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

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.

Sponsored by

Next Level Growth - A proven system designed to help entrepreneurs scale their businesses with clarity, accountability, and the right strategic support to reach their next stage of growth.
Learn more: https://www.nextlevelgrowth.com/

Ever felt like your company is running in circles while you quietly burn out, stuck between drive and exhaustion?
This episode is a blunt, emotionally raw exploration with Lindsay Gibson, COO of TextNow, a leader who’s walked away from the grind, returned for redemption, and rebuilt both companies and herself from the inside out. Sivana Brewer dives deep with Lindsay into the shock of losing vision, the chaos of remote work, and the brutal clarity that comes only after you’ve crashed headlong into career “success.”
If you’re tired of vague leadership advice and want exclusive, no-BS strategies for authentic leadership, unclenching burnout’s grip, and making culture work for real teams, listen right now. Miss this, and you might repeat the pain Lindsay barely escaped. These lessons are battle-forged, urgent, and unlike anything the standard playbooks offer.

Timestamped Highlights
[00:01:11] – The brilliant but gritty origin of TextNow: solving real pain for people who have to choose between a phone bill and groceries
[00:02:45] – Why Lindsay left her COO seat (twice) and what chasing “interesting work” really costs
[00:04:34] – The BlackBerry “return rate” disaster: how fixing buyer’s remorse became a master class in real-world delegation
[00:07:49] – The shocking truth: Engineering wasn’t the problem—here’s what really derails a company’s goals
[00:10:11] – The brutal downside of remote-first culture… and the hardest part of rebuilding accountability across a fractured team
[00:14:32] – Motherhood, loss, and the hidden price of ambition: Lindsay’s real talk on the boundaries she’ll never break again
[00:19:04] – “Dead bodies in the process”—when leadership feedback stings and the rebirth of authentic management
[00:27:54] – Why remote teams lose their soul (and how one-on-one connection fights back against isolation)

About the Guest
Lindsay Gibson is the Chief Operating Officer of TextNow, a disruptive, ad-supported mobile carrier serving millions who demand true flexibility in mobile communications. With over two decades shaping iconic tech cultures, including a 16-year run at BlackBerry, she’s mastered the hard edge of scaling, comeback leadership, and authentic team connection. Known for leading through crisis and comeback, Lindsay is a straight-talker driven by integrity and obsession with growth.
🔗 LinkedIn | Website

Mentioned Resources
BlackBerry
ChatGPT
Cursor
Reclaim
T-Mobile
AT&T
“Burnout” (book)

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.

Ever secretly wondered if success, early retirement, a big exit, and the CEO chair are as good as it looks? What if the “dream” of ownership leaves you restless, searching for meaning, and itching to build again?
This episode pulls back the curtain on the real journey: Marcus Hantla, a relentless builder who’s seen both sides, reveals the wild emotional highs of exits and the raw, daily grind of COO life inside Contractor Foreman, a fast-growing SMB construction SaaS. He and Sivana get blunt about AI hype, hands-dirty delegation, and the gut-check moments that test even the toughest operators.
The stakes: Stop winging it in your own career, team, or transformation or risk getting left behind. Listen now to confront the myths of growth, find new ways to thrive, and get the gritty, exclusive playbook you won’t hear in sanitized TED Talks.

Timestamped Highlights
03:41 – What no one warns you about early retirement and the uncomfortable truth about waking up “free.”
06:43 – How a random plumber changed Marcus’s entire career (on his very own porch).
09:10 – The COO/CEO “deciding dance” and why true empathy is a secret growth weapon.
14:40 – Real talk: Losing a debate with the CEO (and why not every “brilliant” idea should win).
17:25 – AI sales calls, live demos vs. real humans—what actually works right now.
20:55 – Is the “beautiful” user interface dead? Why the next SaaS war is about simplicity, not design.
26:14 – The dangerous side of AI consensus: Can chasing “truth” kill the next big breakthrough?
35:03 – The sobering math of executive gratitude (and the crisis no leadership manual covers).

About the Guest
Marcus Hantla is the COO of Contractor Foreman, a leading construction management software platform engineered for small and mid-market builders and contractors. With 25+ years in construction and tech—plus multiple exits—Marcus is renowned for his hands-on leadership and hard-won insights at the intersection of trades, SaaS, and rapid growth.
🔗 LinkedIn | Website

Mentioned Resources
Cetdigit
Ask the Foreman (Contractor Foreman feature)
Google
ChatGPT
Reddit
Facebook
Giftology by John Ruhlin
Slack

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.

Sponsored by:
Genius Network - An exclusive community for highly successful entrepreneurs, connecting you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter.
Learn more: https://www.geniusnetwork.com/

What if the single greatest unlock for scaling your company has nothing to do with strategy, and everything to do with how much you care?

