VP of Engineering (AI)

Location: Hybrid in the New York City metropolitan area, with three days per week in the office. More frequent office attendance is required during onboarding and team onsite weeks up to once per month. Relocation assistance is available for candidates outside the NYC metropolitan area. Candidates must be authorized to work in the United States without visa sponsorship.

Salary: $275,000–$350,000 per year, plus equity.

Company

Regard develops an AI-powered proactive documentation platform that reviews patient data in electronic health records, recommends diagnoses, and surfaces clinical evidence for healthcare providers.

What you will do

• Lead and scale a high-performing software engineering organization.
• Partner with the CTO, Head of Product, and cross-functional leaders to align technical execution with product priorities.
• Own engineering delivery processes, improving predictability, sprint planning, and estimation accuracy.
• Design an organizational structure that strengthens accountability, removes bottlenecks, and improves collaboration.
• Mentor and develop engineering managers while building leadership capabilities.
• Define and execute engineering practices and roadmaps for AI-powered, data-rich, and clinically reliable systems.

Requirements

• Bachelor’s degree in Computer Science or equivalent practical experience.
• 5+ years of software engineering experience, including 2+ years in senior engineering leadership roles at Director or VP level.
• Experience scaling engineering organizations to 30+ people in high-growth startup environments.
• Experience with generative AI and agentic coding workflows.
• Track record of managing and mentoring engineering managers and delivering complex product roadmaps.
• Strong foundation in cloud infrastructure such as AWS, modern CI/CD, observability, reliability, scalability, and security.

Nice to have

• Experience in health tech or enterprise SaaS.
• Experience leading teams using Python, TypeScript, or Go.

Culture & Benefits

• 99% employer-paid medical, dental, and vision coverage, plus a One Medical subscription.
• 18 PTO days per year and a one-week holiday break.
• Monthly health and wellness budget.
• Company-sponsored team retreat, social events, and a sabbatical program.
• Catered lunches and additional perks at the Manhattan office.
• Hybrid employees may work from locations outside their home office for up to six weeks per year.

Hiring process

• Successful completion of a background check is required.