Director of Product, AI Experiences

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 systems
• Experience working as a UI/UX designer is a plus

What’s In It For You

• Build something new: Lead a newly formed team focused entirely on AI experiences
• Real ownership: Define how Pasito’s AI shows up for hundreds of thousands of users
• Direct impact: Your decisions will shape customer adoption, satisfaction, and revenue
• Strong partners: Work alongside experienced Product, Engineering, Design, and GTM leaders
• Growth: Join early and grow with the company as we scale product, team, and distribution
• Competitive compensation: Salary, meaningful equity, and full benefits: medical, dental, vision, 401(k) with match, life insurance, and flexible PTO
• Remote‑first: Work from anywhere in the U.S. with a highly collaborative team

Statement of Equal Opportunity

We are a company that values diversity and appreciates the benefits a diverse workforce produces for our team and clients. We welcome all qualified applicants to apply.