VP of Engineering at Counterpart

Counterpart is committed to empowering small businesses to achieve more with less risk. By combining expert insurance knowledge with cutting-edge technology, Counterpart enables small business owners to grow confidently. The platform brings together exceptional underwriters, trusted insurance brokers, and prominent insurance carriers to support small businesses through AI-driven management and professional liability underwriting and claims services.

Counterpart is actively building the first AI-native insurance company, redesigning operations from the ground up. This approach ensures every individual holds real context, ownership, and leverage, while the system handles the rest.

VP of Engineering Role at Counterpart

As the VP of Engineering, you will lead Counterpart's flat-by-design engineering organization. Your focus will be on scaling impact through enhanced infrastructure, improved context systems, and leveraging agents to amplify every engineer's output. You will be responsible for the technical vision, engineering operations, and people strategy for the function, and you will represent Counterpart's technology strategy to the board.

Key Responsibilities

• Evolve the scaling strategy for a flat engineering organization using AI agents, ensuring high talent density and driving efficiency through AI. Set the forward-looking technical vision to support business objectives.
• Shape Counterpart's software development approach in an AI-native environment. Partner with the CEO, engineering leaders, and technical product managers to refine building processes, operational methods, and output compounding.
• Manage the Engineering function, allocating people and agents across various initiatives. Own allocation decisions, engineering standards, delivery quality, and the mechanisms to ensure technical coherence within independent project teams.
• Oversee the infrastructure supporting AI-native engineering, including developer experience, AI and data platforms, and core system infrastructure.
• Lead hiring, performance management, compensation, and talent development for the engineering organization. Collaborate with the Head of People and Chief of Staff to align Engineering's people model and operations with company operating cadences.
• Ensure 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.

Candidate Qualifications

• Extensive Leadership Experience: Over 12 years in engineering leadership, having guided engineering organizations through multiple company-stage transitions. Proven experience engaging with the board, investors, and executive leadership. Deep understanding of effective engineering organizational structures at various stages and common scaling challenges.
• AI-Native Engineering Vision: A strong perspective on what AI-native engineering entails beyond just using AI tools. Demonstrated deep thought on how AI transforms the engineer's role, engineering organization structure, and the economics of software delivery. Ability to articulate and defend opinions on industry direction, while discerning hype from reality.
• Technical Fluency: Profound technical understanding to form strong opinions on system architecture, AI and data infrastructure, and deployment pipelines.
• Customer Empathy and Product Sense: Ability to integrate business and technology considerations seamlessly. Continuously seeks to empower the business through technology, building new capabilities while enhancing underlying systems. A pragmatic approach to refactoring and feature delivery, ensuring robust foundations.
• Distributed Team Leadership: Experience leading fully distributed teams with a strong emphasis on trust and accountability.
• Regulated Industry Experience (Plus): Experience in regulated sectors such as insurance, fintech, or healthcare is highly desirable. Understanding that compliance (e.g., SOC 2, HIPAA, state cybersecurity regulations) should be built into systems, not added as an afterthought.

Meet the Team

You will collaborate closely with a dedicated leadership and engineering team, including:

• Tanner Hackett, CEO
• Tobias Schuler, Chief Underwriting Officer
• Kelly North, VP of Revenue
• Ali Fiedler, Head of People
• Chris Shafer, Chief of Staff
• Eric Marler, Head of Claims
• Dave Lin, Head of Product
• Ron Alexessen, Engineering Manager
• Chad Nierenhausen, Engineering Manager
• Jon Mendez, Engineering Manager
• Newton Troung, Engineering Manager
• Julian Prokay, Principal Engineer
• Derrick Franco, Principal Engineer
• Ben Nickerson, Technical Product Manager
• Natalie Anderson, Technical Product Manager
• Abhi Singh, Technical Product Manager

What Counterpart Offers

• Fully Remote Workplace: Work from anywhere globally, as Counterpart is a fully distributed company with no physical office. Team members meet in person a couple of times per year.
• Unlimited Vacation: Enjoy flexible time off whenever needed.
• Stock Options: Opportunity for equity ownership.
• Comprehensive Benefits: Health, Dental, and Vision Coverage.
• 401(k) Retirement Plan: Secure your financial future.
• Paid Parental Leave: Support for new parents.
• Home Office Allowance: Stipend to set up your ideal home office.
• Wellness Stipend: Support for your well-being.
• Learning Budget: Includes book stipend and professional development reimbursement.
• Birthday Off: Take your birthday as a paid day off to relax and celebrate.
• Charitable Contribution Matching: Counterpart matches employee donations to charitable organizations.

Commitment to Diversity and Inclusion

Counterpart is dedicated to fostering a welcoming and inclusive workplace for everyone. They actively ensure that all individuals feel respected, supported, and connected, regardless of background. The company values and celebrates differences, believing that openness enables individuals to perform their best work. Counterpart is an Equal Opportunity Employer and prohibits discrimination based on race, color, religion, gender identity, sex, sexual preference, sexual identity, pregnancy, national origin, ancestry, citizenship, age, marital status, physical disability, mental disability, medical condition, military status, or any other characteristic protected by federal, state, or local law.