The Challenge: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time-consuming. At Jerry.ai, we are building the first mobile app to manage it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store and we have more than 5 million users! About the Opportunity: You will lead the evolution of our AI-powered customer experience and internal AI platform. Your challenge will be to own one of the most strategic areas of the company: how we leverage large language models, agents, and internal APIs to deliver best-in-class, automated customer support and operations. You will sit at the intersection of product, engineering, and applied AI, and require both strategic thinking and hands-on exploration with modern LLM systems. You will build and scale a sophisticated AI system that already includes: - A production-grade conversational AI experience automating >70% of inbound sales and service over chat and SMS - Human-in-the-loop systems for chat evaluation, feedback, and continuous improvement - Internal process automation flows across the company, including automated image review and approval - Jerry.ai insurance and repair quotes available directly in the ChatGPT App, developed in partnership with OpenAI - You will also be responsible for constantly evaluating new models and AI capabilities. This includes evaluating emerging AI technologies, such as voice models and computer use agents, for suitability in a regulated production environment. How You'll Make an Impact: - Lead end-to-end product development for Jerry's AI-powered customer experiences and internal AI platform, from roadmap to rollout. - Partner with engineers and prompt engineers to design and iterate on AI architectures, prompt strategies, evaluation frameworks, and guardrails — making real tradeoffs between latency, cost, accuracy, and user experience. - Be the bridge between engineering and the rest of the org: lead by example for AI best practices and get other teams on board with platform standards. - Own the metrics that matter — answer quality, customer satisfaction, automation rate, escalation quality — and drive systematic improvement through data and experimentation. - Work directly with our partners at OpenAI to evaluate new models and capabilities, and identify the next big leaps in voice, computer use, and workflow automation. Who You Are: - You have 4+ years of experience in technical product management, management consulting, data analytics, or operations at a fast-paced startup. - You're passionate about AI and intrinsically motivated to get hands on with the latest technology. When a new model drops, you read the release notes. You've set up your own AI tools and workflows not because someone told you to, but because you couldn't help yourself. - You're a technologist and a systems thinker. You're comfortable in technical conversations about system architecture, API design, and prompt engineering, and you can translate complex ideas into simple terms for non-technical stakeholders. - You're data-driven, familiar with SQL, and comfortable diving into data to answer your own questions. - You like to own metrics and constantly seek improvement. You're an optimist who asks "how can we" not "if we can." While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

The Challenge: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time-consuming. At Jerry.ai, we are building the first mobile app to manage it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store and we have more than 5 million users! About The Opportunity: You will lead the evolution of our AI-powered customer experience and internal AI platform. Your challenge will be to own one of the most strategic areas of the company: how we leverage large language models, agents, and internal APIs to deliver best-in-class, automated customer support and operations. You will sit at the intersection of product, engineering, and applied AI, and require both strategic thinking and hands-on exploration with modern LLM systems. You will build and scale a sophisticated AI system that already includes: - A production-grade conversational AI experience automating >70% of inbound sales and service over chat and SMS - Human-in-the-loop systems for chat evaluation, feedback, and continuous improvement - Internal process automation flows across the company, including automated image review and approval - Jerry.ai insurance and repair quotes available directly in the ChatGPT App, developed in partnership with OpenAI You will also be responsible for constantly evaluating new models and AI capabilities. This includes evaluating emerging AI technologies, such as voice models and computer use agents, for suitability in a regulated production environment. How You'll Make an Impact: - Lead end-to-end product development for Jerry's AI-powered customer experiences and internal AI platform, from roadmap to rollout. - Partner with engineers and prompt engineers to design and iterate on AI architectures, prompt strategies, evaluation frameworks, and guardrails — making real tradeoffs between latency, cost, accuracy, and user experience. - Be the bridge between engineering and the rest of the org: lead by example for AI best practices and get other teams on board with platform standards. - Own the metrics that matter — answer quality, customer satisfaction, automation rate, escalation quality — and drive systematic improvement through data and experimentation. - Work directly with our partners at OpenAI to evaluate new models and capabilities, and identify the next big leaps in voice, computer use, and workflow automation. Who You Are: - You have 4+ years of experience in technical product management, management consulting, data analytics, or operations at a fast-paced startup. - You're passionate about AI and intrinsically motivated to get hands on with the latest technology. When a new model drops, you read the release notes. You've set up your own AI tools and workflows not because someone told you to, but because you couldn't help yourself. - You're a technologist and a systems thinker. You're comfortable in technical conversations about system architecture, API design, and prompt engineering, and you can translate complex ideas into simple terms for non-technical stakeholders. - You're data-driven, familiar with SQL, and comfortable diving into data to answer your own questions. - You like to own metrics and constantly seek improvement. You're an optimist who asks "how can we" not "if we can." While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

