<![CDATA[Early Access]]>https://riverside.comRiverside.fm (https://riverside.com)Mon, 02 Nov 2026 14:10:49 GMTWed, 17 Sep 2025 05:47:42 GMT60Sarah DuGo behind the scenes with the people who built it first - the founders and early hires of today’s fastest-growing startups. We dive into the bets they made, the mistakes, the wins, and everything in between!episodicSarah Dusarah@uncorkcapital.comno<![CDATA[Inside Clay's Scale from 85 to 600 (with Julia Govberg, Chief of Staff)]]>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.

Timestamps
00:00 Introduction to Julia and Clay

01:53 Journey from First Round Capital to Clay

04:30 Understanding the Chief of Staff Role

06:32 Quarterly Planning and Cross-Functional Collaboration

08:57 Scaling Challenges

10:45 Talent Acquisition Strategies

10:52 Leadership Dynamics and CEO Insights

11:03 Time Management and Prioritization

14:29 Transitioning from PLG to Enterprise Sales

15:55 Leveraging LinkedIn for Brand Growth

17:31 Building a Passionate User Community

19:57 Learning and Adapting in a Chief of Staff Role

25:15 Embracing Negative Maintenance as an Operating Principle

28:55 Quickfire Insights and Advice

]]>89678018-8f53-4003-b9d0-82ec614d25d9Tue, 06 Oct 2026 13:00:00 GMT<p>Join me in conversation with Julia Govberg, Chief of Staff at Clay.</p><p>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.</p><p><b><strong>Timestamps</strong></b><br />00:00 Introduction to Julia and Clay</p><p>01:53 Journey from First Round Capital to Clay</p><p>04:30 Understanding the Chief of Staff Role</p><p>06:32 Quarterly Planning and Cross-Functional Collaboration</p><p>08:57 Scaling Challenges</p><p>10:45 Talent Acquisition Strategies</p><p>10:52 Leadership Dynamics and CEO Insights</p><p>11:03 Time Management and Prioritization</p><p>14:29 Transitioning from PLG to Enterprise Sales</p><p>15:55 Leveraging LinkedIn for Brand Growth</p><p>17:31 Building a Passionate User Community</p><p>19:57 Learning and Adapting in a Chief of Staff Role</p><p>25:15 Embracing Negative Maintenance as an Operating Principle</p><p>28:55 Quickfire Insights and Advice</p>no00:32:33Inside Clay's Scale from 85 to 600 (with Julia Govberg, Chief of Staff)full<![CDATA[Inside dbt Labs' Run to $100M ARR (with Kaitlyn Henry)]]>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 Motherduck

