The Product Podcast

HP is best known for hardware and printers. Faisal Masud is turning it into a software and AI company, and he thinks the era of stacked management layers is ending. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Faisal Masud, SVP and President of Worldwide Digital Services at HP, for a candid conversation about building enterprise AI, and what it does to how companies are actually run.

Faisal has a rare vantage point: two decades across Amazon, eBay, Groupon, and Alphabet's Wing (the drone delivery moonshot, where he was COO), then CEO of the $1.5B commerce platform fabric, and now running all of HP's commercial software business. He explains why a hardware giant deliberately built a standalone software unit, how the thesis (collect telemetry from HP's devices, turn it into insights that serve customers) became the Workforce Experience Platform, and why HP stopped reselling third-party software to sell its own owned-IP products instead.

The heart of the conversation is what AI is doing to organizations. Faisal argues that AI is demonstrably making extra layers of management unnecessary, because the monitoring, data collection, and aggregation those layers existed to do can now be handled by individuals and agents. His provocative framing: the future "manager" is managing agents, not people, and managers will have to know far more than just how to manage. He's equally blunt about the hype, AI is part of your strategy, not your strategy, adoption metrics alone prove nothing, and "everything is easier with AI until you go to production, which is a whole different ball game," where token budgets and real ROI bite. He also gives a working leader's read on the competitive landscape (OpenAI on the frontier, Amazon's moat, Microsoft Copilot's gains) and how his own PMs and developers use Claude, Codex, and Cloud Code every day.

What you'll learn:
Why AI is making additional layers of management unnecessary, and what replaces them
The shift from managing people to managing agents, and why managers will need to know more
Why a hardware company like HP built a standalone software and AI business
How device- and OS-agnostic telemetry became the Workforce Experience Platform
Why HP stopped reselling third-party software to sell owned-IP products
Why "AI is part of your strategy, not your strategy," and why adoption metrics aren't enough
The real wall: AI makes building easy until you hit production, budgets, and token limits
How Faisal pushes PMs on what should be done with AI vs. what needs a human in the loop
A working read on OpenAI, Amazon, and Microsoft Copilot in the enterprise
What Faisal predicts for headcount and org structure in the mid-term

Connect with Faisal Masud: President, HP
LinkedIn: https://www.linkedin.com/in/faisal/

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

About HP Digital Services: HP's Digital Services division builds the commercial software HP sells into enterprises and channel partners, including the Workforce Experience Platform, which uses AI to anticipate and resolve employees' IT needs across a device- and OS-agnostic fleet.

About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech.
Social Links:
Find out more about Product School here
Follow our Podcast on TikTok here
Follow Product School on LinkedIn here

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.
Social Links:
Find out more about Product School here
Follow our Podcast on TikTok here
Follow Product School on LinkedIn here

Most apps optimize for time on screen. Hinge optimizes for you leaving. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Ben Celebicic, Chief Product and Technology Officer at Hinge, the dating app "designed to be deleted," to unpack how you build a product whose North Star is great dates, not engagement, and still chase a billion dollars in revenue.

Ben has been at Hinge for 11 years, since the 2015 relaunch, and recently became one of a growing number of leaders to hold both the product and technology mandate in a single CPTO role. He and Carlos get into the healthy tension between the CPO instinct (ship fast, innovate) and the CTO instinct (protect quality and infrastructure), and how he now runs that debate inside one person and across a team of nearly 300. He lays out Hinge's monetization philosophy in two principles: build the free experience so everyone can succeed, and only charge for things you can't give away free without breaking the ecosystem (which is why fewer than 15% of users pay). He explains how a dedicated culture and consumer insights team studies real daters to find core needs, how generative AI now enables per-user profile coaching that was impossible before, why trust and safety makes up roughly a third of the entire Hinge organization, and where he draws the line on AI-assisted engineering today. He closes on Hinge's mission to reach $1 billion in revenue in 2027.

What you'll learn:
- Why "designed to be deleted" is a real product principle, and how an anti-engagement North Star works
- How to run the CPO-vs-CTO tension, even when both roles live in one person
- Hinge's two-principle monetization model, and why fewer than 15% of users pay by design
- Why you should only charge for things that would break the ecosystem if they were free
- How a culture and consumer insights team turns real dater problems into features
- How generative AI enables personalized profile coaching that wasn't possible before
- Why trust and safety is about a third of the whole org, and how AI powers it
- Where an engineering-background leader draws the line on AI-built product today
- The mission to hit $1B in revenue in 2027, and the "obsess over user needs" formula behind it

Connect with Ben Celebicic: CPTO, Hinge
LinkedIn: https://www.linkedin.com/company/lrb-podcasts/about/

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

About Hinge: Hinge is the dating app "designed to be deleted," built to help people get off the app and out on great dates. Founded by Justin McLeod and relaunched in 2015, Hinge is part of Match Group's portfolio of dating and social discovery apps.