In this gut-level conversation, Sivana Brewer sits down with Amit Shah, COO of Virta Health, a company on a mission to reverse metabolic disease in a billion people. They reveal the raw mechanics, hard decisions, and emotional realities of building a culture where real feedback, personal mission, and relentless impact actually drive bottom-line results. Expect stories that challenge your comfort zone, a blueprint for turning skeptics into true believers, and a rare glimpse into what makes teams (and COOs) last a decade or more through hyper-growth.

If you’re tired of surface-level advice and want the proven, exclusive tools to protect your culture (and your soul) as you scale, hit play now. The risk of mediocre leadership has never been higher, and these lessons simply can’t wait.

Timestamped Highlights
[00:00] – The rebel truth about why people don’t care what you know until something shocking happens
[00:03:23] – Inside Virta’s billion-person mission and the radical evidence that built unwavering belief
[00:06:57] – The jeans, Disneyland, and moment a clinical trial changed thousands of lives
[00:13:17] – The single conversation that blew away a hardened healthcare skeptic
[00:17:13] – Why LIVE patient stories kick off every company meeting and what that does to culture
[00:21:24] – How Virta built a team that actually sticks (and outgrows their own roles)
[00:25:41] – When your job changes every 12 months: The hidden playbook for surviving hyper-growth
[00:33:24] – The care vs. candor tightrope—how to love your team while pushing for relentless results

About the Guest
Amit Shah is the Chief Operating Officer of Virta Health, where he leads growth, product development, and patient care delivery for a hyper-growth company that’s transforming metabolic disease care. With a track record spanning executive roles at Paladina Health, McKinsey, and Amazon, plus roots as a mission-driven entrepreneur, Amit is known for building high-performance teams that scale with heart and precision.
🔗 LinkedIn | Website

Mentioned Resources
Trulia
Zillow
Dr. Steve Finney
Dr. Jeff Volek
Dr. Hallberg
United Airlines
US Foods
Blue Shield of California
Alex & Layla Hormozi
Google Docs, Google Sheets, Google Calendar

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.

Ever feel overwhelmed by growth or haunted by the worry that your team’s success might derail the mission?
This is your inside pass. Sivana Brewer dives deep with Dan Murphy, COO of D1 Training, to uncover what really separates winning brands from chaotic burnout. From scaling a nationwide fitness franchise by 100+ units fast, to building a culture where passion crushes bureaucracy, and tough metrics make or break careers, this episode exposes the choices, pivots, and vulnerable moments every top operator faces.
Listen now if you want to avoid stalling your company’s growth, escape the COO loneliness trap, and get proven, unconventional takeaways on reinventing your playbook in a frantic market. This is real talk you won’t find anywhere else, straight from the second in command.

Timestamped Highlights
[00:01:01] – The wild origin story: Losing a pro career, the CEO’s game-changing invention, and how it launched a new franchise model
[00:03:39] – Why D1 threw out the playbook and planted flags everywhere plus what they learned scaling from 1 to 160 locations
[00:05:17] – The counterintuitive “avatar” that drives most revenue and why it’s probably NOT who you think
[00:09:57] – How the right “spark” can reveal your company’s true North—advice for COOs looking for their next big thing
[00:13:37] – The brutal scale-up pivot: When to walk away from side businesses, passive owners… and old friends
[00:16:11] – Outsourcing secrets, bringing it all back in-house, and the moment when cost control meets franchisee happiness
[00:21:28] – The biggest “aha” that changed their growth trajectory—what actually gets local buyers to care and buy in
[00:25:34] – When loyalty isn’t enough: Handling hard conversations with passionate, under-performing leaders
[00:27:48] – Managing egos, CEO/COO conflict, and why “freedom to dream” requires radical focus

About the Guest
Dan Murphy is the Chief Operating Officer of D1 Training, a national franchise leading the youth and community athletic training space. A former Division I soccer player and West Point graduate, Dan has decades of leadership experience spanning military and high-growth franchise operations. He’s known for his relentless execution, passion-driven leadership style, and community-building expertise helping D1 scale from a single Nashville gym to 160+ locations and counting.
🔗 LinkedIn | Website

Mentioned Resources
Will Bartholomew
Peyton Manning
Tim Tebow
Chris Paul
Exos
CrossFit
Ray Dalio’s “Principles”

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.

Sponsored by:
Redirect Health - Affordable healthcare benefits designed to make traditional insurance optional, with 24/7 access to primary care and Rx support that helps businesses reduce costs while keeping employees covered.
Learn more: https://www.redirecthealth.com/