Pasito

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role As an AI/ML Engineer, you’ll work across backend systems, data pipelines, and AI/ML systems. You’ll help architect and build multi-agent systems, work across LLM development, agent orchestration, evaluation and deployment, owning the full development from prototype to production. As an early member of the engineering team, you’ll have real ownership and influence: shaping architecture, defining standards, and building systems that carriers, brokers, and employers rely on every day. What You’ll Do **Develop AI-native workflows **Architect and build scalable multi-agent systems with clear evaluation metrics, monitoring, fallback strategies, and cost controls for extracting and reasoning over complex benefits data. **Own backend and data-heavy systems **Design and own backend services, APIs, and data pipelines that power AI workflows, with a focus on correctness, scalability, observability, and long-term maintainability. **Collaborate cross-functionally **Work closely with Product, Design, Sales, and Client teams to understand customer workflows and translate them into durable technical solutions. **Continuously improve systems **Refine existing architecture, reduce operational complexity, and help define what “great” looks like as the platform scales. Who You Are A full stack engineer with 3+ years of experience building complex web applications  Comfortable owning backend systems and APIs, while collaborating closely on frontend experiences Experienced integrating AI / LLM-powered systems into real products Curious, adaptable, and energized by working in fast-moving, ambiguous environments A collaborative partner to product managers, designers, and other engineers Technical Experience We’re Excited About 3+ years of experience in software engineering Strong backend engineering experience with Node.js and Python. Hands-on experience integrating and operating AI systems using frameworks such as LangGraph, LangChain, LlamaIndex, and model SDKs (OpenAI, Anthropic, Google AI Studio), including prompt/version management and tool calling. Bonus: AWS, MySQL at scale, and JavaScript frameworks. Experienced building, deploying, and operating multi-step or multi-agent AI systems in production, with ownership of correctness, latency, cost, and failure handling Experienced designing and operating RAG or persistent memory systems using vector databases (e.g., Pinecone, Turbopuffer), including indexing strategies, retrieval evaluation, and performance/cost tradeoffs Experienced building production-grade evaluation and monitoring pipelines for AI systems (e.g., LangSmith, Langfuse, MLflow), including offline evals, live metrics, and regression detection Experience building document ingestio

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role Pasito is hiring a Data Analyst who understands that data is most powerful when it drives decisions. You'll partner closely with our Data Engineer to design and build dashboards that translate complex data into clear, actionable insights for internal teams, client stakeholders, and executive sponsors. You'll own Pasito's ROI narrative and product analytics story — identifying the metrics that best demonstrate our product's impact, ensuring they hold up to scrutiny, and communicating them with the confidence and precision that earns trust at every level of an organization. What You’ll Do Own the analytics narrative — identify, define, and continuously refine the metrics that best demonstrate Pasito's product value and ROI to external stakeholders. Lead product analytics — define how Pasito's product is described and understood through data, building the reporting framework that captures engagement, adoption, and outcomes in a way that is accurate, compelling, and tailored for each stakeholder. Design data dashboards in collaboration with our Data Engineer, translating business and product questions into intuitive, visually compelling reporting experiences. Partner cross-functionally with Product, Customer Success, Sales, and Leadership to understand what questions matter most and ensure the right data is surfaced at the right time. Prepare and deliver data presentations to internal senior leadership and external executive sponsors — communicating findings clearly, confidently, and without jargon. Enable others to present data effectively — coach and train internal team members on how to communicate data-driven insights with confidence, and prepare presentation-ready work that others can own and deliver when needed. Proactively explore data to uncover trends, anomalies, and opportunities that the business hasn't yet thought to ask about. Establish and maintain data definitions and reporting standards so that everyone is working from a single source of truth — including standardized language for how the product's performance is described internally and externally. Conduct competitive analysis — research the metrics and benchmarks that peer companies and competitors report on, evaluate their relevance to Pasito, and make informed recommendations about whether and how to adopt them into our reporting framework. Partner with Marketing to identify and maintain the top data points the sales team needs to effectively communicate Pasito's product value in the field — ensuring those numbers are current, accurate, and easy to use. Collaborate with the Partnerships team to surface data-driven insights that inform partner strategy — including identifying early risk indicators and establishi

