Second in Command: The Chief Behind the Chief with Cameron Herold

What keeps a fast-growing company from losing its edge?
In this Fan Favorite episode, Cameron Herold sits down with Gaurav Agarwal, President and COO of ClickUp, to revisit one of the show’s most energizing conversations on leading at scale.
Gaurav went from banking in Singapore and Tokyo to running operations at a 1,000-person software company. He shares his first 90 days playbook, why ClickUp executes like it has no resources, and how he trains leaders to think like GMs.
Listen now.
Sponsored by:
AMP – a practical, proven methodology that helps teams move from trying to do more with AI to achieving more because of it, replacing fragmented experimentation with real AI Operations capability. Through personalized training, strategy, and hands-on support, teams get a clear path to build momentum and embed AI into daily work. Learn more here.
Timestamped Highlights
00:00 What Separates Legendary Businesses
02:36 ClickUp’s Vision: One App to Rule Them All
05:05 The #1 CRM on G2 Is Not HubSpot
10:26 From India to Seattle
15:25 The Engineering Mindset for Business
18:01 The First 90 Days
25:34 Plan Big, Execute Lean
27:53 Training Leaders to Think Like GMs
36:05 The Taj Hotel Lesson on Core Values
38:48 Advice to His Younger Self
About the Guest
Gaurav Agarwal is President and COO of ClickUp, the everything app for work. At the time of this recording, he was COO, having joined as chief growth officer. Before ClickUp, he was SVP of growth at Freedom Financial Network and CMO at Molekule. His background spans banking, e-commerce, hardware, fintech, and SaaS.
Mentioned Resources
ClickUp
Molekule
Barclays
G2
HubSpot
Starbucks
Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance – The World’s Leading Community for Seconds in Command
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

What does it take to turn a 150-person agency into an AI-first company?
In this episode, our co-host, Lindsay Smith, sits down with Lior Eldan, co-founder and COO of Moburst. Lior has helped brands like Google, Samsung, and Uber grow, and has led five acquisitions along the way.
Lior shares how he runs a remote team across continents, why he shares company numbers openly, and how AEO is changing the way brands get found.
Listen now.
Sponsored by:
Genius Network, an exclusive community for highly successful entrepreneurs that connects you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter. Learn more here.
Timestamped Highlights
00:00 AI and the Future of Agency Operations
02:54 A Day in the Life of a COO
06:15 Managing a Global Remote Team
12:12 Transparency with Company Numbers
15:59 The Acquisition Playbook
21:34 Building an AI-First Agency
25:47 Choosing the Right AI Tools
29:26 Build vs. Buy: The Acquisition Strategy
34:13 The Full-Funnel Marketing Difference
38:49 AEO: The New SEO
46:42 From HR Officers to Agency Founders
48:01 The CEO-COO Dynamic
50:22 What’s Next for Moburst
About the Guest
Lior Eldan is co-founder and COO of Moburst, a global digital marketing agency with about 150 people. He leads operations, hiring, financial metrics, and data infrastructure. Under his leadership, Moburst has worked with Google, Samsung, Uber, Reddit, and Pfizer, and has completed five acquisitions.
Mentioned Resources
Moburst
Slack
Asana
Claude
ChatGPT
Gemini
Perplexity
About the Co-Host
Lindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer. She previously scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug, Stop Branding, Start Experiencing, and helps leadership teams use experience as a competitive growth lever.
Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance – The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command, Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

What if your job posting was designed to push the wrong people away?
In this Fan Favorite episode, Cameron Herold sits down with Tod Melnyk, former second in command at Martell Media and now its CEO, to revisit one of the show’s most candid conversations on hiring and culture.
Tod went from 18 years at Labatt Breweries to running the business behind Dan Martell’s brand. He shares how Martell Media hires, why culture beats experience, and how to say no to a visionary CEO.
Listen now.
Sponsored by:
Redirect Health, one of our gold Strategic Partners, offers healthcare benefits that make health insurance optional. It is a 24-hour online primary care and RX membership that guides employees before problems happen. Learn more: redirectcoo.com
Timestamped Highlights
00:00 The Polarizing Job Posting
04:33 From Labatt Breweries to Entrepreneurship
07:29 Inside Martell Media’s Interview Process
11:21 “You Had Me at the First Slide”
14:36 The Three Core Values
21:09 Hiring Gen Z for Culture Fit
25:03 The Media Engine and the Revenue Engine
28:17 Saying No to a Visionary CEO
38:13 “Show Me Your Calendar and Your Bank Account”
45:09 Advice to His Younger Self
About the Guest
Tod Melnyk is CEO of Martell Media and AI Venture Studio. At the time of this recording, he was second in command to Dan Martell, running the business behind Dan’s media brand and revenue. He spent 18 years at Labatt Breweries, rising from sales rep to regional director. He then invested in and built craft breweries and ran operations for a European car service business.
Mentioned Resources
Dan Martell
Buy Back Your Time
Labatt
EOS Worldwide
Predictive Index
Starbucks
HeyGen
Lime
Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance – The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command, Unleash the Power of Your COO Book
Claim your FREE copy: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

