How Ben joined Pearl and the 'dumpster' pitch

What would happen if you finally ditched micromanagement and actually let your teams run wild, faster, riskier, and more creative than you’d ever dare on your own?

Ben Plomion, COO of Pearl AI, joins Sivana Brewer for a sharp, no-fluff deep dive into the gritty reality of leading in markets where mistakes happen fast and growth is non-negotiable. Drawing from cross-functional battle scars in marketing, ops, and tech, Ben unpacks how he leveraged his CMO chops to become a next-level COO, why most leaders fail at “connecting the dots,” and exactly how he’s turning AI into his secret weapon for culture and operational scale.

If you’re tired of theory and ready for the untold COO playbook that frees you from indecision, protects you from hidden traps, and gives you unfair access to what the best operator-leaders are actually doing, listen now. Stalling means losing team trust, missing radical growth, and getting left behind.

Timestamped Highlights

[00:03:42] – The shocking “dumpster” pitch that clinched Ben’s COO job—would you take this text?

[00:05:10] – Connect the dots or die: Why leaders who only skim the surface always lose big

[00:07:26] – Zero in-house finance, outsourced chaos—how Ben plugged the leaks before it was too late

[00:10:51] – From chief cook to master delegator: The brutal art of giving up “employee benefits” and focusing where it matters

[00:14:42] – CEO second-in-command: The secret archetypes and why most COOs get it wrong

[00:18:29] – CMO to COO crossover: The superpowers that every operator should steal from marketing

[00:21:23] – Ditching values for operating principles—radical new rules for building a creative, AI-savvy team

[00:32:19] – “Let them run”: The unorthodox motto that keeps Ben’s teams breaking the rules, beating churn, and staying ahead

About the Guest

With over two decades of experience in marketing, commercial and operational leadership across Artificial Intelligence, Computer Vision, and Blockchain, Ben Plomion is the Chief Operating Officer at Pearl—the leading AI Software-as-a-Service (SaaS) company in dentistry. Prior to Pearl, he served as Chief Marketing Officer at Dibbs, an Amazon-backed tokenization-as-a-service (TaaS) platform. He was previously Chief Growth & Marketing Officer at GumGum, where he played a pivotal role in advancing AI-driven contextual advertising. Earlier in his career, Ben led global digital media efforts at both Magnite and GE Capital. A Forbes contributor and trusted advisor to companies like Deanna.ai, PebblePost, and #Paid, he is also a committed educator in the realms of AI, marketing, and Web3.

🔗 LinkedIn | Website

Mentioned Resources

• GumGum
• Anthropic Claude
• ChatGPT
• HubSpot
• Google Drive
• OKR (Objectives & Key Results)
• Amazon “70% data principle”
• Get Scalable by Ryan Deiss

About the Co-Host

Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.

🔗 Connect with Sivana on LinkedIn

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

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

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