02:39 Career Path: From Venture to Chief of Staff

04:48 The Role of Chief of Staff: Expectations vs. Reality

07:19 Prioritizing Projects as Chief of Staff

12:00 Measuring Success in the Chief of Staff Role

14:28 Scaling Companies: Lessons from dbt

17:00 Investing Insights: Operator vs. Investor Perspectives

19:31 Hiring Leaders: Building Effective Executive Teams

21:38 Post-dbt Fivetran merger

28:00 Transitioning to Mother Duck

29:49 Choosing the Chief of Staff Role

31:24 Lessons Learned from DBT

34:33 Building Trust with Executives

37:21 Navigating the AI Era at Mother Duck

]]>6615e0e0-9c59-44d5-a47c-0941832ddf20Wed, 02 Sep 2026 05:45:00 GMT<p>Join me in conversation with Kaitlyn Henry, Chief of Staff at Motherduck. </p><p></p><p>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.</p><p></p><p>Timestamps:</p><p>00:00 Introduction to Kaitlyn Henry and Motherduck</p><p>02:39 Career Path: From Venture to Chief of Staff</p><p>04:48 The Role of Chief of Staff: Expectations vs. Reality</p><p>07:19 Prioritizing Projects as Chief of Staff</p><p>12:00 Measuring Success in the Chief of Staff Role</p><p>14:28 Scaling Companies: Lessons from dbt</p><p>17:00 Investing Insights: Operator vs. Investor Perspectives</p><p>19:31 Hiring Leaders: Building Effective Executive Teams</p><p>21:38 Post-dbt Fivetran merger</p><p>28:00 Transitioning to Mother Duck</p><p>29:49 Choosing the Chief of Staff Role</p><p>31:24 Lessons Learned from DBT</p><p>34:33 Building Trust with Executives</p><p>37:21 Navigating the AI Era at Mother Duck</p>no00:40:42Inside dbt Labs' Run to $100M ARR (with Kaitlyn Henry)full<![CDATA[Building 0 to 1 AI Products at Nooks (with Alex Zhang)]]>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 Nooks

02:15 Career Journey: From DoorDash to Nooks

03:43 Understanding Nooks: The AI Sales Platform

06:30 Human vs. AI in Sales:

09:04 Transitioning from SaaS to AI Native Products

10:52 Creative Solutions: Using AI for Sales Training

12:33 Debugging AI Features: Identifying the Issues

13:14 Exploring AI Interaction and Latency Challenges

14:54 Expanding Product Surface Area

16:54 Growth and Evolution: Alex's Journey at Nooks

18:40 Lessons from "Failed" Products

22:08 Rapid Fire

]]>3b8d3097-f5a4-451d-a010-ade490e5834fWed, 08 Jul 2026 13:00:00 GMT<p>Join me in conversation with Alex Zhang, Nooks' first PM and now Group PM. </p><p></p><p>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.</p><p></p><p>Timestamps:</p><p>00:00 Introduction to Alex Zhang and Nooks</p><p>02:15 Career Journey: From DoorDash to Nooks</p><p>03:43 Understanding Nooks: The AI Sales Platform</p><p>06:30 Human vs. AI in Sales:</p><p>09:04 Transitioning from SaaS to AI Native Products</p><p>10:52 Creative Solutions: Using AI for Sales Training</p><p>12:33 Debugging AI Features: Identifying the Issues</p><p>13:14 Exploring AI Interaction and Latency Challenges</p><p>14:54 Expanding Product Surface Area</p><p>16:54 Growth and Evolution: Alex's Journey at Nooks</p><p>18:40 Lessons from "Failed" Products</p><p>22:08 Rapid Fire </p>no00:24:31Building 0 to 1 AI Products at Nooks (with Alex Zhang)full<![CDATA[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

]]>324b9163-1d9a-449a-8758-08c429f79367Wed, 03 Jun 2026 11:00:00 GMT<p>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.</p><p></p><p>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.</p><p></p><p>Timestamps:</p><p>00:00 Grace Hua's Journey: From McKinsey to Cogent</p><p>02:43 The Importance of People in Career Decisions</p><p>05:11 Navigating the Startup Landscape: Finding the Right Fit</p><p>07:06 Understanding the Cybersecurity Landscape</p><p>09:34 Building a Company from the Ground Up</p><p>11:43 The Role of Culture in Startup Success</p><p>13:59 Establishing Trust and Relationships in a New Role</p><p>16:31 Reflections on Time Management and Decision Making</p><p>17:46 A Week in the Life of a BizOps Leader at Cogent</p><p>21:28 Capitalizing on Opportunities with BizOps</p><p>22:47 Effective Interviewing Techniques</p><p>24:42 Closing Candidates in a Competitive Market</p><p>27:01 Key Qualities for Founding BizOps Roles</p><p>30:51 Leveraging AI for Enhanced Workflows</p><p>33:31 Rapid Fire</p>no00:36:32Inside the first BizOps seat at Cogent Security (with Grace Hua)full<![CDATA[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

