic protected by applicable federal, state or local laws. We celebrate diversity and are proud of our supportive, inclusive workplace. All candidates must successfully complete a background check as part of the hiring process.