VP of Engineering

VP of Engineering Counterpart believes in small businesses and is dedicated to helping them do more with less risk. By pairing leading insurance experts with cutting-edge technology, Counterpart empowers small business owners to grow with confidence. Exceptional underwriters, trusted insurance brokers, and prominent insurance carriers come together on the Counterpart platform to support small businesses by providing AI-driven management and professional liability underwriting and claims services. That’s where you come in… 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. As VP of Engineering, you will: 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. YOU HAVE: 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. WHO YOU’LL WORK WITH: 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 WE OFFER 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 We are committed to being a welcoming and inclusive workplace for everyone, and we are intentional about making sure people feel respected, supported and connected at work—regardless of who you are or where you come from. We value and celebrate our differences and we believe being open about who we are allows us to do the best work of our lives. We are an Equal Opportunity Employer. We do not discriminate against qualified applicants or employees on the basis of 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, rule, or regulation.