VP of Engineering

Counterpart•Remote, OR

2d•Remote

About The Position

Counterpart is building the first AI-native insurance company. We are redesigning how we operate from the ground up so that every person carries real context, real ownership, and real leverage, and the system carries the rest. As VP of Engineering, you will lead our flat-by-design engineering organization. Scaling our impact through better infrastructure, better context systems, and agents that compound every engineer's output. You will own the technical vision, engineering operations, and people strategy for the function, and you will represent Counterpart's technology strategy to the board.

Requirements

12+ years of engineering leadership, with experience leading engineering organizations through multiple company-stage transitions.
Operated at a scale that regularly required engagement with the board, investors, and executive leadership.
Know what great engineering organizations look like at each stage and what structures break when the company outgrows them.
A strong point of view on what AI-native engineering looks like. Not just using AI tools.
Thought deeply about how AI changes the role of the engineer, the shape of the engineering org, and the economics of software delivery.
Hold opinions on where the industry is going, and you can defend them.
Know where the hype outpaces reality.
Deep technical fluency to form strong opinions on system architecture, AI and data infrastructure, and deployment pipelines.
Customer empathy and product sense.
Think about business and technology together, never one at the expense of the other.
Constantly look for ways to enable the business through technology: building new capabilities while improving the systems underneath.
Experience leading fully distributed teams with high trust and high accountability.
Experience in regulated industries (insurance, fintech, healthcare, or similar) is a strong plus.
Understand that compliance (SOC 2, HIPAA, state cybersecurity regulations) is a constraint you build into systems, not an afterthought you bolt on.

Responsibilities

Evolve how our flat engineering organization scales with agents.
Ensure and retain high talent density.
Drive efficiency by leveraging AI.
Set the forward-looking technical vision that supports the business.
Shape how Counterpart builds software in an AI-native world.
Partner with the CEO, engineering leaders, and technical product managers to refine how we build, how we operate, and how we compound output.
Run Engineering as a function that allocates its people and agents across competing initiatives.
Own the allocation decisions, engineering standards, delivery quality, and the mechanisms to ensure project teams maintain technical coherence while operating independently.
Own the infrastructure that enables AI-native engineering: developer experience, AI and data platforms, and system infrastructure.
Own hiring, performance management, compensation, and talent development for the engineering organization.
Partner with the Head of People and the Chief of Staff to ensure Engineering's people model and operations fit the company's operating cadence.
Ensure our systems meet high standards for reliability, observability, and security, including compliance with SOC 2, HIPAA, and NYC Cybersecurity regulations.
Represent Counterpart's technology capabilities internally and externally, aligning with leadership, partners, and investors to communicate vision and execution.