Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
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Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
AI Is Killing the Agency Model (And How We're Using It to Win)
CEOs Unscripted
1 hour
1 month ago
AI Is Killing the Agency Model (And How We're Using It to Win)
In this compelling episode of CEOs Unscripted, host Jane Gentry sits down with Raj Choudhury, founder of Alloy Marketing and Purpose Group PE, to explore how purpose-driven leadership and strategic AI adoption are reshaping mid-market companies. š TIMESTAMPS: 00:00 - Introduction: From Uganda to Atlanta - Raj's Journey 03:45 - The Two Tracks: S1 (Blue-Collar Businesses) vs S2 (Agency Platform) 08:20 - What is The Purpose Playbook Framework? 12:15 - Open-Book Management: Why Transparency Wins 17:30 - The Four-Bucket Goal Framework (People, Quality, Brand, Financials) 23:45 - How AI is Disrupting the Agency Business Model 28:10 - Agentic Roles: The Future of Service Industries 33:25 - The Grieving Process: Managing AI-Driven Change 38:40 - Why Engineers Shouldn't Do Sales (And Other CEO Blind Spots) 42:15 - Creating Safe Environments for AI Experimentation 46:30 - Legal and Security Considerations for AI Implementation 51:20 - The Great Game of Business Integration 55:10 - Building Context in a Social Media World 58:45 - Naivety as a Superpower in Business 1:01:30 - The Language of Business is Numbers 1:03:15 - The 8-Minute Rule: When to Stop and Reset 1:05:45 - Final Thoughts and Where to Connect What You'll Learn: šÆ The Purpose Playbook Framework - How open-book management and transparent goal-setting create employee engagement and drive sustainable growth in blue-collar businesses š” AI Implementation Strategy - Moving beyond tools to transform business models: Why agentic roles are disrupting the traditional services industry and how to prepare your team š Breaking the Linear Growth Model - How AI is enabling agencies and service businesses to scale revenue without proportionally increasing headcount š Change Management in the AI Era - The "grieving process" employees need when core skills become automated, and how to guide teams through transformation Key Takeaways for Mid-Market CEOs:
ā The four-bucket framework (People & Product, Quality, Brand Awareness, Financials) that aligns every role from C-suite to shop floor
ā Why gamification and context matter more than compensation in driving performance
ā How to implement AI tools within established methodologies rather than letting technology dictate your processes
ā The critical difference between building for income versus building for wealth when positioning for exit Featured Topics:
- Private equity strategies for blue-collar businesses
- Open-book management and financial transparency
- Conscious capitalism in practice
- Agency business model disruption
- Agentic AI and synthetic roles
- Employee engagement through shared purpose
- Strategic change management
- M&A insights for service businesses Whether you're scaling a mid-market company, implementing AI initiatives, or exploring PE opportunities, this episode delivers actionable frameworks and unfiltered insights from a CEO who's been in the trenches.Ā š RESOURCES MENTIONED: The Purpose Playbook: The Definitive Guide to Building Your Team's Purpose, Vision, Tenets, & Values (PVTV) By Jeff Hilimire, Teresa Caro, and Megan Barney Companion guide to the Turnaround Leadership Series Tools & Frameworks Mentioned:
Writer.ai (AI-powered editing tool)
Google Gemini / Notebook LM
The Great Game of Business by Jack Stack RACI Matrix for decision-making 13-Week Cash Flow Forecasting
š Purpose Group Newsletter: purposegroup.substack.com š¤ ABOUT THE GUEST: Raj Choudhury is the founder of Alloy, a marketing agency serving mid-market technology brands, and Purpose Group, a PE firm focused on acquiring and transforming blue-collar businesses. With his partner Jeff Hilimire and co-founder David Cummings, Raj implements the Purpose Playbook framework across their portfolio companies, including Gerald Printing & Liberty Imaging. With 25 years of experience in M&A within the agency space, Raj brings unique insights into building sustainable, people-first organizations that scale profitably. ABOUT CEOs UN
CEOs Unscripted
Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
