The Room Podcast

In this episode of The Room Podcast, Madison and Claudia sit down in the studio with Cecilia Ziniti, co-founder and CEO of GC AI. Cecilia shares how growing up as an immigrant, working inside Yahoo’s early trust and safety team, and serving as counsel at technology companies shaped her path from law to entrepreneurship. Cecilia explains the moment a pre-ChatGPT language model convinced her that legal work could change, and how she and co-founder Bardia set out to build a tool for in-house legal teams. She talks about finding early customers, following unexpected signals from the market, fundraising, and why legal buyers quickly saw value in a product built around their actual work.
The conversation turns to agents: how a legal team can delegate multistep work, why lawyers need a clear record of what an agent checked, and what AI may free them to do creatively and strategically. Cecilia also looks ahead to how legal teams could work in 2029, the questions of trust and responsibility that come with more capable agents, and the teachers in her family who shaped her approach to helping people adopt new technology.
Learn more about Cecilia Ziniti and explore GC AI.
(04:15) Where did Cecilia grow up, and how did it shape her worldview?
(05:14) Did Cecilia always think she would become a founder?
(06:34) Working at Yahoo before law school
(07:50) What trust and safety meant in the early days of consumer technology
(10:14) Helping the law keep pace with new technology at Cruise
(11:46) What Amazon Alexa and autonomous vehicles taught Cecilia about AI
(13:58) The pre-ChatGPT moment that led to GC AI
(15:57) Meeting co-founder Bardia and deciding to build together
(19:37) Finding early customers and following signals from the market
(20:46) GC AI’s first investors and fundraising lessons
(23:34) Building a legal AI product around what in-house teams need
(26:50) What an investor called violent product-market fit
(27:10) Staying focused when a new model launch shakes the market
(28:53) How GC AI fits into everyday business and legal workflows
(33:48) What becomes possible when lawyers can delegate more of the work
(38:13) AI, legal strategy, and creative thinking
(39:53) From AI interfaces to agents that complete multistep legal tasks
(42:57) Why legal agents need trust, accountability, and a record of their work
(44:14) Who takes responsibility when an agent acts on your behalf?
(47:52) What could a legal team look like in 2029?
(49:12) The remaining gaps in trust, data protection, and judgment
(50:18) Curiosity and becoming an AI boss
(52:40) What’s next for GC AI?
(53:21) What’s next for Cecilia and the team?
(53:54) A woman who has had a profound impact on Cecilia’s life and career
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Brought to you by: Rippling, Gradial, and Perkins Coie
WX Productions

In this episode of The Room Podcast, we speak with Sergi Bastardas, co-founder and CEO of Orbio AI, a platform using autonomous agents to coordinate the employee journey for frontline workforces. Sergi traces his path from a small town near Barcelona to joining Amazon Spain in its earliest days, and building a global supply-chain business. He shares how a family history of entrepreneurship, a curiosity about the wider world, and Amazon’s culture of operational excellence shaped the way he builds companies.
He explains why HR is fundamentally a system of conversations and unstructured data and why Orbio was designed as an agent-native product rather than an AI add-on. From screening and scheduling to onboarding, retention, and exit interviews, Orbio’s agents work across voice, WhatsApp, text, and Teams while keeping people in control of employment decisions.
In this conversation, Sergi breaks down the company’s expansion across languages and markets, what incumbent HR platforms would need to rebuild to become truly agent-native, and why he believes AI will empower frontline workers rather than simply replace them. He also reflects on fundraising, building a global company from Europe, balancing marriage with constant travel, and the coach who changed how he experiences the founder journey.
Learn more about Sergi Bastardas on LinkedIn and explore Orbio AI.
(03:52) Where Sergi grew up and how it shaped his worldview
(06:48) Did Sergi always think he would become a founder?
(08:13) Joining Amazon Spain in its earliest days
(11:18) From Amazon and supply chains to the frontline workforce problem
(13:04) Choosing experienced co-founders for Orbio
(15:52) What AI-native HR means—and why agents are not a bolt-on
(19:03) A day in the life of an Orbio agent
(26:53) Launching first in Spanish and adapting voice agents across markets
(28:07) Orbio’s Series A and the first investors who said yes
(30:07) Building a global company from Europe
(33:02) AI adoption across different countries and cultures
(35:47) Voice infrastructure, LiveKit alternatives, and local-language models
(37:29) Why incumbent HR platforms cannot easily replicate Orbio
(40:07) The future of work with people, agents, and robotics
(42:36) What’s next for Sergi personally
(43:28) A woman who profoundly shaped Sergi’s life and career
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Brought to you by: Rippling, Gradial, Ashurst Perkins Coie
WX Productions

