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

Join me in conversation with Julia Govberg, Chief of Staff at Clay.Julia joined Clay at ~90 people around their Series B. Almost two years later, the team is close to 600, and just raised a Series D from Wellington, Sequoia, Meritech, and First Round.Timestamps00:00 Introduction to Julia and Clay01:53 Journey from First Round Capital to Clay04:30 Understanding the Chief of Staff Role06:32 Quarterly Planning and Cross-Functional Collaboration08:57 Scaling Challenges10:45 Talent Acquisition Strategies10:52 Leadership Dynamics and CEO Insights11:03 Time Management and Prioritization14:29 Transitioning from PLG to Enterprise Sales15:55 Leveraging LinkedIn for Brand Growth17:31 Building a Passionate User Community19:57 Learning and Adapting in a Chief of Staff Role25:15 Embracing Negative Maintenance as an Operating Principle28:55 Quickfire Insights and Advice

Join me in conversation with Kaitlyn Henry, Chief of Staff at Motherduck. Prior to Motherduck, Kaitlyn was CoS at dbt Labs, where she helped the company grow past $100M ARR, build out its exec team, and execute its merger with Fivetran.Timestamps:00:00 Introduction to Kaitlyn Henry and Motherduck02:39 Career Path: From Venture to Chief of Staff04:48 The Role of Chief of Staff: Expectations vs. Reality07:19 Prioritizing Projects as Chief of Staff12:00 Measuring Success in the Chief of Staff Role14:28 Scaling Companies: Lessons from dbt17:00 Investing Insights: Operator vs. Investor Perspectives19:31 Hiring Leaders: Building Effective Executive Teams21:38 Post-dbt Fivetran merger28:00 Transitioning to Mother Duck29:49 Choosing the Chief of Staff Role31:24 Lessons Learned from DBT34:33 Building Trust with Executives37:21 Navigating the AI Era at Mother Duck

Join me in conversation with Alex Zhang, Nooks' first PM and now Group PM. Nooks is an AI platform building the agent workspace for GTM teams, backed by Kleiner Perkins and Lachy Groom. Alex joined as employee ~50 and is now a group PM, driving many of Nooks 0 to 1 product bets.Timestamps:00:00 Introduction to Alex Zhang and Nooks02:15 Career Journey: From DoorDash to Nooks03:43 Understanding Nooks: The AI Sales Platform06:30 Human vs. AI in Sales:09:04 Transitioning from SaaS to AI Native Products10:52 Creative Solutions: Using AI for Sales Training12:33 Debugging AI Features: Identifying the Issues13:14 Exploring AI Interaction and Latency Challenges14:54 Expanding Product Surface Area16:54 Growth and Evolution: Alex's Journey at Nooks18:40 Lessons from "Failed" Products22:08 Rapid Fire

Join me in conversation with Grace Hua, head of Biz Ops at Cogent Security. Cogent is building autonomous cyberdefense and recently announced its $42M Series A led by Greylock and BCV.Grace joined as employee ~15 and has spent the last 9 months working across hiring, partnerships, fundraising, and more - essentially operating as an extension of the founders as the company scales.Timestamps:00:00 Grace Hua's Journey: From McKinsey to Cogent02:43 The Importance of People in Career Decisions05:11 Navigating the Startup Landscape: Finding the Right Fit07:06 Understanding the Cybersecurity Landscape09:34 Building a Company from the Ground Up11:43 The Role of Culture in Startup Success13:59 Establishing Trust and Relationships in a New Role16:31 Reflections on Time Management and Decision Making17:46 A Week in the Life of a BizOps Leader at Cogent21:28 Capitalizing on Opportunities with BizOps22:47 Effective Interviewing Techniques24:42 Closing Candidates in a Competitive Market27:01 Key Qualities for Founding BizOps Roles30:51 Leveraging AI for Enhanced Workflows33:31 Rapid Fire

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 Journey02:37 Transitioning from Investing to Startups04:57 Joining Character AI06:48 The Move to Braintrust08:39 Effective Strategies for Chief of Staff Onboarding 10:03 Understanding Braintrust's Core Products12:38 Navigating the Role of Chief of Staff15:06 Growth in Consumer AI vs. Infrastructure AI16:40 Braintrust's Rapid Growth and Market Position19:20 Future of AI Evaluation and Observability21:56 Rapid Fire

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& moreTimestamps00:00 Introduction to GPTZero and Olivia's Journey01:51 The Role of a Product Designer at GPTZero03:42 Building a Team and Initial Projects05:22 Designing for Speed and Quality06:49 The Evolution of Design Tools08:26 Design Principles for Trust and Credibility09:06 User Interaction with AI in Education12:36 The Responsible Use of AI in Education15:28 Scaling Company Culture at GPTZero19:06 Moments of Realization and Responsibility20:58 Lightning Round: Insights and Inspirations

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!Timestamps00:00 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

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 — Intro00:55 — Matt’s path before Clay01:56 — Finding & evaluating Clay02:53 — How Clay closed him04:06 — Week 1 as first marketer05:04 — Building the growth flywheel05:28 — Fixing conversion06:14 — ICP & vertical focus07:47 — Simple wins (Buy button, funnel fixes)07:47 — Waitlist as a lever10:08 — Messaging: startups vs. enterprise11:40 — Defining the role12:29 — “Bottoms-up marketing”14:11 — Referrals & community15:57 — Spend philosophy17:07 — Compounding growth channels18:30 — Product education20:07 — Emojis to describe Clay21:45 — Culture bits23:16 — Misconception: growth at all costs24:18 — Hiring your first marketer25:06 — Post-Clay travel25:59 — What he’s building nowTo learn more about Matt and what he’s working on:https://instantdomainsearch.com/https://mattmaiale.substack.com/https://x.com/maiale

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 Watershed01:21 Choosing Watershed03:28 Recruitment Insights: What Watershed Did Right04:11 Transitioning from Quora to Watershed05:20 First Days at Watershed: The 'First Day Ship' Tradition06:34 Advice for Early Function Roles08:01 Early Decisions and Their Long-Term Impact09:15 Recognizing the Need for More Data Talent10:17 Growing with Watershed: Retaining Early Talent11:46 Navigating Career Transitions13:35 Unlearning as the Company Scales14:47 Key Moments in Watershed's Journey15:55 The Role of Culture in Team Dynamics16:18 Navigating Climate Challenges as a Company17:50 Hiring for Data Roles: Insights for Founders19:20 Evolution of Data Science Roles in the Industry21:10 Advice for New Employees in Startups23:06 Lightning Round25:29 996 Startup Work CultureMore on Watershed: https://watershed.com/More on Tammy: https://www.linkedin.com/in/tammytseng/More on Sarah: https://www.linkedin.com/in/sarah-du/