]]>9ef8aae9-b19e-450b-9ea4-aa20f056814dMon, 02 Mar 2026 23:28:14 GMT<p>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.</p><p></p><p>Timestamps:</p><p>00:00 Introduction to Sarah Zeng and Her Journey</p><p>02:37 Transitioning from Investing to Startups</p><p>04:57 Joining Character AI</p><p>06:48 The Move to Braintrust</p><p>08:39 Effective Strategies for Chief of Staff Onboarding 10:03 Understanding Braintrust's Core Products</p><p>12:38 Navigating the Role of Chief of Staff</p><p>15:06 Growth in Consumer AI vs. Infrastructure AI</p><p>16:40 Braintrust's Rapid Growth and Market Position</p><p>19:20 Future of AI Evaluation and Observability</p><p>21:56 Rapid Fire</p>no00:26:04Inside Braintrust: Scaling a Category-Defining AI Evals Platform (with Sarah Zeng)full<![CDATA[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

]]>63f04986-08fe-4b7c-8a3f-12aa49a46f39Tue, 03 Feb 2026 01:00:00 GMT<p>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.</p><p></p><p>Olivia joined as the 5th employee. Two years later, GPTZero has grown to millions of users and $25M+ in revenue.</p><p></p><p>We cover:</p><p>🎨 Designing for trust in AI products</p><p>🧠 How students and teachers are really using AI</p><p>💬 Building culture inside a rocketship startup</p><p>&amp; more</p><p></p><p><b>Timestamps</b></p><p>00:00 Introduction to GPTZero and Olivia's Journey</p><p>01:51 The Role of a Product Designer at GPTZero</p><p>03:42 Building a Team and Initial Projects</p><p>05:22 Designing for Speed and Quality</p><p>06:49 The Evolution of Design Tools</p><p>08:26 Design Principles for Trust and Credibility</p><p>09:06 User Interaction with AI in Education</p><p>12:36 The Responsible Use of AI in Education</p><p>15:28 Scaling Company Culture at GPTZero</p><p>19:06 Moments of Realization and Responsibility</p><p>20:58 Lightning Round: Insights and Inspirations</p>no00:24:47Designing the Standard for AI Detection (with Olivia, GPTZero's First Product Designer)full<![CDATA[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

]]>65d47d6a-0682-4a8a-9ced-6373554dda66Thu, 06 Nov 2025 05:19:13 GMT<p>What does it look like to be the first BizOps hire at a company rebuilding banking from the ground up?</p><p></p><p>In this episode, I chat with <b>Charlie Liao</b>, who joined <b>Column </b>- founded by William Hockey, one of Plaid's co-founders - when the team was around 70 people.</p><p></p><p>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!</p><p></p><p>Timestamps</p><p>00:00 Introduction to Column and Charlie </p><p>01:05 Transition from Investing to Operations </p><p>02:53 Joining Column: The Decision Process </p><p>05:50 Navigating Startup Risks and Responsibilities </p><p>08:39 Defining Success in BizOps </p><p>10:41 Handling Ambiguous Projects </p><p>12:00 BizOps and Cross-Functional Collaboration </p><p>12:41 Importance of Documentation and Processes </p><p>14:00 Balancing Speed and Structure </p><p>14:42 Setting Boundaries in a Utility Role </p><p>15:49 Scaling the BizOps Team </p><p>16:54 When to Hire Your First BizOps Person </p><p>18:06 Qualities of a Great First Hire </p><p>19:46 Mindset for Quick Decision Making </p><p>20:23 Rapid Fire Questions and Closing Thoughts</p>no00:24:01Inside the First BizOps Seat at Column (with Charlie Liao)full<![CDATA[Inside Clay’s Marketing Engine (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://mattmaiale.substack.com/

