Senior Product Manager, AI Agents and Platform

🏢 Summary: Lead the end-to-end development of an AI platform leveraging LLMs, agents, and internal APIs to automate customer interactions and sales workflows at scale. The role focuses on designing prompt strategies, evaluation frameworks, and AI guardrails while driving experimentation to improve automation, quality, and customer satisfaction. You will collaborate with engineering and OpenAI partners to deploy advanced voice models and workflow automation in production. 🗂️ Requirements: 4+ years in management consulting or technical product management at a fast-paced startup, Proven experience with modern LLM systems, Experience designing AI-driven products in production environments, Ability to design API strategies and system architectures, Experience creating prompt strategies and evaluation frameworks, Ability to analyze data using SQL, Experience leading AI platform standards and best practices, Track record of delivering scalable, production-grade AI products 📃 Skills: LLMs, APIs, SQL, OpenAI, Prompting, Automation, Agents, Voice, Architecture, Experimentation 🏢 Description: Why Jerry.ai?We are building the first super app to manage car ownership—an industry where the experience is stuck in the 90s.Lead a strategic area leveraging LLMs, agents, and internal APIs to automate a fragmented, $2T market.Work with partners at OpenAI to integrate Jerry.ai services directly into the ChatGPT App and pioneer new model capabilities. Lead the AI Revolution for Jerry.ai:At Jerry.ai, we are moving past fragmented, time-consuming processes to create a seamless, automated platform.You will sit at the intersection of product, engineering, and applied AI as you build and scale a sophisticated system that already automates >70% of inbound sales and service requests (over 50k chats per month). Your role will include shaping how modern LLM systems, human-in-the-loop feedback, and computer-use agents redefine an entire industry. How You Will Make an Impact:Lead end-to-end development for our AI platform and customer experiences, from initial roadmap to rollout.Partner with engineers to design prompt strategies, evaluation frameworks, and guardrails—balancing latency, cost, and accuracy.Serve as the technical translator between engineering and the broader organization, establishing AI best practices and platform standards.Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation.Work with partners at OpenAI to evaluate and deploy the next generation of voice models and workflow automation. What We’re Looking For in a Builder:Intrinsically Motivated Technologist: You live and breathe AI. You read the release notes when a new model drops and you’ve already built your own custom workflows.Systems Thinker: You are comfortable diving into technical conversations about API design and system architecture, translating complex concepts for any audience.Optimistic Problem-Solver: You are a "how can we" thinker who seeks constant improvement and thrives on owning high-impact metrics.Data-Driven with Conviction: You are familiar with SQL and comfortable diving into the data to answer your own questions and validate hypotheses. Ideal Profile:4+ years of experience in management consulting or technical product management at a fast-paced startup.Proven interest in modern LLM systems.Ability to navigate technical tradeoffs and lead by example when implementing AI platform standards.A track record of taking complex, strategic ideas and turning them into scalable, production-grade products.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.aiThe 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.aiJerry.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.Compensation Range: $160K - $200K

🏢 Summary: Lead the end-to-end development and scaling of an AI platform that leverages LLMs, agents, and internal APIs to automate customer sales and service workflows. Drive prompt design, evaluation frameworks, guardrails, and experimentation to improve automation, quality, and customer satisfaction. Collaborate with engineering and OpenAI partners to deploy next-generation voice models and workflow automation. 🗂️ Requirements: 4+ years in management consulting or technical product management at a fast-paced startup, Proven experience with modern LLM systems, Ability to design and discuss API architecture and system design, Experience implementing AI platform standards and best practices, Strong SQL skills for data analysis and hypothesis validation, Experience building and scaling production-grade AI products, Ability to evaluate technical tradeoffs in AI systems 📃 Skills: LLMs, APIs, SQL, OpenAI, Prompting, Automation, Architecture, Experimentation, Voice, Agents 🏢 Description: Why Jerry.ai?We are building the first super app to manage car ownership—an industry where the experience is stuck in the 90s.Lead a strategic area leveraging LLMs, agents, and internal APIs to automate a fragmented, $2T market.Work with partners at OpenAI to integrate Jerry.ai services directly into the ChatGPT App and pioneer new model capabilities. Lead the AI Revolution for Jerry.ai:At Jerry.ai, we are moving past fragmented, time-consuming processes to create a seamless, automated platform.You will sit at the intersection of product, engineering, and applied AI - building and scaling a sophisticated system that already automates >70% of inbound sales and service requests (over 50k chats per month). Your role will include shaping how modern LLM systems, human-in-the-loop feedback, and computer-use agents redefine an entire industry. How You Will Make an Impact:Lead end-to-end development for our AI platform and customer experiences, from initial roadmap to rollout.Partner with engineers to design prompt strategies, evaluation frameworks, and guardrails—balancing latency, cost, and accuracy.Serve as the technical translator between engineering and the broader organization, establishing AI best practices and platform standards.Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation.Work with partners at OpenAI to evaluate and deploy the next generation of voice models and workflow automation. What We’re Looking For in a Builder:Intrinsically Motivated Technologist: You live and breathe AI. You read the release notes when a new model drops and you’ve already built your own custom workflows.Systems Thinker: You are comfortable diving into technical conversations about API design and system architecture, translating complex concepts for any audience.Optimistic Problem-Solver: You are a "how can we" thinker who seeks constant improvement and thrives on owning high-impact metrics.Data-Driven with Conviction: You are familiar with SQL and comfortable diving into the data to answer your own questions and validate hypotheses. Ideal Profile:4+ years of experience in management consulting or technical product management at a fast-paced startup.Proven interest in modern LLM systems.Ability to navigate technical tradeoffs and lead by example when implementing AI platform standards.A track record of taking complex, strategic ideas and turning them into scalable, production-grade products.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.aiThe 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.aiJerry.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.Compensation Range: $160K - $200K

🏢 Summary: Lead the end-to-end development of a customer-facing Agentic AI platform leveraging LLMs, internal APIs, and computer-use agents to automate sales and service experiences at scale. Own the roadmap, prompt strategy, evaluation frameworks, and AI platform standards while partnering with engineering and OpenAI to deploy next-generation voice and workflow automation models. Drive experimentation and data-backed improvements to increase automation, answer quality, and customer satisfaction. 🗂️ Requirements: 4+ years in a technical role (e.g., forward deployed engineering, technical product management), Hands-on experience with LLMs and AI systems, Experience designing API architectures and system integrations, Ability to design prompt strategies, evaluation frameworks, and guardrails, Experience running experiments and improving systems through data analysis, Proficiency in SQL, Track record of delivering scalable, production-grade AI products 📃 Skills: LLMs, APIs, SQL, OpenAI, Automation, Voicebots, Agents, MachineLearning 🏢 Description: Why Jerry.ai? Join a pre-IPO startup with capital ($240M raised), traction (5M+ customers), and runway (we’re profitable). Impact: Come lead our customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs to create a magical experience for our customers. Work with partners like OpenAI to integrate services directly into the ChatGPT App and pioneer new model capabilities. Accelerated career growth. Flat org chart, ambitious goals, and significant ownership. You’ll report directly to the COO, leading one of the most important growth levers. Why we’re hiring this role: Your car and your home are your most important assets, yet the experience of owning one is fragmented, complicated, and expensive. We are building the first app to manage it all. We launched car insurance in 2019 and became one of the top three brokers in the country, partly by being early adopters of generative AI. Before off-the-shelf platforms existed, we built our own infrastructure to automate sales and service conversations. Today, that system handles a meaningful share of customer interactions end-to-end. The underlying technology is entirely homegrown. Prompts powering the customer-facing chatbot, vehicle photo validation, and back-office automation live across multiple locations with no unified platform or single source of truth. There is no clear owner of major future bets such as voicebot, computer use, and consumer AI applications. This role will own that vision and execution. How you’ll make an impact: - Lead end-to-end development for the AI platform and customer experiences, from roadmap to rollout. - Partner with engineers to design prompt strategies, evaluation frameworks, and guardrails, balancing latency, cost, and accuracy. - Serve as the technical translator between engineering and the broader organization, establishing AI best practices and platform standards. - Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation. - Work with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation. Who you are: - Technologist deeply engaged with AI and modern LLM systems. - Systems thinker comfortable with API design and system architecture. - Experimenter constantly exploring new AI capabilities. - Data-driven and proficient in SQL for analysis and validation. - Pragmatic in navigating technical tradeoffs and setting platform standards. Ideal experience: - 4+ years in a technical role such as forward deployed engineering or technical product management at a fast-paced startup. - Passion for AI systems including modern LLMs. - Track record of turning complex strategic ideas into scalable, production-grade products. Compensation: Base salary range: $160K - $200K. Compensation may include equity grants. Benefits: Comprehensive benefits package including health, dental, and vision coverage, paid time off, paid parental leave, 401(k) with employer matching, and wellness benefits. Equity opportunities may be included as part of total rewards.

🏢 Summary: Jerry.ai is hiring an Organic Growth Lead to own SEO and Answer Engine Optimization strategy, leading AI-powered content production and editorial standards for insurance and automotive-related content. The role focuses on building scalable content systems that rank on search engines and earn citations from AI platforms like ChatGPT and Gemini while driving customer acquisition. 🗂️ Requirements: Bachelor’s degree, Experience with SEO and AEO content strategy, Ability to build and manage AI-powered content workflows, Strong editorial and content quality judgment, Experience using LLMs for drafting, research, and automation, Knowledge of AI answer engines and content discovery systems, Ability to enforce factual accuracy and sourcing standards, Must reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada 📃 Skills: SEO, AEO, LLMs, ChatGPT, Claude, Gemini, Perplexity, AI, QA, Analytics, Automation 🏢 Description: Why We Exist Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top three brokers in the country, then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, scaled revenue 70x, and became profitable in early 2024. Why We're Hiring Content is how millions of people find us. Every article, guide, and FAQ we publish either earns a click, a citation, and a customer, or diminishes our online reputation. The discovery landscape is rapidly evolving. Ranking on Google search is no longer the only thing that matters. When someone asks ChatGPT or Claude how to lower their car insurance after an accident, we want to show up in the answer they get. Most brands that rely on trust and reputation (e.g. financial services, insurance, healthcare, etc) haven't yet figured out how to win in AEO (Answer Engine Optimization). We intend to be among the first. We're hiring an Organic Growth Lead to lead Jerry's content quality and output (on jerry.ai and on external platforms), and to build and lead the system that makes us authoritative everywhere our customers look for answers. Why You Will (Or Won't) Like Working Here Lean team. You will have one direct report, AI agents, and a freelance bench. The editorial output is dictated by you, and you will set the bar through your own work. The metric is customers converted, not page views. You will own traffic and AI-citation targets that directly impact top and bottom line growth, not page visits or impressions. We are rebuilding our AI-native content system. You will design and operate the brief-to-publish pipeline including LLM prompts, QA gates, human-edit checkpoints, and be accountable for what ships. Insurance content has a zero-tolerance accuracy standard. YMYL finance content cannot be "close enough." Every factual claim needs sourcing; every edge case needs verification. AI drafts require genuine human judgment to clear the bar, not a light read. What You'll Own How customers find us on Google and LLMs: Build content that ranks on Google and earns citations in ChatGPT, Perplexity, and Gemini about insurance, maintenance, or repairs. Figure out how to structure pages so AI answer engines surface Jerry's answers. Extend that visibility by staying on top of how SEO & AEO developes, to make sure that your content puts Jerry in front of people who've never been to jerry.ai. Track where Jerry shows up and where it doesn't, and close the gaps. Content strategy: Own Jerry's editorial engine across jerry.ai and external channels — what we publish, where, and why — with organic traffic and customer acquisition targets attached. Set the roadmap and defend resource allocation against competing priorities. AI-powered content production: Design and operate a content production system built to scale: brief → AI draft → human edit → QA → publish. Build the quality controls and drift metrics that prevent output from degrading as volume grows. The call on what AI handles and where a human stays in the loop is yours to make. Credibility at scale: Set and enforce Jerry's editorial standards across writers and AI agents. Content that touches someone's insurance or financing decision carries real credibility requirements — named authors, sourced claims, transparent review processes. Build that infrastructure and hold it. What You Bring Editorial taste. You understand that there’s a million ways to say the same thing and that every word matters. You have an eye for writing that is both engaging and compelling, and that works for both humans and LLMs. Insatiable desire to learn. This role requires mastery over domains that are rapidly and constantly evolving (e.g. how answer engines like ChatGPT, Gemini, Claude, Perplexity, or others find, evaluate and surface information to users, how information suppliers like Jerry.ai can optimize discovery of our content, etc.) Passion for AI. You’re an LLM power user. You know how to expertly wield it to draft, research, synthesize, automate, and amplify your impact. Bachelor’s degree. 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. We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto. Compensation Range: $150K - $190K

