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

Ep. 608 - FAN FAVORITE | YPO President and COO Sean Magennis - Lead With a Servant's Heart
What does it take to lead an organization of 27,600 CEOs across 135 countries while still leading with a servant's heart?
In this Fan Favorite episode, Cameron Herold sits down with Sean Magennis, former International Chairman of the Entrepreneurs' Organization (EO) and former President and COO of YPO, now EVP at Scouting America, to revisit one of the show's most insightful conversations on peer leadership.
Sean's path is rare: he bootstrapped his own business from South Africa to Canada with no debt and no laptop, then spent over two decades immersed in confidential peer groups before helping run one of the largest CEO communities in the world.
They get into how YPO's confidential "Forum" model teaches CEOs to speak from experience rather than give advice, why businesses evolve through life stages the same way people do, and the exact habits that keep his partnership with YPO's CEO in sync.
Listen now.
Sponsored by:
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Timestamped Highlights
00:00 YPO and the Mastermind Landscape for Entrepreneurs
02:10 Sean Magennis: From EO Forum Committee to YPO
07:15 The Volunteer Addiction: 23 Years of Peer Group Leadership
10:05 Inside YPO Today: 27,600 Members and $9 Trillion in Member Sales
13:40 The Forum: YPO's Confidential Peer Group Model for CEOs
16:20 How YPO Teaches Vulnerability and Builds Trust Among CEOs
19:00 Forum in Business: Bringing Peer Principles to the Workplace
27:00 How Businesses Evolve Through Lifecycle Stages Like Humans
36:20 Sean's Key COO Skills: Ego Management, Coaching, and Coordination
43:00 The CEO-COO Partnership and Sean's Biggest Lesson
About the Guest
Sean Magennis is EVP at Scouting America. At the time of this recording, he was President and COO of YPO, the global community of chief executives, where he led alongside a 27-year YPO member CEO and a board of 17 CEOs overseeing 27,600 members in 135 countries. He began his career in South Africa before moving to Canada in 1990, where he bootstrapped an organizational development and executive search business across Canada, the US, and Mexico, and served as past International Chairman of the Entrepreneurs' Organization (EO).
Mentioned Resources
Entrepreneurs' Organization (EO)
Dow Limited
College Pro Painters
Fortune's Best Places to Work list
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 happens when a company builds its growth strategy around reviving forgotten small towns instead of chasing the next big metro?
In this episode our co-host, Lindsay Smith, sits down with Nick Murphy, COO of Optomi Professional Services, a 100% US based technology firm operating through two brands: Optomi, which delivers high-end IT staffing, and Provalis, which brings IT and business process consulting to centers of excellence in rural America.
He built his career across investment banking, a decade at The Home Depot, and a senior finance role at Ibotta before joining Optomi in 2023 and being appointed COO in December 2025.
Together they get into the exact criteria Provalis uses before betting on a town, how one Wall Street Journal feature turned into a wave of national press, and why Nick says his people are the closest thing his company has to inventory.
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 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
0:00 — Staying Close to the Business
0:44 — Nick Murphy Introduction
6:25 — "Business Partners First, Finance Partners Second"
10:41 — Wall Street Journal Feature
12:10 — "A Company of Firsts"
13:25 — Untapped Talent in Rural America
15:56 — Revitalizing Main Street
20:08 — Paying 100% of Benefits
29:43 — Most Exciting Career Moment
33:08 — "Executive Amnesia" and the CEO Relationship
34:15 — Challenging the CEO
40:05 — "If I'm the Bottleneck, We've Got a Busted Process"
41:50 — AI as a Growth Vector
46:16 — Childhood Dream: School Bus Driver
About the Guest
Nick Murphy is COO of Optomi Professional Services, where he oversees both the Optomi staffing brand and the Provalis managed services brand. He built his career across investment banking with SunTrust Robinson Humphrey, nearly a decade at The Home Depot spanning finance, merchandising, e-commerce, and marketing, and a senior finance role at Ibotta. He joined Optomi in 2023, built out FP&A, marketing, PR, and enterprise strategy, and was appointed COO in December 2025.
Mentioned Resources
SunTrust Robinson Humphrey
The Home Depot
Ibotta
Wall Street Journal
Fox Business
News Nation
Newsweek
cooalliance.com/freebook
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
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 sit at the right hand of three different CEOs, back to back, and make each partnership work?
In this Fan Favorite episode, Cameron Herold sits down with Laurie Aaron, former Chief of Staff at AT&T and now founder of Arron Coaching, LLC, to revisit one of the show's most clarifying conversations on a role almost nobody truly understands.
Laurie's path is rare: 30 years inside AT&T and three successive CEOs gave her a front-row seat to how the chief of staff role must reinvent itself with every leader. She breaks down what separates a chief of staff from a COO and an executive assistant, and why the best ones prevent problems the CEO never even sees.
Whether you're wondering if you need a chief of staff, or wondering if you already are one, this conversation demystifies the role end to end. 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 Why the Chief of Staff Role Is So Misunderstood
02:10 The Origins: From the Military to the Corporate World
04:30 What Every Effective Chief of Staff Has in Common
07:15 Chief of Staff vs. COO: Where the Roles Diverge
10:05 My Right Hand and My Left Hand: Chief of Staff vs. Executive Assistant
13:40 How Title Inflation Diluted the Role
16:20 What Chiefs of Staff Are Actually Paid
19:00 Writing Who Has Your Back?
21:30 Can Any C-Suite Leader Have a Chief of Staff?
24:15 Where the Best Chiefs of Staff Really Come From
27:00 Why You Should Look Internally First
30:10 Building the Interview Squad
33:45 How Trust Gets Built Between a CEO and Their Chief
36:20 The Handshake Meeting: Setting the Vows
39:50 Knowing When and How to Challenge a CEO
43:00 Coaching CEOs and Chiefs of Staff as a Team
45:30 Speak Yourself Into the Room: Laurie's Advice to Her Younger Self
About the Guest
Laurie Aaron built her expertise on the chief of staff role over 30 years at AT&T, where she served as chief of staff to three different CEOs in succession. She is now the founder and CEO of Arron Coaching, LLC, a trusted advisor and executive coach to C-Suite leaders and chiefs of staff, and the author of Who Has Your Back?: A Leader's Guide to Getting the Support You Need by the Chief of Staff You Deserve.
Mentioned Resources
Who Has Your Back?
Hit The Ground Running
AT&T
The Misunderstood Role of the COO
cooalliance.com/freebook
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