In this episode of The Room Podcast, we speak with Caitlin Leksana, co-founder and CEO of Fazeshift, a company building AI agents for accounts receivable. Caitlin traces her path from growing up outside Washington, D.C., and studying mechanical engineering at Georgia Tech to water-desalination research, BCG, Harvard Business School, and entrepreneurship. She shares how a classmate became her co-founder, why their first crypto startup failed to find product-market fit, and how they found the conviction to pivot instead of walking away.
Caitlin explains how her own messy invoicing spreadsheet led the team to hundreds of customer-discovery conversations and eventually to Fazeshift. She breaks down what changed when the founders started with a customer problem instead of a product idea, how Y Combinator helped them find momentum, and what she learned about fundraising, hiring, and building with a co-founder.
The conversation also explores vertical AI in finance: why reliable automation starts with connecting messy data across ERPs, banks, inboxes, and industry-specific systems; how Fazeshift combines AI agents, browser workflows, and hands-on deployments; and why enterprise buyers want solutions to concrete problems rather than abstract AI capabilities.
Learn more about Caitlin Leksana on LinkedIn and explore Fazeshift.
(04:12) Where did Caitlin grow up, and how did it shape her worldview?
(05:14) Did Caitlin always think she would become a founder?
(07:01) Meeting her co-founder at Harvard Business School
(09:00) Starting their first company and realizing it was time to pivot
(11:17) How founders know when to stop pushing and change direction
(12:40) Customer discovery and finding the accounts receivable problem
(16:19) Building the MVP and joining Y Combinator
(18:52) Finding Fazeshift’s first investors and navigating fundraising
(21:50) Hiring mistakes and lessons from building after the pivot
(24:10) How the Y Combinator community supported Fazeshift
(29:43) Is Fazeshift a vertical AI company?
(30:36) Selling the solution versus selling the AI
(31:52) Why accounts receivable needed AI instead of traditional software
(34:39) Who buys Fazeshift, and who uses it day to day?
(36:54) Fazeshift’s product modules, pricing, and customer experience
(39:16) Connecting data across ERPs, banks, inboxes, and customer systems
(41:27) How Fazeshift deploys agents into messy enterprise workflows
(43:50) Letting customer problems shape the product roadmap
(45:07) Rebuilding browser agents as the technology improves
(46:08) Partnerships with accounting firms, private equity, and industry software
(48:38) How Caitlin’s role is changing as Fazeshift grows
(49:47) A woman who has had a profound impact on Caitlin’s life and career
For The Room Podcast in your inbox every week, subscribe to our newsletter.
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Brought to you by: Rippling, Gradial, and Perkins Coie
WX Productions

