VP of Engineering

Remote. Posted 33 months ago

The role

You will lead a flat-by-design engineering organization and own the technical vision, engineering operations, and people strategy. You will scale impact through infrastructure, context systems, and agents while representing technology strategy to the board.

What you will do

Evolve how the flat engineering organization scales with agents
Ensure and retain high talent density
Drive efficiency by leveraging AI
Set the forward-looking technical vision
Partner with the CEO and engineering leaders to refine how the company builds and operates
Allocate people and agents across competing initiatives
Own engineering standards, delivery quality, and technical coherence
Own infrastructure for developer experience, AI and data platforms, and system infrastructure
Own hiring, performance management, compensation, and talent development
Ensure systems meet standards for reliability, observability, and security

Required qualifications

12+ years of engineering leadership
Experience leading engineering organizations through multiple company-stage transitions
Experience operating at a scale requiring engagement with the board, investors, and executive leadership
Strong point of view on AI-native engineering
Deep technical fluency in system architecture, AI and data infrastructure, and deployment pipelines
Customer empathy and product sense
Experience leading fully distributed teams with high trust and high accountability

Nice to have

Experience in regulated industries (insurance, fintech, healthcare, or similar)

Benefits

Unlimited Vacation
Work from Anywhere
Stock Options
Health, Dental, and Vision Coverage
401(k) Retirement Plan
Parental Leave
Home Office Allowance
Wellness Stipend
Book stipend
Professional Development Reimbursement
No working birthdays
Charitable Contribution Matching

About the company

Counterpart is building the first AI-native insurance company. The company believes in small businesses and helps them do more with less risk by pairing insurance experts with cutting-edge technology.