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

Inside the first BizOps seat at Cogent Security (with Grace Hua)

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 Cogent 02:43 The Importance of People in Career Decisions 05:11 Navigating the Startup Landscape: Finding the Right Fit 07:06 Understanding the Cybersecurity Landscape 09:34 Building a Company from the Ground Up 11:43 The Role of Culture in Startup Success 13:59 Establishing Trust and Relationships in a New Role 16:31 Reflections on Time Management and Decision Making 17:46 A Week in the Life of a BizOps Leader at Cogent 21:28 Capitalizing on Opportunities with BizOps 22:47 Effective Interviewing Techniques 24:42 Closing Candidates in a Competitive Market 27:01 Key Qualities for Founding BizOps Roles 30:51 Leveraging AI for Enhanced Workflows 33:31 Rapid Fire

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]