What does it take to build a global team from scratch when a pandemic hits weeks into your new job?
In this episode, our co-host, Lindsay Smith, sits down with Awa Kone, Head of Finance at Caliza. Awa previously served as COO of Corridor and as global head of operations at Flutterwave.
Awa shares why she never expects the fires to stop, how she works with a CEO without being a yes-woman, and what it takes to keep a culture intact across continents.
Listen now.
Sponsored by:
Cadre AI - If you are ready to turn AI into real growth for your business rather than just more tools, visit Cadre AI, our Gold Partner, to discover how their team helps companies increase revenue, improve profitability, and implement AI that truly delivers results: https://www.cadreai.com/coo
Timestamped Highlights
02:44 Early Life in Ivory Coast & Actuarial Career
06:42 Joining Flutterwave During COVID
08:09 Building Remote Teams in a Pandemic
12:29 Scaling Infrastructure Without Breaking
14:30 Working With the CEO as Second in Command
17:56 Fire Prevention vs Firefighting in Operations
19:54 Different Titles, Same Core Role
25:30 Maintaining Culture Across Global Markets
29:29 Team Retreats and Face-to-Face Connection
32:48 Training and Onboarding in Startups
About the Guest
Awa Kone is Head of Finance at Caliza, a global operator who helps high-growth companies build the operational and financial infrastructure to scale without breaking. She previously served as COO of Corridor and spent five and a half years at Flutterwave as global head of operations, where she built and scaled teams, treasury operations, and critical infrastructure through a period of extraordinary growth. She holds an MBA from MIT Sloan, is a Fellow of the Society of Actuaries, and has built her career across the US, Europe, and Africa.
Mentioned Resources
Flutterwave
MIT Sloan School of Management
Swiss Re
Milliman
PwC
Society of Actuaries
Slack
Zoom
WhatsApp
Invest In Your Leaders
About the Co-Host
Lindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer. She previously scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug, Stop Branding, Start Experiencing, and helps leadership teams use experience as a competitive growth lever.
Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance – The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command, Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

What does it take to go from Chief of Staff to running your own business unit before turning 30?
In this Fan Favorite episode, Cameron Herold sits down with Melisa Tokmak, former General Manager of Document AI at Scale AI and now founder of Netic, to revisit one of the show's most insightful conversations on building teams and leading fast.
Melisa's path is rare: a tiny village in Turkey, Stanford, Facebook, then right hand to Scale's CEO. She breaks down what a chief of staff really does, how she wins over senior candidates when she is younger than most, and why doing everything yourself is the hardest habit to break.
Whether you are building a team or chasing a bigger role, this conversation is a masterclass in taking the elevator. Listen now.
Sponsored by:
STS Capital Partners - Your expert guides on the journey to an Extraordinary Exit™. To learn more about STS Capital Partners and how they achieve maximum value by Selling to Strategics™, check out here.
Timestamped Highlights
05:48 Attracting Top Talent
08:42 Leadership Development
11:20 Transitioning to Scale AI
14:40 Defining Chief of Staff
18:59 Overcoming Growth Challenges
22:33 Focusing on Priorities
26:02 Hiring and Culture
30:04 Identifying Candidates
33:33 First Principles Approach
36:40 Career Advice and Closing
About the Guest
Melisa Tokmak is the founder of Netic. At the time of this recording, she was General Manager of Document AI at Scale AI, where she led a team of engineers, machine learning scientists, and product, operations, sales, and marketing talent building fine-tuned models for logistics, financial services, healthcare, and government. She joined Scale two years out of college as Chief of Staff to CEO Alexandr Wang, then founded the company's government unit, whose customers included the U.S. Army, the Defense Innovation Unit, and the U.S. Air Force.
Mentioned Resources
Scale AI
Stanford University
Meta (Facebook)
1-800-GOT-JUNK?
Defense Innovation Unit
Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance – The World's Leading Community for Seconds in Command
Get Cameron's book: Second in Command, Unleash the Power of Your COO Book
Claim your FREE copy: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi