VP of Engineering

Regard • New York, NY

22h • $275,000 - $350,000 • Hybrid

About The Position

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.

Requirements

• 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

Nice To Haves

• Experience navigating the complexities of health tech or enterprise SaaS environments
• Experience leading engineering teams building with modern stacks like Python, TypeScript, or Go

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

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
• Relocation assistance

What This Job Offers

• Job Type: Full-time
• Career Level: Senior