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.
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