🏢 Summary: Lead the strategy and evolution of a customer-facing Agentic AI platform, consolidating prompts, optimizing chatbot prioritization, and driving architectural decisions across LLM-powered systems. Own emerging AI initiatives such as voicebot and computer use, while managing integrations with OpenAI and internal tools. Work hands-on with prompt engineering and cross-functional teams to scale production-grade AI products. 🗂️ Requirements: 3+ years in a technical role (e.g., forward deployed engineering, technical product management) in a fast-paced startup, Experience with modern LLMs and AI systems, Ability to design and discuss API architecture and system design, Experience building scalable, production-grade AI products, Proficiency in SQL for data analysis, Hands-on experience with prompt engineering, Ability to manage technical prioritization and platform strategy 📃 Skills: LLMs, OpenAI, SQL, APIs, Prompting, GitHub, Replit, CRM, Voicebot, AI 🏢 Description: Why Jerry.ai? Join a pre-IPO startup with significant capital raised, strong customer traction, and profitability. Lead our customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs to create a seamless experience for customers. Work with partners like OpenAI to integrate services directly into the ChatGPT App and pioneer new model capabilities. You will report directly to the COO and drive one of the company’s most important growth levers. Why we’re hiring this role: Owning a car or home is fragmented, complicated, and expensive. We are building the first app to manage the entire journey — buy/sell, insurance, maintenance, and repairs. We were early adopters of generative AI, building in-house infrastructure to automate sales and service conversations, which now handles a significant share of customer interactions end-to-end. However, prompts and AI workflows are distributed across multiple systems with no unified platform or ownership. This role will own consolidation, strategy, and future AI investments including voicebot and computer use. How you’ll make an impact: Your scope covers maintaining the current AI platform while driving architectural decisions for its future state. In the first few months you will: - Learn and contribute to the prompt engineering workflow - Write and update prompts - Understand how tech stacks such as Propelix, Botly, CRM, GitHub, and Replit interact - Identify system bottlenecks You will then own: - Prompt consolidation strategy and migration to a unified platform - Technical prioritization of chatbot initiatives - Coordination across engineering, data, and operations - Evaluation and investment decisions in emerging technologies such as voicebot and computer use - Relationship with OpenAI and presence in the ChatGPT store Who you are: - Technologist deeply engaged with AI advancements and model releases - Systems thinker comfortable with API design and architecture discussions - Experimenter continuously exploring new AI capabilities - Data-driven and proficient in SQL - Pragmatic in navigating technical tradeoffs and setting AI platform standards Ideal experience: - 3+ years in a technical role such as forward deployed engineering or technical product management at a fast-paced startup - Passion for AI systems and modern LLMs - Proven ability to turn complex strategic ideas into scalable, production-grade products Compensation and Benefits: Compensation range: $130K - $170K. Total rewards may include equity grants. Comprehensive benefits include health, dental, and vision coverage, paid time off, paid parental leave, 401(k) with employer matching, and wellness benefits.

🏢 Summary: Lead the development and scaling of a customer-facing Agentic AI platform using LLMs, APIs, and workflow automation to improve sales and service experiences. The role focuses on building AI systems, defining prompt and evaluation strategies, and collaborating with engineering and AI partners to deploy advanced automation and voice models. Candidates should have experience in technical product or engineering roles and strong expertise in modern AI systems and data-driven experimentation. 🗂️ Requirements: 4+ years in a technical role such as forward deployed engineering or technical product management, Experience with AI systems and modern LLMs, Ability to design and scale production-grade AI products, Knowledge of API design and system architecture, Experience translating technical concepts across teams, SQL proficiency, Experience with experimentation and evaluation frameworks, Ability to balance latency, cost, and accuracy in AI systems, Must currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada 📃 Skills: LLMs, SQL, APIs, AI, Automation, Voicebot, Architecture, Prompting, Experimentation, Chatbots 🏢 Description: Why Jerry.ai? Join a pre-IPO startup with capital ($240M raised), traction (5M+ customers), and profitability. Impact Come lead our customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs to create a customer experience. Work with partners like OpenAI to integrate services directly into the ChatGPT App and pioneer new model capabilities. Accelerated career growth The organization has a flat structure, ambitious goals, and opportunities for growth. This role reports directly to the COO and leads a major growth initiative. Why this role exists The company is building an app to manage car and home ownership across buying, insurance, maintenance, repairs, and selling. Existing AI infrastructure already automates a large share of customer interactions, but prompt systems and AI workflows are fragmented across multiple systems. This role will own the roadmap and platform direction for future AI initiatives including voicebots, computer-use agents, and consumer AI applications. How you’ll make an impact - Lead end-to-end development for the AI platform and customer experiences, from roadmap to rollout - Partner with engineers to design prompt strategies, evaluation frameworks, and guardrails balancing latency, cost, and accuracy - Establish AI best practices and platform standards across the organization - Drive improvements in answer quality, customer satisfaction, and automation rates through experimentation - Work with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation Who you are - Technologist with strong interest in AI systems and modern models - Systems thinker comfortable with API design and system architecture - Experimenter who continuously explores emerging AI capabilities - Data-driven and comfortable using SQL to analyze data and validate hypotheses - Pragmatic in navigating technical tradeoffs and implementing standards Ideal experience - 4+ years of experience in a technical role such as forward deployed engineering or technical product management at a fast-paced startup - Passion and curiosity for AI systems including modern LLMs - Track record of turning strategic concepts into scalable, production-grade products Benefits and compensation - Competitive compensation with potential equity grants - Health, dental, and vision coverage - Paid time off and paid parental leave - 401(K) plan with employer matching - Wellness benefits - Fully remote environment with offices in Palo Alto, New York, Chicago, and Toronto - Salary range: $160K - $210K

🏢 Summary: Senior Editor-in-Chief role focused on building and scaling an AI-native content operation for insurance and personal finance topics. The position owns SEO, AEO, editorial quality, AI-assisted publishing workflows, and organic growth targets across search and AI answer engines. The role combines hands-on editorial leadership with management of AI-driven content systems and compliance for high-accuracy YMYL content. 🗂️ Requirements: 7+ years in content and editorial roles, 3+ years leading SEO-driven content programs, Experience with AI-assisted content pipelines in production, Experience in regulated or high-stakes content categories, Hands-on use of LLMs for drafting and research, Fluency with SEO analytics and traffic reporting tools, Experience managing writers or freelance contributors, Portfolio demonstrating editorial judgment and accuracy 📃 Skills: SEO, AEO, LLMs, ChatGPT, Claude, Gemini, Semrush, Ahrefs, GA4, GSC, Surfer, Clearscope, MarketMuse, Frase, Sitefire 🏢 Description: Why We Exist Your car and your home are your most important assets, yet the experience of owning them is fragmented, complicated, and expensive. Jerry.ai is building an app to manage insurance, repairs, financing, and maintenance. We started with car insurance in 2019, became one of the top three brokers in the country, then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, scaled revenue 70x, and became profitable in early 2024. Why We're Hiring Content is how millions of people find Jerry. Every article, guide, and FAQ published either earns a click, citation, and customer, or diminishes online reputation. The discovery landscape is evolving rapidly. Ranking on Google search is no longer the only priority. The company aims to appear in answers generated by AI tools such as ChatGPT and Claude and become an early leader in AEO (Answer Engine Optimization). The company is hiring an Editor-in-Chief to lead content quality and output across platforms and build the system that establishes authority wherever customers seek answers. Why You Will Like Working Here - Lean editorial team with one direct report, AI agents, and freelance contributors - Editorial output and quality standards owned by the Editor-in-Chief - Success measured by customer conversions, traffic, and AI citations - Ownership of AI-native content workflows including prompts, QA gates, and publishing systems - High editorial accuracy standards for YMYL finance and insurance content What You'll Own Content strategy: - Own the editorial engine across company platforms - Define roadmap, architecture, resource allocation, and traffic/conversion targets - Develop strategy and execute measurable growth goals AI-native production: - Design and manage AI-assisted workflows from brief to publish - Build prompt libraries, QA gates, and quality-drift metrics - Define where AI is used and where human oversight is required SEO, AEO, and off-domain authority: - Build content clusters that rank on Google and earn citations from AI answer engines - Structure content using answer capsules, question-based headings, FAQ schema, and entity optimization - Track citation visibility and improve performance across AI platforms E-E-A-T and YMYL compliance: - Maintain editorial voice and style guidelines - Establish sourcing discipline, editorial review processes, and transparent credentials - Ensure accuracy standards for regulated finance content Who You Are - Strong writer and editor capable of improving AI-generated drafts - Systems-oriented thinker comfortable with workflows, templates, and QA checkpoints - Experienced in shipping AI-assisted content systems in production - Practitioner of AEO with knowledge of AI answer engine optimization - Experienced in regulated content categories such as insurance, finance, healthcare, or legal What You'll Bring - 7+ years in content and editorial roles - 3+ years leading SEO-driven content programs in consumer, fintech, insurtech, marketplace, media, or affiliate environments - Proven organic growth achievements with measurable results - Hands-on command of ChatGPT, Claude, Gemini, and SEO/content tools including Sitefire, Surfer, Clearscope, MarketMuse, or Frase - Fluency in GSC, Semrush or Ahrefs, and GA4 - Experience managing writers or freelance contributors while producing content personally - Portfolio demonstrating editorial judgment, voice, and accuracy Additional Information - Remote hiring limited to candidates residing in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada - Compensation range: $150K - $190K - Benefits include health, dental, vision, paid time off, paid parental leave, 401(k) matching, wellness benefits, and potential equity grants

