About the role

Role Overview

Counterpart is building the first AI-native insurance company and is redesigning its operations from the ground up. As VP of Engineering, you will lead a flat-by-design engineering organization, scale impact through improved infrastructure and context systems, and drive agents that compound each engineer’s output.

Responsibilities

Technical vision & strategy: Own the technical vision and represent Counterpart’s technology strategy to the board.
Engineering organization & operations: Evolve how a flat engineering org scales with agents; set standards for delivery quality and technical coherence.
AI-native engineering: Shape how Counterpart builds software in an AI-native world, leveraging AI to drive efficiency.
Infrastructure ownership: Own developer experience, AI/data platforms, and system infrastructure that enable AI-native engineering.
People leadership: Own hiring, performance management, compensation, and talent development; ensure high talent density.
Operating cadence & collaboration: Partner with the CEO, engineering leaders, and technical product managers to refine how the company builds and operates.
Resource allocation: Run engineering as a function that allocates people and agents across competing initiatives, owning allocation decisions and mechanisms.
Security, reliability, compliance: Ensure high standards for reliability, observability, and security; support compliance with SOC 2, HIPAA, and NYC Cybersecurity regulations.
External representation: Communicate technology capabilities and execution to leadership, partners, and investors.

Requirements

12+ years of engineering leadership, including leading engineering organizations through multiple company-stage transitions.
Experience at scale with frequent engagement with board, investors, and executive leadership.
Strong point of view on AI-native engineering beyond simply using AI tools.
Deep technical fluency across system architecture, AI/data infrastructure, and deployment pipelines.
Customer empathy and strong product sense; ability to connect business outcomes to technical decisions.
Experience leading fully distributed teams with high trust and accountability.

Nice to Have

Experience in regulated industries (insurance, fintech, healthcare, or similar).
Familiarity/experience with compliance expectations (e.g., SOC 2, HIPAA).

About Counterpart

Counterpart is building an AI-native insurance company focused on helping small businesses do more with less risk. It combines insurance expertise with technology to provide professional liability underwriting and claims services via the Counterpart platform.