LeaderbookAI

A customer wants to spend more, but your revenue model gives you a reason to say no. Brent Hagan, Chief Supply Chain Officer at Lob at the time of recording, joins Felicia Shakiba to discuss how that tension exposed a gap between the company's metrics and the value customers needed. They examine operating-model change, manufacturing partnerships, AI-enabled scale and the personal cost of executive success.

IN THIS CONVERSATION

• Recognizing when subscription metrics obscure customer value

• Building credibility for change through early operating wins

• Connecting culture, accountability and decision ownership

• Reshaping manufacturing partnerships around dependable capacity

• Using AI for scale, consistency and materials routing

• Reconsidering ambition, health and family priorities

CHAPTERS

00:00 The customer deal Lob initially refused

00:38 Introducing Brent Hagan

01:10 Subscription metrics versus manufacturing economics

05:44 Challenging the business model from inside

09:42 Building credibility through quick wins

11:50 Leadership changes, culture and accountability

15:18 Clarifying decision ownership

18:06 Reshaping manufacturing partnerships

26:08 Using AI for scale, not just cost

28:17 AI-powered materials routing

29:58 The family letter that changed Brent's priorities

34:19 When career success stops feeling like success

37:14 Are your metrics aligned with customer value?

ABOUT THE GUESTS

Brent Hagan is the Chief Supply Chain Officer at Lob. In this conversation, he shares his experience changing the company's operating model and manufacturing network.

Backlight CEO Kathleen Barrett explains why customers can love your products while your business still struggles to scale. She shares how she focused an acquired portfolio, rebuilt sales quotas and financial visibility, and why leaders need to fix their operating foundations before layering on AI.

IN THIS CONVERSATION

• Why customer love isn’t the same as a scalable growth engine
• How to focus go-to-market investment across an acquired portfolio
• How to build trust when some products receive more investment than others
• Why leadership hiring requires both trust and a bias check
• The hidden cost of misaligned sales quotas
• Why AI-ready media workflows begin with organized content and trusted metadata

ABOUT THE GUEST

Kathleen Barrett is CEO of Backlight, a media technology company building products for media creation, management, distribution, and monetization.

Connect with Kathleen Barrett on LinkedIn
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Learn more about Backlight: https://www.backlight.co/

ControlUp CEO Jed Ayres and Chief Product Officer Gadi Feldman share the decision to bring 400 employees to Dubai while the company was operating through war and crisis—and what happened to morale, trust, and connection afterward.

IN THIS CONVERSATION

• How leaders make decisions during war and crisis

• Why 400 employees were brought together in Dubai

• What changed when distributed teams met in person

• How flatter organizations affect trust and accountability

• Where AI can improve employee experience and support

• How AI may reshape jobs, roles, and organizational structure

CHAPTERS

00:00 Introduction to Jed Ayres and Gadi Feldman

08:33 Leading during war and crisis

11:03 The decision to fly 400 employees to Dubai

12:57 Unifying dispersed teams across countries

15:07 Building trust through physical presence and culture

17:05 Moving from hierarchical to flat organizations

19:00 Balancing support and overstepping as a leader

20:10 Listening strategies in leadership

22:27 One-on-one leadership and employee growth

24:14 Debate and innovation in Israeli culture

25:56 The future of flat, empowered organizations

28:47 Using data to improve employee experience

33:01 AI in IT support and automation

36:10 Preparing for the future of work with AI

ABOUT THE GUESTS

Jed Ayres is CEO of ControlUp. Gadi Feldman is Chief Product Officer of ControlUp.

Explore more episodes: https://leaderbook.ai/podcast

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Welcome to a new era of the Leaderbook AI podcast. Everyone is talking about AI, but no one is talking about what’s actually happening behind closed doors. In this upcoming mini-series, host Felicia Shakiba brings you into the tight executive meetings where the real decisions, heavy trade-offs, and brutal moments happen.

We are cutting through the fluff and buzzwords to bring you conversations with real CEOs, executive teams, and investors who are putting AI to work inside real businesses.

