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Counterpart is building the first AI-native insurance company, redesigning operations from the ground up to empower small business owners with AI-driven management and professional liability underwriting and claims services.
As VP of Engineering, you will lead a flat-by-design engineering organization and own the technical vision, engineering operations, and people strategy for the function. You will represent Counterpart's technology strategy to the board and drive scaling through better infrastructure, context systems, and AI agents that compound engineer output.
Key responsibilities include:
- Evolving how the flat engineering organization scales with AI agents while maintaining high talent density and driving efficiency
- Shaping Counterpart's software-building approach in an AI-native world, partnering with the CEO, engineering leaders, and product managers
- Running Engineering as a function that allocates people and agents across competing initiatives, owning allocation decisions, engineering standards, delivery quality, and technical coherence
- Owning infrastructure that enables AI-native engineering: developer experience, AI and data platforms, and system infrastructure
- Hiring, performance management, compensation, and talent development for the engineering organization
- Ensuring systems meet high standards for reliability, observability, and security, including SOC 2, HIPAA, and NYC Cybersecurity compliance
- Representing Counterpart's technology capabilities internally and externally to leadership, partners, and investors
You bring 12+ years of engineering leadership experience, including leading organizations through multiple company-stage transitions and board-level engagement. You have a strong point of view on AI-native engineering—not just using AI tools, but deeply understanding how AI changes the engineer's role, organizational structure, and software economics. You possess deep technical fluency in system architecture, AI and data infrastructure, and deployment pipelines. You combine customer empathy with product sense, thinking about business and technology together. You have experience leading fully distributed teams with high trust and accountability. Experience in regulated industries (insurance, fintech, healthcare) is a strong plus, with understanding that compliance is built into systems, not bolted on afterward.