• Lead a team of engineers, researchers, and data scientists, performing QA on AI agent outputs • Evaluate RAG pipeline architectures, challenge prompt engineering decisions, and review system designs • Build relationships with internal business teams, understanding workflows and translating pain points into actionable technical work • Set priorities and decide what the team works on across both AI Enablement and AI Experiments tracks • Serve as the primary liaison with internal business teams, gather requirements, and validate priorities • Communicate progress clearly to leadership and identify new internal processes where AI could reduce effort • Guide the team’s technology roadmap, evaluate architecture decisions and optimize AI infrastructure spend

Role Description We are seeking a strategic and detail-oriented Product Manager to join our team. As a key link between business stakeholders and the development team, you will be responsible for defining and prioritizing product requirements, managing the product backlog, and ensuring successful delivery of high-quality software that aligns with our strategic goals. What You’ll Do: Product Ownership & Vision: - Serve as the voice of the customer and business in the development process. - Translate product vision and strategy into actionable user stories and requirements. - Define and clearly communicate the product roadmap and priorities to internal teams. Backlog Management: - Own and manage the product backlog: prioritize features, bugs, and technical debt. - Write detailed and clear user stories, acceptance criteria, and workflows. - Collaborate closely with developers, designers, QA, and other stakeholders. Stakeholder Collaboration: - Work with business units, sales, marketing, and support teams to gather feedback and define needs. - Regularly update stakeholders on progress, timelines, and changes to scope. Delivery & Quality: - Participate in sprint planning, reviews, retrospectives, and daily stand-ups. - Make decisions on scope and prioritization to ensure timely delivery. - Ensure the delivered product meets functional and non-functional requirements. Travel Requirement: Approximately 10-15% travel may be required. Duties, responsibilities, and activities may change at any time with or without notice, in accordance with applicable laws. Qualifications - 3+ years of experience as a Product Owner or in a similar role in an Agile environment. - Strong understanding of Agile/Scrum methodologies. - Proven ability to translate business needs into technical requirements. - Excellent communication, problem-solving, and organizational skills. Preferred: - Certified Scrum Product Owner (CSPO) or equivalent. - Experience with tools like Jira, GitHub, Azure DevOps, or similar. - Background in software development, UX, or QA. - Experience working in B2B software environments or the automotive industry. Requirements - Strategic thinking with a focus on delivering business value. - User-centric mindset. - Detail-oriented with the ability to manage multiple priorities. - Ability to lead by influence and build strong cross-functional relationships. - Data driven and evidence-based decision making. Benefits - Medical, dental, and vision insurance. - 401(k) with company match. - Paid time off and holidays. Work Environment & Physical Requirements - This role may be performed in a remote, hybrid, or office-based environment depending on business needs. - Ability to remain in a stationary position (sitting or standing) for extended periods. - Ability to operate a computer and standard office equipment (e.g., keyboard, mouse, headset). - Ability to view and interpret information on a computer screen for extended periods. - Ability to communicate effectively via phone, video, and written communication. - Ability to participate in virtual meetings with or without reasonable accommodation. Remote Work Expectations - Maintain a dedicated, safe, and distraction-free workspace. - Reliable high-speed internet connection sufficient for video conferencing and job-related systems. - Ability to maintain productivity in a remote environment. Travel - Ability to travel as needed, including by air, car, or public transportation. Additional Information - Reasonable accommodations may be made to enable individuals with disabilities to perform essential job functions. - Employment may be contingent upon a background check in accordance with applicable laws. Note: This job description is intended to outline the general responsibilities and requirements of the role. It is not an exhaustive list of all duties, tasks, or responsibilities that may be required. Responsibilities and priorities may evolve over time, and the company reserves the right to make changes at any time with or without notice. Vehlo is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws. This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. Vehlo makes hiring decisions based solely on qualifications, merit, and business needs at the time.