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role We’re hiring a Director of Product, AI Experiences to lead the team responsible for how Pasito’s AI shows up in the hands of our users. This role owns the end-to-end product experience across Pasito’s stakeholders: brokers, carriers, employers, and employees. While our AI Foundations team builds the underlying AI agents and infrastructure, the AI Experiences team translates those capabilities into intuitive, usable, and high-impact product experiences. You’ll lead Product for AI Experiences, directly managing a designer and QA focused on experience quality, and partnering closely with the VP of Engineering for AI Experiences. You’ll also work hand-in-hand with our forward-deployed, client, and sales teams to ensure what we ship solves real customer problems. This role is for a hands-on product leader who moves fast, thrives in complexity, and brings deep empathy for customers. What You’ll Do Translate AI capabilities into usable products Partner closely with the AI Foundations team to turn AI agents and backend capabilities into intuitive, reliable, and scalable user experiences. Lead and develop the AI Experiences product team Directly manage Design and QA for AI Experiences team, setting clear priorities, high standards, and a strong execution rhythm. Work deeply with customers and the field Spend meaningful time with clients, forward-deployed teams, and sales to understand workflows, pain points, and success criteria, and reflect those insights in product decisions. Partner tightly with Engineering Collaborate daily with the VP of Engineering for Experiences and the entire Experience engineering team to align on scope, sequencing, tradeoffs, and delivery. Drive execution and accountability Run planning, prioritization, and delivery across multiple workstreams while keeping teams aligned and focused. Who You Are A product leader with deep empathy for users and customers Highly organized, structured, and comfortable juggling multiple priorities at once Comfortable operating at both strategic and execution levels Low-ego, collaborative, and motivated by building great products Energized by ambiguity and fast-moving environments Excited to build with AI and shape how AI is experienced by real users Technical Experience We’re Excited About 8+ years of experience in product management, including leadership of complex, user-facing products Experience building and scaling B2B or B2B2C SaaS products, ideally in regulated or complex domains Strong customer-facing experience, including working directly with enterprise clients Experience translating technical or AI-driven capabilities into intuitive product experiences Prior experience working with AI-powered products or agentic syst

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role We’re hiring a Product Owner to own and drive the development of key products at Pasito, including our employee engagement suite, insurance RFP workbench, and broker and carrier enrollment workbench.  This role sits at the center of the company, bridging customer needs and technical execution. You will report to the VP of Product & Data and take full ownership of the product and feature lifecycle for your areas, from idea to launch and beyond. This is a highly hands-on role for someone who is exceptionally organized, an excellent communicator, and excited to own execution end-to-end. What You’ll Do Own the full product lifecycle Take products and features from concept to launch and beyond  Define requirements, write clear product specs, and manage execution through delivery Ensure high quality and usability before anything ships Drive day-to-day product execution Work closely with engineering, design, data, quality assurance, and forward-deployed teams to prioritize, scope, and ship features Maintain clear roadmaps and ensure timelines are met Identify tradeoffs quickly and keep development moving forward Bridge customer needs and product decisions Work closely with internal teams and clients to understand workflows, pain points, and opportunities Translate real-world use cases into clear product requirements Understand what users ask for and what they actually need, ensuring what we build solves meaningful problems Own communication and rollout Partner with Marketing to clearly communicate product updates and launches Create high-quality written materials (release notes, product docs, internal updates) Ensure messaging is clear, polished, and aligned with product value Enable internal teams Train forward-deployed, sales, and client teams on new features and workflows Create documentation and materials that make products easy to understand and use Act as the internal expert for your product areas Who You Are An exceptional communicator with outstanding written and spoken English Highly organized and detail-oriented, and skilled at multi-tasking  Strong sense of ownership (you take responsibility for outcomes, not just tasks)  Comfortable operating in a fast-paced, ambiguous environment Low ego, highly collaborative, and focused on building great products Naturally curious about how systems work and how to improve them User-focused; you ground decisions in a genuine understanding of the people who will use our products Experience We’re Excited About 2–5 years of experience in product, engineering or a similar role Experience working cross-functionally with engineering, design, or technical teams Strong experience writing clear, structured documentation or product sp

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role We’re hiring a Strategic Partnerships Associate to support and scale Pasito’s carrier and broker partnerships. This is a highly execution-focused, client-facing role for someone who thrives at the intersection of partnerships, operations, and delivery. You’ll work closely with our partnerships, account management, and product teams to onboard partners, support go-to-market initiatives, and ensure successful execution across carrier and broker relationships. You’ll play a key role in helping partners adopt and expand their use of Pasito—owning operational workflows, supporting client deliverables, and ensuring a high-quality partner experience. This role is ideal for someone early in their career who wants exposure to partnerships, client strategy, and the U.S. benefits ecosystem, while building strong operational and commercial instincts. What You’ll Do Support partnership onboarding and execution Assist in onboarding new carrier and broker partners, ensuring smooth setup, configuration, and launch of Pasito across accounts. Drive partner enablement Help develop and maintain training materials, documentation, and enablement resources for partners. Support training sessions and ensure partners understand how to use and position Pasito effectively. Manage partnership workflows Coordinate day-to-day partner requests, track deliverables, and ensure timely execution across internal and external stakeholders. Build and deliver client materials Assist in configuring microsites, communications, and other partner-facing deliverables using templates and specifications. Ensure quality and accuracy QA partner deliverables, test workflows, and flag discrepancies before materials go live to ensure a high-quality experience. Support go-to-market initiatives Work with partnerships and marketing teams to support launches, campaigns, and co-branded initiatives with carriers and brokers. Collaborate cross-functionally Partner closely with Sales, Account Management, Product, and Engineering teams to resolve issues, improve workflows, and support partner success. Track and report on partner activity Maintain accurate records of partner activity, performance, and pipeline. Help identify opportunities for expansion and improvement. Who You Are Early in your career (1–3 years of experience) in partnerships, operations, client success, or similar roles Highly detail-oriented—you catch issues others miss and ensure work is accurate and polished Strong communicator with excellent written and spoken English Comfortable working in fast-paced, ambiguous environments Organized and process-driven, with the ability to manage multiple workflows simultaneously Curious and proactive—you ask thoughtful questions

