Toast was built long before generative AI existed. So how do you weave AI agents into a platform that thousands of restaurants already run their business on, without breaking the thing that works? In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Maggie Crowley, VP of Product at Toast, to unpack what it actually takes to build AI into mature, pre-AI SaaS.

Maggie is a former Olympic speed skater (fifth at the 2006 Winter Olympics) turned product leader, with an MBA from Harvard and product roles across Drift, TripAdvisor, and Charlie Health before Toast. She was also a Product School contributor years ago, back in her Drift days, which is what makes this a fitting return. At Toast she leads product on Toast IQ, the company's AI layer for restaurant and retail operators. In this conversation, she and Carlos get into the genuinely hard parts: why the quality bar for building on an established platform is punishingly high, how her team actually shipped their first assistant (sitting in WhatsApp groups with real customers and turning it on for a few of them), and why you have to physically bring the AI to the user instead of assuming they'll discover it.

Maggie is refreshingly blunt that restaurant operators have zero tolerance for "AI for AI's sake." They don't care whether it's Anthropic, OpenAI, or an open-weight model under the hood; they only care whether you helped them run their business. She explains how the tight P&L of a restaurant forces real discipline about what's worth charging for, how Toast IQ Grow (an agent that drives demand and fills seats) became a breakthrough use case by slashing the cost of marketing work, and why she still manages a frontline team directly to stay close to how AI is changing the way products get built. The episode closes with a live demo of Toast IQ.

What you'll learn:
- How to build AI agents into a platform designed years before AI, without lowering the quality bar
- The scrappy build process: WhatsApp groups with customers and turning an assistant on for a few
- Why you have to bring the AI to the user, and why AI onboarding is an unsolved problem
- Why context (where the user is, what time, what role) is everything for an AI product
- Why restaurant operators have zero tolerance for "AI for AI's sake"
- How the tight P&L of a restaurant enforces discipline about what's worth building and charging for
- How Toast IQ Grow uses AI to cut the cost of marketing and drive real demand
- Why abstracting model choice (Anthropic vs. OpenAI vs. open weights) away from the user matters
- Why a product leader should keep a hand in how teams build, and manage close to the work
- A live look at Toast IQ answering real operator questions in plain language

Connect with Maggie Crowley:
VP of Product, Toast
LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/

Host: Carlos, CEO at Product School
LinkedIn: https://www.linkedin.com/in/villaumbrosia/

About Toast: Toast is an all-in-one platform built for restaurants and retail, spanning point of sale, payments, operations, and marketing, now including Toast IQ, its AI layer for operators.

About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech.

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