Listen as we ask the hard questions:

Expect sharp 30-minute interviews to start, gradually moving into deep, one-hour in-studio recordings.

Subscribe, turn on notifications, and share this series with anyone leading through this massive moment of change. Grab your cocktail of insights—the mini-series kicks off next week!

Private equity portco CEO Jeremy Jones uses cultural alignment for due diligence in private equity — not financials — as the first filter in every acquisition. The result: Frazier & Deeter has grown from 530 to 850 people in seven months through three deals, with a fourth closing next week.

Jones walks through the three-year decision process behind the firm's partnership with General Atlantic, why his CPO sat in all 25 to 30 PE meetings and called HR counterparts at existing portfolio companies, and what the first 24 hours post-acquisition actually looks like for employees who found out the night before. He also addresses the hardest question in people-first PE strategy: is culture a trade-off against financial performance, or the operating system that produces it?

For PE operating partners, portfolio company CEOs, and leaders navigating acquisition, organizational design, and AI workforce strategy.

00:00 The Journey of Due Diligence in Private Equity

09:47 Cultural Alignment in Acquisitions

16:30 Day One Post-Acquisition

23:56 Defining Success Beyond Financials

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Tina Murphy, CEO at GHX, breaks down why talent is her top three priorities — not strategy, not capital — how GHX restructured its entire organization to get closer to customers and move faster, what she's looking for in leaders today that she wasn't three years ago, and why the companies that fail the AI transition won't fail loudly. They'll fail silently, quarter by quarter, until the gap becomes permanent.

00:00 The People Project: AI Transformation and Leadership

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We create high-performing powerhouses.

Private equity has had it easy for forty years. Cheap money, expanding multiples, and a rising S&P produced returns almost regardless of what firms did with the assets they bought. That era just ended — and Lee McCabe, Partner at Claymore Partners, argues most firms haven't adjusted to what replaces it. Lee spent years inside eBay, Expedia, Facebook, and Alibaba before joining a New York PE firm as an operating partner, and he's now built the operational platform he believes PE actually needs.

Chapters:

00:00 The Evolution of Private Equity

We create high-performing powerhouses.

Robin Goad, AWS executive, has been in the AI space since 2014—long before it was a boardroom priority. As Global Public Sector Industry Solutions GM at AWS, she's watched the hype cycles repeat, the barriers shift, and the use cases mature. Her read on where AI actually creates value for leaders is sharper—and more honest—than most of what you're hearing right now.

What do you mean, "I'm a CEO... and now I'm coding?"

Georg Ell, CEO of Phrase, hadn't written code since he was 15. Then his CFO demoed a custom-built app — and Georg felt "utterly inadequate." That evening he downloaded Claude. Six weeks later: 200,000 lines committed, 8 apps built, and a radically different understanding of what leadership means in the AI era.

Chapters:

00:00 The Awakening: Realizing the Need for Change

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We create high-performing powerhouses.

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Spencer Penn evacuated his engineer from Ukraine the day before Russia invaded. What he did next — and why it worked — reveals more about leadership trust than most books on the subject.

Penn is CEO and co-founder of LightSource, a procurement AI company that grew from two people in a garage to 64 employees. In this episode, he traces the company's origin to a $30 billion problem he watched firsthand at Tesla — car parts sourced via spreadsheets and email — and the moment he hired a Ukrainian developer off GitHub who would later need to get out of the country overnight.

Penn and Felicia Shakiba debate whether Elon Musk could have been even more successful with a different leadership approach, what separates mature from immature leadership mindsets, and a reframe on strengths that most leaders get completely backwards: the capability that comes easiest to you is almost certainly your highest ROI — and most people are blind to it.

Chapters:

00:00 The Genesis of LightSource

04:35 Finding the First Believers

14:45 Building Trust Through Adversity

19:15 The Gift of Opportunity

21:54 Balancing Leadership Decisions

24:15 The Importance of Values in Leadership

25:58 New vs. Experienced Leaders

29:15 The Complexity of Leadership Traits

31:55 The Impact of Leadership Style

36:30 Strengths vs. Weaknesses in Leadership

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