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role We’re hiring a Strategic Partnerships Manager professional to join Pasito’s Forward Deployed team, focused on supporting and enabling our broker partners. This is an external-facing, consultative role for someone who enjoys working closely with clients, teaching complex AI tools in an approachable way, and ensuring partners get real value from the platform. You’ll own broker onboarding, training, and ongoing engagement, acting as a trusted partner throughout the relationship. You’ll work cross-functionally with Sales, Marketing, Product, Engineering and Operations to ensure brokers are confident, empowered, and successful using Pasito. What You’ll Do Broker Relationship Management Serve as the primary point of contact for broker questions, training needs, and engagement opportunities Build strong broker relationships through proactive communication and thoughtful problem solving Guide broker teams through onboarding after new business is signed, keeping all stakeholders aligned on next steps and timelines Coordinate between broker teams and internal Product, Design and Engineering teams to deliver Guides, Tables, Pages, and Microsites that meet branding and content requirements Conduct live training sessions to walk brokers through Pasito’s platform, use cases, and workflows Provide 1:1 consultations to ensure brokers can confidently onboard and support their employer clients independently Support Pasito’s growth into the Vendor-Broker-Client RFP process by building out standard workflows and outlining current industry pain points Product & Feedback Loop Act as the voice of the broker, sharing feedback and insights with Product and Engineering Identify opportunities to improve Pasito’s platform, training materials, and support resources Participate in product testing and QA to help ensure new features meet real-world broker needs Tracking & Reporting Track broker engagements, training sessions, 1:1 bookings, and qualitative feedback Report metrics and insights to the Consultant Engagement leadership team Use broker feedback and data to continuously refine onboarding, training, and engagement strategies Represent Pasito externally Participate in industry events, conferences, and webinars to build relationships and market presence. Who You Are Client-facing, personable, and comfortable leading conversations with external stakeholders Confident presenting, training, and teaching across different learning styles Highly organized and comfortable managing multiple brokers and workflows at once Collaborative and proactive; you enjoy working across teams to solve problems Comfortable receiving feedback and turning it into action Energized by helping others replatform with AI

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role We’re looking for a UI-heavy, product-focused Software Engineer to help us build the core product experiences that power Pasito’s AI workspace. We’re specifically looking for someone whose strength is building sophisticated, state-rich user interfaces, and who can operate across the stack as needed to deliver those experiences end-to-end. You’ll work closely with Product and Design, take deep ownership of complex UI systems, and help define how AI-native software should feel in a regulated, high-impact industry. As an early member of the engineering team, you’ll have real ownership and influence: shaping UI architecture, setting quality standards, and delivering mission-critical experiences for highly engaged clients. What You’ll Do Own complex, state-rich UI systems Design and build rich editing and collaboration experiences using ProseMirror / Tiptap and Yjs, with a focus on correctness, performance, and excellent UX. Build AI-native product experiences Integrate AI and LLM-powered workflows directly into the UI - especially within rich-text, data-dense, and collaborative environments. Collaborate cross-functionally Work closely with Product, Design, Sales, and Client teams to understand real customer workflows and translate them into durable product solutions. Continuously improve systems Refine existing patterns, challenge assumptions, and help define what “great” looks like as the product and team scale. Who You Are  A UI-first, product-driven engineer with 3+ years building complex web applications You care deeply about interaction quality, performance, and building interfaces that feel intuitive and trustworthy You have strong technical judgment and know when to prioritize innovation vs. stability You’re comfortable operating across the stack, with strength in frontend and user-facing systems You enjoy close collaboration with product managers and designers Technical Experience We’re Excited About Deep expertise building rich UI editors using ProseMirror / Tiptap Experience building real-time collaboration and local-first applications using Yjs Experienced with TypeScript, Node.js, and modern frameworks like Next.js Hands-on experience integrating AI / LLM-powered workflows (e.g., ChatGPT or Claude) into user-facing products Strong familiarity with frontend testing tools and best practices What’s In It For You Meaningful ownership: Build foundational systems used by carriers, brokers, employers, and employees at scale Real impact: Your work directly improves how people understand and use their benefits Growth: Join early and grow with the company as we scale product, team, and distribution Competitive compensation: Salary, meaningful equity, and full benefits: med