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 RegardOur 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 goalsOwn and optimize engineering delivery processes, driving predictability, improving sprint planning, and sharpening estimation accuracyDesign an organizational structure that fosters accountability, eliminates bottlenecks, and improves cross-team collaborationMentor and upskill engineering managers, helping them grow as leaders and effectively manage their own teamsCollaborate cross-functionally with Product, Design, Customer Success, and Operations to ensure tight feedback loops and accelerate rapid iterationDefine and execute the engineering roadmap, establishing best practices for AI-powered, data-rich, and clinically reliable systemsMinimum Qualifications:BS degree in Computer Science or equivalent practical experience5+ 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 environmentsExperience leveraging generative AI and agentic coding workflows to accelerate the software development lifecycleProven track record of mentoring, upskilling, and managing engineering managersDemonstrated accountability for overseeing system reliability, scalability, and security across large-scale engineering initiativesStrong technical foundation in cloud infrastructure (e.g., AWS), modern CI/CD practices, and observability frameworksDemonstrated track record of partnering with Product leadership to successfully execute complex roadmaps from conception to completionPreferred Qualifications:Experience navigating the complexities of health tech or enterprise SaaS environmentsExperience leading engineering teams building with modern stacks like Python, TypeScript, or GoHybrid Work | Location | Work AuthorizationFor 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 areaOur 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 monthWe will provide relocation assistance to anyone who does not already reside in the NYC metropolitan areaFor those who enjoy working from our Manhattan office, we offer catered lunches and other fun perksAdditionally, hybrid employees have the flexibility to work from locations outside of their home office from up to 6 weeks per yearPerks & Benefits99% employer paid health benefits (Medical, Dental, and Vision) + One Medical subscription18 PTO days/yr + 1 week holiday breakMonthly health & wellness budgetCompany-sponsored team retreat + social eventsA sabbatical programOur 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.Compensation Range: $275K - $350K