Building Clay’s Marketing Engine from Zero (with Matt Maiale, Clay’s First Marketing Hire)

Inside Braintrust: Scaling a Category-Defining AI Evals Platform (with Sarah Zeng)

Join me in conversation with Sarah Zeng, who has gone from investing to operating at the forefront of AI - first as one of the first 50 employees at Character AI and now scaling Braintrust. Braintrust is a go-to platform for AI evals and observability. They recently announced their $80M Series B, led by ICONIQ and joined by returnees a16z, Greylock, Elad Gil, basecase and others. Timestamps: 00:00 Introduction to Sarah Zeng and Her Journey 02:37 Transitioning from Investing to Startups 04:57 Joining Character AI 06:48 The Move to Braintrust 08:39 Effective Strategies for Chief of Staff Onboarding 10:03 Understanding Braintrust's Core Products 12:38 Navigating the Role of Chief of Staff 15:06 Growth in Consumer AI vs. Infrastructure AI 16:40 Braintrust's Rapid Growth and Market Position 19:20 Future of AI Evaluation and Observability 21:56 Rapid Fire

Designing the Standard for AI Detection (with Olivia, GPTZero's First Product Designer)

Join me in conversation with my friend Olivia Kusio, the first and founding product designer at GPTZero — one of the breakout AI companies of the last two years. Olivia joined as the 5th employee. Two years later, GPTZero has grown to millions of users and $25M+ in revenue. We cover: 🎨 Designing for trust in AI products 🧠 How students and teachers are really using AI 💬 Building culture inside a rocketship startup & more Timestamps 00:00 Introduction to GPTZero and Olivia's Journey 01:51 The Role of a Product Designer at GPTZero 03:42 Building a Team and Initial Projects 05:22 Designing for Speed and Quality 06:49 The Evolution of Design Tools 08:26 Design Principles for Trust and Credibility 09:06 User Interaction with AI in Education 12:36 The Responsible Use of AI in Education 15:28 Scaling Company Culture at GPTZero 19:06 Moments of Realization and Responsibility 20:58 Lightning Round: Insights and Inspirations

Inside the First BizOps Seat at Column (with Charlie Liao)

What does it look like to be the first BizOps hire at a company rebuilding banking from the ground up? In this episode, I chat with Charlie Liao, who joined Column - founded by William Hockey, one of Plaid's co-founders - when the team was around 70 people. We talk about what drew him from fintech investing to operating, how he’s defining the BizOps function at one of the most technical startups in fintech, and his advice for founders hiring their first BizOps person. Enjoy! Timestamps 00:00 Introduction to Column and Charlie 01:05 Transition from Investing to Operations 02:53 Joining Column: The Decision Process 05:50 Navigating Startup Risks and Responsibilities 08:39 Defining Success in BizOps 10:41 Handling Ambiguous Projects 12:00 BizOps and Cross-Functional Collaboration 12:41 Importance of Documentation and Processes 14:00 Balancing Speed and Structure 14:42 Setting Boundaries in a Utility Role 15:49 Scaling the BizOps Team 16:54 When to Hire Your First BizOps Person 18:06 Qualities of a Great First Hire 19:46 Mindset for Quick Decision Making 20:23 Rapid Fire Questions and Closing Thoughts

Building Clay’s Marketing Engine from Zero (with Matt Maiale, Clay’s First Marketing Hire)

When Matt Maiale joined Clay, the go-to-market platform helping sales teams find, enrich, and personalize outreach at scale, there were just five people and no marketing playbook. Clay now serves thousands of customers and recently raised a $100M Series C at a $3.1B valuation. In this conversation, we talk about how Matt chose Clay at the seed stage, built the company’s growth flywheel, and developed a bottoms-up marketing approach that scaled organically. 00:01 — Intro 00:55 — Matt’s path before Clay 01:56 — Finding & evaluating Clay 02:53 — How Clay closed him 04:06 — Week 1 as first marketer 05:04 — Building the growth flywheel 05:28 — Fixing conversion 06:14 — ICP & vertical focus 07:47 — Simple wins (Buy button, funnel fixes) 07:47 — Waitlist as a lever 10:08 — Messaging: startups vs. enterprise 11:40 — Defining the role 12:29 — “Bottoms-up marketing” 14:11 — Referrals & community 15:57 — Spend philosophy 17:07 — Compounding growth channels 18:30 — Product education 20:07 — Emojis to describe Clay 21:45 — Culture bits 23:16 — Misconception: growth at all costs 24:18 — Hiring your first marketer 25:06 — Post-Clay travel 25:59 — What he’s building now ---------------------------------------- To learn more about Matt and what he’s working on: https://instantdomainsearch.com/ [https://instantdomainsearch.com/] https://mattmaiale.substack.com/ [https://mattmaiale.substack.com/] https://x.com/maiale [https://x.com/maiale]

Lessons & Early Days Inside Climate Unicorn Watershed (with Tammy Tseng)

In this conversation, I get to talk with Tammy, climate unicorn Watershed's 25th employee and second data hire. We discuss Tammy's journey from Quora to Watershed, how founders can attract and retain early talent, the evolution of data roles in startups, and more. Enjoy! Timestamps: 00:00 Introduction to Tammy and Watershed 01:21 Choosing Watershed 03:28 Recruitment Insights: What Watershed Did Right 04:11 Transitioning from Quora to Watershed 05:20 First Days at Watershed: The 'First Day Ship' Tradition 06:34 Advice for Early Function Roles 08:01 Early Decisions and Their Long-Term Impact 09:15 Recognizing the Need for More Data Talent 10:17 Growing with Watershed: Retaining Early Talent 11:46 Navigating Career Transitions 13:35 Unlearning as the Company Scales 14:47 Key Moments in Watershed's Journey 15:55 The Role of Culture in Team Dynamics 16:18 Navigating Climate Challenges as a Company 17:50 Hiring for Data Roles: Insights for Founders 19:20 Evolution of Data Science Roles in the Industry 21:10 Advice for New Employees in Startups 23:06 Lightning Round 25:29 996 Startup Work Culture ---------------------------------------- More on Watershed: https://watershed.com/ [https://watershed.com/] More on Tammy: https://www.linkedin.com/in/tammytseng/ [https://www.linkedin.com/in/tammytseng/] More on Sarah: https://www.linkedin.com/in/sarah-du/ [https://www.linkedin.com/in/sarah-du/]