VP of Engineering

Counterpart

Lead the engineering organization at Counterpart, an AI-driven insurance company. Oversee engineering operations, technical vision, and talent development in a fully remote setting.

Posted 5/14/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

Tech Stack

Tools & technologies

Cyber Security

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

12+ years of engineering leadership, with experience leading engineering organizations through multiple company-stage transitions. You have operated at a scale that regularly required engagement with the board, investors, and executive leadership. You 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. You have thought deeply about how AI changes the role of the engineer, the shape of the engineering org, and the economics of software delivery. You hold opinions on where the industry is going, and you can defend them. You also 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. You think about business and technology together, never one at the expense of the other. You constantly look for ways to enable the business through technology: building new capabilities while improving the systems underneath. You do not refactor for refactoring's sake, and you do not ship features on a foundation that cannot support them.
Experience leading fully distributed teams with high trust and high accountability.
Experience in regulated industries (insurance, fintech, healthcare, or similar) is a strong plus. You understand that compliance (SOC 2, HIPAA, state cybersecurity regulations) is a constraint you build into systems, not an afterthought you bolt on.

Benefits

Comp & perks

Fully remote workplace
Unlimited Vacation: We offer flexible time off, allowing you to take time when you need it.
Work from Anywhere: Counterpart is a fully distributed company, meaning there is no office. We allow employees to work from wherever they do their best work, and invite the team to meet in person a couple times per year.
Stock Options
Health, Dental, and Vision Coverage
401(k) Retirement Plan
Parental Leave
Home Office Allowance: to set up your home office with the necessary equipment and accessories.
Wellness Stipend
Book stipend
Professional Development Reimbursement
No working birthdays: Take your birthday off, giving you the opportunity to relax, enjoy your special day, and spend time with loved ones.
Charitable Contribution Matching

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI-native engineeringsystem architectureAI infrastructuredata infrastructuredeployment pipelinesengineering standardsproject delivery qualitytechnical coherencereliabilityobservability

Soft Skills

leadershipcustomer empathyproduct sensehigh accountabilityhigh trustcommunicationcollaborationstrategic visiontalent developmentperformance management

Certifications

SOC 2HIPAA