https://x.com/maiale

]]>45314988-9f03-482e-ae11-8b557c6b30eeTue, 14 Oct 2025 20:08:09 GMT<p>When Matt Maiale joined <b>Clay</b>, the go-to-market platform helping sales teams find, enrich, and personalize outreach at scale, there were just five people and no marketing playbook.</p><p></p><p>Clay now serves thousands of customers and recently raised a $100M Series C at a $3.1B valuation.</p><p></p><p>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.</p><p></p><p>00:01 — Intro</p><p>00:55 — Matt’s path before Clay</p><p>01:56 — Finding &amp; evaluating Clay</p><p>02:53 — How Clay closed him</p><p>04:06 — Week 1 as first marketer</p><p>05:04 — Building the growth flywheel</p><p>05:28 — Fixing conversion</p><p>06:14 — ICP &amp; vertical focus</p><p>07:47 — Simple wins (Buy button, funnel fixes)</p><p>07:47 — Waitlist as a lever</p><p>10:08 — Messaging: startups vs. enterprise</p><p>11:40 — Defining the role</p><p>12:29 — “Bottoms-up marketing”</p><p>14:11 — Referrals &amp; community</p><p>15:57 — Spend philosophy</p><p>17:07 — Compounding growth channels</p><p>18:30 — Product education</p><p>20:07 — Emojis to describe Clay</p><p>21:45 — Culture bits</p><p>23:16 — Misconception: growth at all costs</p><p>24:18 — Hiring your first marketer</p><p>25:06 — Post-Clay travel</p><p>25:59 — What he’s building now</p><hr /><p>To learn more about Matt and what he’s working on:</p><p><a rel="noopener noreferrer nofollow" href="https://instantdomainsearch.com/" target="_blank">https://instantdomainsearch.com/</a></p><p><a rel="noopener noreferrer nofollow" href="https://mattmaiale.substack.com/" target="_blank">https://mattmaiale.substack.com/</a></p><p><a rel="noopener noreferrer nofollow" href="https://x.com/maiale" target="_blank">https://x.com/maiale</a></p>no00:27:27Inside Clay’s Marketing Engine (with Matt Maiale, Clay’s First Marketing Hire)full<![CDATA[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/

More on Tammy: https://www.linkedin.com/in/tammytseng/

More on Sarah: https://www.linkedin.com/in/sarah-du/

]]>4d2f6bed-ff43-4757-914a-b279aa9ca3e9Wed, 17 Sep 2025 07:04:24 GMT<p>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!</p><p></p><p>Timestamps:</p><p>00:00 Introduction to Tammy and Watershed</p><p>01:21 Choosing Watershed</p><p>03:28 Recruitment Insights: What Watershed Did Right</p><p>04:11 Transitioning from Quora to Watershed</p><p>05:20 First Days at Watershed: The 'First Day Ship' Tradition</p><p>06:34 Advice for Early Function Roles</p><p>08:01 Early Decisions and Their Long-Term Impact</p><p>09:15 Recognizing the Need for More Data Talent</p><p>10:17 Growing with Watershed: Retaining Early Talent</p><p>11:46 Navigating Career Transitions</p><p>13:35 Unlearning as the Company Scales</p><p>14:47 Key Moments in Watershed's Journey</p><p>15:55 The Role of Culture in Team Dynamics</p><p>16:18 Navigating Climate Challenges as a Company</p><p>17:50 Hiring for Data Roles: Insights for Founders</p><p>19:20 Evolution of Data Science Roles in the Industry</p><p>21:10 Advice for New Employees in Startups</p><p>23:06 Lightning Round</p><p>25:29 996 Startup Work Culture</p><hr /><p>More on Watershed: <a rel="noopener noreferrer nofollow" href="https://watershed.com/" target="_blank">https://watershed.com/</a></p><p>More on Tammy: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/tammytseng/" target="_blank">https://www.linkedin.com/in/tammytseng/</a></p><p>More on Sarah: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/sarah-du/" target="_blank">https://www.linkedin.com/in/sarah-du/</a></p><p></p>no00:28:16Lessons & Early Days Inside Climate Unicorn Watershed (with Tammy Tseng)full