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

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 Speaker A 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/

Ever question if you’re truly moving the needle in a high-stakes, fast-growth role or just treading water in chaos?
In this unfiltered replay, Cameron Herold gets radically real with Asana’s COO, Anne Raimondi, a powerhouse operator with a track record scaling iconic SaaS brands from eBay to Zendesk. Their candid conversation delivers hard-hitting truths and breakthrough strategies for COOs, VPs of Ops, and ambitious seconds-in-command. From conquering boardroom friction to onboarding at scale, and from navigating imposter syndrome to wielding conscious leadership, this episode is your no-nonsense roadmap to building culture, resilience, and runaway growth.
The window for operational greatness closes quickly. Don’t risk getting left behind as your competitors dial in these proven systems. Press play now for a front-row seat to rare, real-world tactics you won’t hear anywhere else.
Timestamped Highlights
[00:00] – Why this Asana episode is a record-breaking, fan-favorite comeback
[00:03:02] – The one skill that built Anne’s “uncommon” career and why she doubled down on curiosity
[00:05:33] – A dot-com crash, a diamond startup, and how obsession with customer pain points kept Anne in the tech arena
[00:07:47] – Is product obsession really the COO’s unfair advantage? Anne reveals what sets true ops leaders apart
[00:13:14] – How Anne’s onboarding at Asana destroyed all her old assumptions about exec transitions
[00:15:10] – The joy of “extra delights”—what most SaaS products miss about human motivation
[00:25:34] – The real source of company politics (and how transparency kills it dead)
[00:44:38] – Anne’s most vulnerable answer: How she faces down imposter syndrome and wins

About the Guest
Anne Raimondi is the Chief Operating Officer of Asana, a global leader in work management software empowering teams to orchestrate their work with clarity and impact. With 20+ years scaling technology giants, including senior roles at Zendesk, TaskRabbit, SurveyMonkey, and eBay, Anne brings deep boardroom and operational wisdom to fast-growth SaaS. She’s also a lecturer at Stanford Graduate School of Business and has served on the boards of Gusto, Patreon, and more. Anne is renowned for her mission to build workplaces that blend high performance with humanity.
🔗 LinkedIn | Website

Mentioned Resources
Facebook
Microsoft Project
Blue Nile
eBay
TaskRabbit
Guru (knowledge management)
SendGrid
Gusto
Patreon
Block
ThredUp
15 Commitments of Conscious Leadership (framework/book)
Stanford Graduate School of Business
Kozmo (Seattle delivery)

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

Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.

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.

When was the last time you felt your vision misunderstood, your partnership undervalued, or your operational roadmap tangled? If you’re a COO wrestling with translating big ideas into real impact, this conversation is your lifeline.
Sivana Brewer welcomes Stephanie Kauffman, Chief Operating Officer at Melanoma Research Alliance, for an urgent episode that lifts the veil on what actually moves the needle for COOs. From converting financial “legends” into game-changing board allies to crafting story-driven partnerships that triple outcomes, you’ll hear how real-world translation builds trust fast, drives innovation, and prevents career-stalling burnout.
Press play now. Don’t risk getting stuck in your leadership bubble. Every minute here arms you with exclusive, proven techniques to connect, influence, and scale before someone else beats you to it.

Timestamped Highlights
[00:10] – A stunning perspective shift: why “second in command” is really “dual in command” for COOs everywhere
[00:02:25] – The myth of melanoma: deadliest form of skin cancer, massive underestimation, and breakthrough facts COOs should know
[00:08:21] – Surprising everyday tips for preventing melanoma beyond just sunscreen (plus one you’ve likely never heard)
[00:10:39] – How legendary finance leaders shaped Stephanie’s radical “private equity” nonprofit strategy—what every COO can steal
[00:18:49] – The $12.7 million secret: bold partnerships that defied board skepticism (and the power of gaming for social impact)
[00:27:11] – Data-driven storytelling for buy-in: How Stephanie translates emotional conviction into actionable board wins
[00:31:47] – Professional translation: the vital COO role in turning CEO vision into operational clarity for every stakeholder
[00:43:15] – The “3 Bs” formula and simplifying the complex: brief, brilliant, be done—your solution to communication chaos

About the Guest
Stephanie Kauffman is Chief Operating Officer of the Melanoma Research Alliance, the world’s largest nonprofit funder of melanoma research. Known for high-impact storytelling and cross-industry partnership wins, she previously held SVP roles at Universal Studios and Breast Cancer Research Foundation. Stephanie is recognized for translating visionary ideas into scalable operations, bringing decades of experience across finance, media, and biotech.
🔗 LinkedIn | Website

Mentioned Resources
Breast Cancer Research Foundation
Blizzard Entertainment (Overwatch partnership)
Universal Studios (media/partnerships)
Leverage Finance Fights Melanoma platform
UPF apparel (sun protection clothing)
Mafia Wars (gaming partnership)

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.