Most operators never learn to fight autopilot, the quiet enemy of excellence.
In this episode, Lindsay Smith sits down with Mike Fedorov, COO of Applied AI Labs. With 26 years in operations and supply chain, as a former Accenture Director and Mars operations leader, Mike built his reputation staying on-site, in the detail, close to where the work breaks.
He shares his philosophy that a COO's first job is to keep the lights on, and the second is to keep them on better, explaining why flat structures are replacing layers of management, how AI works best as a coordination layer, and the defining power of mentorship in his career.
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™, complete the inquiry form here: https://stscapital.com/coo-alliance/
Timestemped Highlights
00:00 The Future of Flat Organizational Structures
01:44 What Applied AI Labs Does
02:38 The COO's Real Job: Keep the Lights On, and Better
05:11 A COO Who Watches Two Operations at Once
08:08 Scaling After Excelling: The Contractor Approach
09:18 Why Flat Structures Are Replacing Layers of Management
11:01 What Big Companies Get Right About Operations
12:45 Nimbleness vs. Routine: Autopilot as the Enemy of Excellence
16:06 How AI Actually Helps Operations: The Coordination Layer
18:44 AI as a Copilot, Not a Replacement
20:06 AI in Recruiting: What Works and What Fails
27:34 Defining Moments: The Power of Mentorship
30:52 How to Find and Structure Mentorship
38:55 What's Next for Applied AI Labs
43:55 Personal Growth: Knowing What You Don't Know
About the guest
Mike has 26 years of experience in operations and supply chain, as a former Accenture Director and, before that, leading operations planning and execution for Mars. He has run and turned around operations for some of the most complex and demanding companies in the world, and has saved major clients that were ready to walk. He leads engagements the way he has always worked: on-site, in the detail, close to the people who know where the work breaks. Operators trust Mike because he has done their job.
Mentioned Resources
Mars
Accenture
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
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

How do you walk into a company of nearly 800 people as its first-ever president and win over the ones who wanted your job?
We are bringing this one back because it keeps landing with second-in-command leaders. Cameron sits down with Sameer Kazi, the first president in ActiveCampaign's history, who joined a fast-growing company of nearly 800 people and had to earn trust from day one.
Sameer traces his path from employee 200 at ExactTarget through the Salesforce acquisition, KKR, Bessemer, and running Cheetah Digital, then unpacks how he split responsibilities with the CEO, why he brings non-finance leaders close to the numbers, and how he decides with incomplete information.
If you are stepping into a senior seat or scaling a business without losing its edge, this one is worth the revisit. Listen now.

Sponsored by:
This episode is brought to you by our Silver Sponsor, Next Level Growth.
They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.
If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.
Complete the assessment here to get started - nextlevelgrowth.com/cooassessment

Timestamped Highlights
02:35 Employee 200 at a "tiny little company" called ExactTarget
03:15 Filing an S-1 in 2008, right as the markets fell apart
03:50 Why the growth never actually slowed down
05:37 The years between Salesforce and ActiveCampaign
08:50 Walking into KKR and asking, "Barbarians at the Gate?"
10:38 The boardroom lesson from a business with declining growth
12:38 What an MBA is actually good for
13:38 Reading Salesforce's income statement before SaaS was cool
14:48 The 54% lever that only works while growth holds
15:52 Quitting his job to raise money with twins on the way
16:32 Why ActiveCampaign came looking for him
19:23 Why the role was never about empire building
21:46 Winning over the people who wanted his seat
25:11 How you know when you know enough to decide
26:24 What ActiveCampaign really does
34:47 Why every non-finance leader should learn the numbers
37:25 The advice he would give his 21-year-old self

About the Guest
Sameer Kazi was serving as President of ActiveCampaign at the time of this recording, the first person to hold that title in the company's history, reporting to founder and CEO Jason VandeBoom. A veteran SaaS operator, he was an early executive at ExactTarget (employee 200) through its acquisition by Salesforce and ran EMEA operations from London. He later served as interim CEO of Simply Measured and CEO of Cheetah Digital, and worked alongside investors including KKR and Bessemer. He holds an MBA and describes himself as a sleeves-rolled-up, sweat-the-details operator. Sameer is now the Chief Executive Officer at Pantheon Platform.
🔗 LinkedIn
Mentioned Resources
ActiveCampaign
Salesforce, formerly ExactTarget
Simply Measured - acquired by Sprout Social
Cheetah Digital - now Marigold
KKR
Bessemer Venture Partners
Experian
Silversmith Capital Partners
True
Cisco
Zapier
1-800-GOT-JUNK

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

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 is your first listen or a revisit, there is 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.

Sponsored by:
This episode is brought to you by our Silver Sponsor, Next Level Growth.
They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.
If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.
Complete the assessment here to get started - nextlevelgrowth.com/cooassessment