🏢 Summary: Data Science & Analytics role embedded within core business units (growth, product, AI & automation, strategic partnerships), responsible for defining business problems, building analyses and experiments, and driving data-informed decisions to scale the company from 5M to 50M customers. The position combines strategic thinking with hands-on execution, owning metrics, insights, and end-to-end analytical impact. Candidates will influence leadership decisions through rigorous analysis and clear communication. 🗂️ Requirements: 2+ years experience in consulting, investment banking, or high-growth technology company, Strong analytical skills with ability to independently pull, structure, and interpret data, Proficiency in SQL or Python, Experience owning ambiguous problems and delivering measurable impact, Ability to influence leadership through clear, persuasive communication 📃 Skills: SQL, Python, Clickhouse, Metabase, Jupyter, GitHub 🏢 Description: Why We Exist Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive. Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024. We're now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets. Why We’re Hiring Our Data Science & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team who drive data & insights, and inform decision-making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations. Every business unit has a Data Science team member embedded within it — someone who doesn't just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years. As our business continues to expand, there is growing demand for more Data Science team members. We are hiring 4-6 people to drive impact in these areas: - Growth Marketing - Product Development - AI & Automation - Strategic Partnerships On leveling: You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling. Why You Will (Or Won't) Like Working Here No slides: The only work that gets done is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, or a critical partner relationship. No corporate fluff: The Data Science & Analytics team cares deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals. Hands-on: This is not a pure strategy role, you will also own execution. Your day-to-day will be surfacing analytical insights, driving decisions, and seeing them through end-to-end. What You'll Own You'll sit on our central Data Science & Analytics team but be embedded in one of Jerry's core business areas — growth, product, AI and automation, or strategic partnerships — and own the analytical function for that business unit end-to-end. Define the right problems: Before any analysis, understand what business question it's answering and what decision it will inform. Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics. Drive outcomes: Bring recommendations to counterparts in product, growth, finance, or operations, explain what's happening and why, and define next steps. Who You Are First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You're analytically strong and comfortable with SQL or Python. Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy-in quickly. You write clearly and speak precisely. Owner: You take responsibility for fixing problems, even outside your immediate scope. What You'll Bring 2+ years of experience at a consulting firm, investment bank, or high-growth technology company. Strong analytical skills; ability to pull, structure, and interpret data independently. Track record of owning ambiguous problems and delivering impact. Clear, persuasive communicator who can influence decisions at the leadership level. Our Tools SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub. Compensation Range: $130K - $150K

🏢 Summary: Lead the strategy and architecture of a customer-facing Agentic AI platform, consolidating prompts and driving integration of LLMs, voicebots, and emerging AI capabilities. Own technical prioritization, platform standards, and partnerships (including OpenAI) while ensuring the current AI systems operate reliably. This role blends hands-on prompt engineering with long-term AI platform strategy in a fast-paced startup environment. 🗂️ Requirements: 4+ years in a technical role (e.g., forward deployed engineering, technical product management), Experience with AI systems and modern LLMs, Ability to design and discuss API and system architecture, Experience building scalable, production-grade products, Proficiency in SQL for data analysis, Experience working in fast-paced startup environments 📃 Skills: LLMs, Prompting, APIs, SQL, GitHub, Replit, CRM, Voicebot, AI, MachineLearning 🏢 Description: Why we’re hiring this role: Your car and your home are your most important assets, yet the experience of owning one is fragmented, complicated, and expensive. We are building the first app to manage it all. We launched car insurance in 2019 and became one of the top three brokers in the country, in part by being early adopters of generative AI. Before off-the-shelf platforms existed, we built our own infrastructure to automate sales and service conversations. Today, that system handles a meaningful share of customer interactions end-to-end, and the underlying technology is entirely homegrown. As the system evolved, prompts powering the customer-facing chatbot, vehicle photo validation, and back-office automation now live across six separate locations. There is no single source of truth, no unified platform, and no clear owner of future AI bets such as voicebot, computer use, and consumer AI applications. This role owns that challenge. How you’ll make an impact: Your scope covers two layers: maintaining the current AI platform while driving architectural decisions that determine its future state. In the first few months, you will learn the prompt engineering workflow by writing