About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech.
Social Links:
Find out more about Product School here
Follow our Podcast on TikTok here
Follow Product School on LinkedIn here

One month before Bolt exploded, Eric Simons was preparing to wind the company down. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Eric Simons, CEO of Bolt, to tell the story behind one of the fastest revenue ramps software has ever seen, and what he learned building toward it for seven years first.

Eric is a high-school dropout who approaches life from first principles and treats endurance sports as training for the pain of building a company. He and Carlos trace the near-death moment (a board meeting set to start spinning the company down was one month away), the bet on WebContainers (an operating system Eric's team wrote to run in WebAssembly inside the browser, so you can build real full-stack apps from a browser tab, the way Figma brought design to the web), and the ramp that followed: zero to about $5M ARR in the first 30 days, then to roughly $20M ARR within two months, a curve that normally takes companies years. He explains why StackBlitz is now going deep on professional builders (PMs, designers, engineers), how Bolt is solving the hard part of turning AI-generated prototypes into production code your engineering team will actually sign off on, and why he frames the market like the ChatGPT-vs-Anthropic split: pick a specific ICP and workflow instead of spraying money at everything. He closes on the open-weights bet (StackBlitz was the earliest backer of Vite), aggressive usage-based pricing, and why cheaper open models are closing the last bit of distance to the labs.

What you'll learn:
- The near-death story: one month from shutting down, then a record revenue ramp
- Why the WebContainer bet (a real OS running in the browser) took seven years and made Bolt possible
- What a 0-to-$20M-ARR-in-two-months curve actually looks like, and why it's so rare
- Why StackBlitz is focusing on professional product builders, not just cute prototypes
- How to turn an AI prototype into production code your engineering team signs off on
- The "ChatGPT vs. Anthropic" framing: why going deep on one ICP beats spraying money everywhere
- Why first-principles thinking and endurance sport shape how Eric builds
- The open-weights bet, aggressive usage-based pricing, and open models catching up to the labs

Connect with Eric Simons, CEO, Bolt
LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/

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

About Bolt / StackBlitz: StackBlitz is the company behind Bolt (bolt.new), an AI-powered web development platform that lets anyone build real full-stack applications from a browser tab, powered by its in-browser WebContainer operating system. StackBlitz was also the earliest backer of the open-source Vite project.

About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech.
Social Links:
Find out more about Product School here
Follow our Podcast on TikTok here
Follow Product School on LinkedIn here

What do you do after you've founded a company, sold it to Databricks, and could coast? Amandeep Khurana went back to being hands-on. In this episode of The Product Podcast, Carlos Gonzalez de Villaumbrosia (CEO at Product School) talks with Amandeep Khurana, now on Anthropic's go-to-market team, about a career built on deliberately choosing the harder path.

Amandeep traces the whole arc: training as an engineer, moving to the Valley to go customer-facing at Cloudera, catching the company-building bug "by osmosis," and founding Okera in 2016, which eventually exited to Databricks. He talks about what he learned in the ups and downs of running a startup, why he later joined AWS as a founding PM (on Kiro) to run four zero-to-one initiatives instead of taking a comfortable management track, and how he thinks about the two fundamental jobs in any company: building a product and selling a product. He and Carlos dig into the tension between being a hands-on builder and being a manager, how to decide which domains are worth jumping into when you know nothing, and why he joined Anthropic to work on bringing AI safely to enterprises. It's a candid conversation about career design, first-principles decision-making, and staying close to the work.

What you'll learn:
- Why Amandeep repeatedly chooses the "harder path," and how first-principles thinking drives his career decisions
- What founding and exiting Okera (to Databricks) actually taught him about company building
- Why he went back to hands-on building instead of a pure management track
- How to think about the two core jobs in any company: building the product and selling it
- How to decide whether to jump into a domain you know nothing about
- What running four zero-to-one initiatives inside a big company teaches you
- Why he moved into GTM and enterprise AI adoption at Anthropic
- How to stay hands-on as your career pulls you toward management

Connect with Amandeep Khurana:
Anthropic (GTM / Enterprise); previously co-founder and CEO of Okera, founding PM for Kiro at AWS
LinkedIn: https://www.linkedin.com/in/amansk/

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

About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech.
Social Links:
Find out more about Product School here
Follow our Podcast on TikTok here
Follow Product School on LinkedIn here