VP of Engineering

Responsibilities

• Lead a flat-by-design engineering organization and evolve how it scales using AI agents
• Own the technical vision, engineering operations, and people strategy
• Partner with the CEO and product managers to refine software building processes in an AI-native world
• Manage resource allocation across competing initiatives and maintain technical coherence
• Oversee infrastructure including developer experience, AI and data platforms, and system infrastructure
• Manage hiring, performance, compensation, and talent development
• Ensure systems meet reliability, observability, and security standards (SOC 2, HIPAA, NYC Cybersecurity)

Requirements

• 12+ years of engineering leadership experience through multiple company-stage transitions
• Proven track record of engaging with boards, investors, and executive leadership
• Strong perspective on AI-native engineering and the economics of software delivery
• Deep technical fluency in system architecture and deployment pipelines
• Experience leading fully distributed teams with high accountability
• Experience in regulated industries such as insurance, fintech, or healthcare

Benefits

• Fully remote workplace with work-from-anywhere flexibility
• Unlimited vacation and no working birthdays
• Stock options and 401(k) retirement plan
• Health, dental, and vision coverage
• Home office allowance and wellness stipend
• Professional development reimbursement and book stipend

About the Company

Counterpart is building the first AI-native insurance company, pairing leading insurance experts with cutting-edge technology to empower small business owners to grow with confidence.