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 locat