and updating prompts, understanding how various tech stacks (e.g., Propelix, Botly, CRM, GitHub, and Replit) interact, and identifying bottlenecks. After that, you will own the platform strategy: - Prompt consolidation: Define and execute the strategy to migrate prompts from six locations to a unified platform, aligning engineering, data, operations, and other teams. - Chatbot prioritization: Own the technical prioritization queue and keep the team coordinated without unnecessary process overhead. - Emerging technology decisions: Track advancements in voicebot and computer use, determine when to invest, own the OpenAI relationship, and manage presence in the ChatGPT store. Influence AI investment decisions with a clear point of view. Who you are: - Technologist: Deep interest in AI, actively following new model releases and building custom workflows. - Systems Thinker: Comfortable discussing API design and system architecture and translating complex concepts for varied audiences. - Experimenter: Continuously exploring new AI capabilities. - Data-Driven: Proficient in SQL and comfortable analyzing data to validate hypotheses. - Pragmatic: Able to navigate technical tradeoffs and implement AI platform standards. Ideal experience: - 4+ years in a technical role such as forward deployed engineering or technical product management in a fast-paced startup. - Passion and curiosity for AI systems including modern LLMs. - Proven track record of turning complex strategic ideas into scalable, production-grade products. Compensation and Benefits: The starting pay range for this role is $160K - $200K, determined by skills, experience, qualifications, work location, and market conditions. Compensation may include equity grants. Benefits for regular employees include health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits. Equity opportunities may also be part of the total rewards package.

🏢 Summary: Senior platform product role owning the AI infrastructure powering multi-agent banking assistants across voice and digital channels. Responsible for defining technical direction, model lifecycle, orchestration, performance, safety, and platform contracts to scale to millions of users. Acts as a senior IC setting standards for AI-native, enterprise-grade, multi-tenant systems. 🗂️ Requirements: 8+ years product management experience, 3+ years at Staff/Principal level on platform, AI/ML, or infrastructure products, Experience owning multi-component platform used by multiple product teams, Ability to read code, review architecture, and debug production issues, Experience with LLM orchestration, evaluation, and fine-tuning pipelines, Experience defining and governing APIs, versioning, and platform contracts, Experience in enterprise SaaS with multi-tenant and compliance requirements, Knowledge of inference optimization and latency management for real-time systems 📃 Skills: LLM, RAG, RLHF, RLAIF, APIs, ASR, TTS, Python, Quantization, Encryption, SOC2, GDPR, Cursor, Copilot 🏢 Description: Banking is being reimagined—and customers expect every interaction to be easy, personal, and instant. We are building a universal banking assistant that millions of U.S. consumers can use to transact across all financial institutions and, over time, autonomously drive their financial goals. Powered by our proprietary BankGPT platform, this assistant is positioned to displace age-old legacy systems within financial institutions and own the end-to-end CX stack, unlocking a $200B opportunity and potentially replacing multiple publicly traded companies. Ultimately, our mission is to drive financial well-being for millions of consumers. With over two-thirds of Americans living paycheck to paycheck, 50% holding less than $500 in savings, and only 17% financially literate, we aim to put financial well-being on autopilot to help solve this problem.Company: interface.ai Location: Palo Alto, CA (In-Office) Reports to: VP of Product Compensation: $250,000 - $320,000 base salary + bonus + equity (depending on location & experience) About interface.ai Banking hasn't kept up with how people actually live their financial lives. At interface.ai, we're building AI-native products that transform how millions of Americans interact with their financial institutions, making every interaction intelligent, personal, and proactive.Our platform powers AI agents that handle real banking tasks end-to-end: moving money, resolving issues, converting loans, and surfacing financial insights across voice, chat, and digital channels. We're not building another chatbot. We're building the AI infrastructure that will become the primary way people bank, unlocking a massive market opportunity by displacing the legacy systems that financial institutions have been stuck with for decades. With two-thirds of Americans living paycheck to paycheck, only 17% financially literate, and 50% holding less than $500 in savings, the urgency is real. We're putting financial well-being on autopilot. We power AI agents for 100+ financial institutions, serving millions of banking members across the U.S., and are backed by leading investors including Avataar Venture Partners and Blume Ventures. Our platform enables banks and credit unions to automate high-volume customer interactions across voice and digital channels while improving resolution rates, reducing operational costs, and increasing customer engagement. Key credibility anchors: Series B AI company building agentic AI infrastructure for financial institutions Trusted by 100+ banks and credit unions across North America Serving millions of end users through conversational AI across voice, chat, and mobile channels The Opportunity You will own the AI