In this episode of The Room Podcast, we speak with Doug Tallmadge, co-founder and CEO of Gradial, a company building AI agents to help enterprise marketing teams execute work across their tools and campaigns. Doug traces his path from growing up in Cincinnati and studying physics at Dartmouth to joining SpaceX and helping build Starlink. He shares what working through seemingly impossible engineering challenges taught him and why finding a market for a startup can be a very different problem from building a product people already want.
After ChatGPT launched, Doug and his longtime friends left their jobs to start a company. He explains how their broad ambition to bring AI into enterprise work became a focused business in marketing, where campaign briefs, creative assets, tickets, and manual handoffs create a significant operational burden. In this conversation, Doug breaks down how Gradial’s agents have evolved alongside the models, what it takes to earn enterprise trust, and why marketers should be able to plan their budgets without worrying about tokens. He also reflects on fundraising setbacks, managing the emotional swings of building a company, and the professor who backed an unconventional student project that helped launch his career.
Learn more about Doug Tallmadge on LinkedIn and explore Gradial.
(04:13) Where did Doug grow up, and how did it shape his worldview?
(04:50) Did Doug always think he would become a founder?
(05:40) Studying physics at Dartmouth and choosing SpaceX over finance
(08:31) Building Starlink through existential engineering and business challenges
(11:39) Discovering product-market fit versus engineering a product people already want
(13:18) The moment Doug decided to start Gradial
(14:39) Why enterprise work runs on tickets—and why Gradial focused on marketing
(16:49) What goes into a marketing campaign, from brief to distribution
(20:22) Starting a company with longtime friends and roommates
(22:53) Narrowing the product after the first weeks of disillusionment
(24:18) Gradial’s first investor and lessons from early fundraising
(29:41) Managing the emotional swings of the founder journey
(31:53) When the original plan failed and it was time to focus on marketing
(34:19) How Gradial’s agent architecture evolved alongside the models
(38:02) Better models and the future of long-duration marketing work
(41:23) Enterprise security, procurement, and integration with existing systems
(42:37) Helping marketers spend more time on creative work
(43:36) Pricing AI agents and making marketing budgets predictable
(48:15) What’s next for Gradial
(49:36) What’s next for Doug outside the company
(49:58) A woman who has had a profound impact on Doug’s life and career
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Brought to you by: Rippling, Gradial, Ashurst Perkins Coie
WX Productions

In this episode of The Room Podcast, we sit down with Ann Crady Weiss, co-founder and CEO of Hatch, to trace the path from her Silicon Valley upbringing and early career in law and technology to building one of the most recognizable names in sleep. Ann shares how her family’s connection to Intel shaped her entrepreneurial ambition, what she learned at Wilson Sonsini and Yahoo, and how the acquisition of her first startup prepared her to build again.
Hatch began with a personal problem and evolved from a baby-focused hardware company into a broader sleep platform for children and adults. Ann explains how customer behavior led the team into the adult market, why emotional design and organic love became central to the brand, and how Hatch balances slower hardware cycles with a software-led organization and a growing library of bedtime content.
The conversation also covers Hatch’s appearance on Shark Tank, the long relationship with True Ventures, an early move into Costco, and the discipline of building with real unit economics. Ann shares what she has learned as both a founder and venture partner, why timing and luck matter more than entrepreneurs often admit, and why Hatch emphasizes better sleep habits, phone-free routines, and contactless tracking rather than scores or constant monitoring—even as AI changes how products are built.
Learn more about Ann Crady Weiss on LinkedIn and check out Hatch on their website.
(04:13) Ann’s Silicon Valley childhood and family connection to Intel
(05:05) How Ann’s uncle joined the early Intel team
(05:35) Did Ann always think she would become a founder?
(06:54) How law, Wilson Sonsini, and Yahoo shaped Ann’s early career
(08:59) The acquisition of Ann’s first startup and the path to Hatch
(10:45) The personal need and original product behind Hatch
(12:47) Why Hatch expanded from baby products into the adult sleep market
(14:53) How founders can pursue a large opportunity without losing focus
(16:22) Building emotional connection through product and brand design
(18:14) What founders should understand about hardware iteration
(19:30) The Hatch Sleep Clock and a different approach to sleep tracking
(22:47) Pitching on Shark Tank and partnering with Chris Sacca
(26:03) True Ventures and the first investors to believe in Hatch
(29:27) Setbacks, Costco, and lessons from expanding too early
(32:09) Building a sustainable business with real unit economics
(34:05) Hatch+ content and the case for phone-free sleep
(37:37) Building customer trust and protecting bedroom privacy
(39:29) How Hatch differs from wearables and other sleep trackers
(41:05) What Ann has learned as a founder and venture partner
(44:24) The future of sleep technology in the age of AI
(46:47) Building products that make people feel calmer, not monitored
(48:17) What’s next for Hatch
(49:33) A woman who profoundly shaped Ann’s life and career
For The Room Podcast in your inbox every week, subscribe to our newsletter.
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Check out our guide to podcasting here!
Don't forget to subscribe to our channel on YouTube, Spotify, and Apple Music!
Brought to you by: Rippling, Gradial, Ashurst Perkins Coie
WX Productions