platform that every product at the company depends on. This is not a support function: the platform is the competitive moat. Your decisions directly determine the ceiling of what every other product team can build. You'll inherit a multi component platform, assess what exists, and define what comes next: what to consolidate, what to invest in, what to sunset. As the senior IC in a pillar of 3-4PMs, you'll set technical direction, mentor, and raise the quality bar, while partnering with engineering leadership to scale the system to millions of end users at startup speed. What You'll Own Agent runtime & orchestration: multi-agent orchestration, memory/context management, tool routing, goal planning, and policy-aligned behavior Platform contracts: APIs, versioning, deprecation, and migration strategy: you define the boundaries and the lifecycle for all consuming teams Model lifecycle: selection, evaluation, benchmarking, fine-tuning enablement, and prompt optimization. You define when to prompt-tune vs fine-tune vs switch models. Inference performance & reliability: latency budgets, caching, batching, quantization, multi-region deployments, fallbacks, and safe rollout patterns (canaries, feature flags, rollback) Safety & compliance: PII detection/masking, prompt/response safety policies, tenant isolation, SOC2/GDPR readiness, audit logs, and encryption: compliance is a product requirement, not an afterthought Evaluation & quality: offline golden sets, regression testing, hallucination measurement, task success metrics, and production-to-improvement feedback loops Voice & multimodal: ASR/TTS integration patterns, WER, interruption handling, turn-taking, and latency budgets for real-time conversational intelligence Pillar leadership: You set technical direction, mentor, raise the bar, and have input on hiring. You prioritize competing demands from multiple product pillars, define the platform investment thesis, and protect the platform from becoming a feature factory. Who You Are You think in systems, not features. You read a platform outage postmortem and immediately see the product decision that caused it. You've built API contracts that entire product orgs depend on, and you've made the hard call to break one when the platform needed to evolve. You understand the full AI stack: from model training through inference optimization to production monitoring. You can spec a fine-tuning pipeline, set latency budgets for real-time voice, and debate quantization trade-offs with a staff engineer, all in the same week. You build your own tools. You use AI to prototype, analyze, and accelerate your work — building agents, writing scripts, creating automated workflows, whatever gets the job done fastest. Not because someone told you to, but because you can't imagine working any other way. What You Bring 8+ years in product management, with 3+ years at Staff/Principal level on platform, AI/ML, or infrastructure products Owned a multi-component platform serving multiple product teams, not just a single product Deep technical fluency: can read code, review architecture, and debug production issues alongside engineers Experience with AI/ML platforms: LLM orchestration, model evaluation, fine-tuning, RAG, agentic frameworks, or similar Experience governing platform contracts and managing how internal teams consume capabilities Built in enterprise SaaS environments with multi-tenant, compliance, and governance requirements AI-native workflow: You build with AI daily — creating agents, automating analyses, prototyping with code, building custom workflows. The specific tools don't matter (Cursor, Copilot, Claude, Replit, custom scripts — all count); what matters is that you've moved beyond prompting into building. Bonus Points Financial services or regulated industry experience Voice/ASR/TTS systems and real-time latency-sensitive products LLM evaluation frameworks, multi-agent orchestration, or RLHF/RLAIF Knowledge graph or RAG-based retrieval systems Built a platform team from scratch Our Values Act Like You're the Founder: Own the outcome from start to finish No Fear. Speak Your Mind: Candor moves us forward Pursuit of Excellence: Raise the bar, every time AI-First Mindset: Think automation, intelligence, and scale-first in every solution Don't Assume. Seek to Understand: Start with questions, not conclusions How We Work Every PM builds with AI daily. Our standard toolkit is Cursor, MCP integrations, and custom AI agents — and we onboard every new hire on these tools in their first week. We hold a high quality bar and move at startup speed. Flat organization. No empire-building. What We Offer 100% company-paid medical, dental, and vision coverage 401(k) with company match and financial wellness perks Discretionary PTO + paid parental leave Mental health, wellness, and family benefits Competitive equity with meaningful upside At Interface.ai, we are committed to providing an inclusive and welcoming environment for all employees and applicants. We celebrate diversity and believe it is critical to our success as a company. We do not discriminate on the basis of race, color, religion, national origin, age, sex, gender identity, gender expression, sexual orientation, marital status, veteran status, disability status, or any other legally protected status. All employment decisions at Interface.ai are based on business needs, job requirements, and individual qualifications. We strive to create a culture that values and respects each person's unique perspective and contributions. We encourage all qualified individuals to apply for employment opportunities with Interface.ai and are committed to ensuring that our hiring process is inclusive and accessible.