Why the Middle Layer of Your Agency Org Chart May Not Survive AI with Jennifer Bagley | Ep #841

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Are you still thinking of AI as just “ChatGPT with a better prompt”? Or maybe you’ve played around with Zapier automations and thought, yeah, that’s good enough. Today's featured guest knows that the agencies pulling ahead right now are building full-on AI agent networks that replace routine tasks, streamline data pipelines, and give their teams superpowers. She’s re-engineering her agency around AI and will talk about where she finds top-tier talent and why you don’t need to code to lead your agency into the future.

Jennifer Bagley is the CEO and founder of CI Web Group, a fully virtual digital marketing agency registered in 22 U.S. states with clients across the United States and Canada. A former corporate operator turned entrepreneur, Jennifer started in real estate and mortgage brokerage before leaning into the marketing work she built to support those businesses. Today she runs a modern, tech-forward agency that’s rebuilt its stack around AI, centralized data, and agentic networks, all while carrying the scars and lessons of scaling, pivoting, and re-founding a business from the ground up.

In this episode, we’ll discuss:

• Feeling trapped by the business.

• Hiring, firing, and the people reset

• AI, reskilling, and the end of “middle” roles

• What does this talent cost?

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Sponsors and Resources

E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.

From Corporate Ladder to Accidental Agency Founder

Jennifer came from an operations background, a self-proclaimed black belt in Six Sigma and certified project manager. Having built that corporate background, she had made a promise to herself (“by 30 I’ll be an entrepreneur”), and started to build the side hustle that became the main event. She started in real estate and mortgage brokering where she had to learn marketing the hard way; not because she wanted to be a marketer, but because the survival of her businesses depended on it.

Initially, Jennifer didn’t set out to build a scalable agency; she built a team to support her broker network. When the market collapsed in 2008, the same team that did marketing for agents suddenly had a market outside real estate. That “we’ll just help this painter or HVAC company” phase is where the web group was born: small, service-focused, and useful to people in her network. That accidental turn became a business by solving real, pressing problems for paying clients, then leaned into that.

Trading Time for Freedom: The Hard Pivot

For the first five years, Jennifer describes the business as a “lifestyle” operation, profitable maybe, but trapping her time. She was trading billable hours for income and was reaching her limit when she hired a coach that forced a reckoning: if entrepreneurship isn’t buying you time, money, and freedom, what’s the point? So she made the brutal choice of cutting consulting contracts and burning the bridge to the “safety” of hourly work, and effectively gave herself a mulligan.

This is the classic founder pivot: you have to choose between growth that keeps you doing the work and growth that scales the business without you. Jennifer’s reset wasn’t pretty, for a while she lost everything and she and her son lived in an office for a while, but it bought her the permission to build something salable, not just sustainable. Agency owners who feel trapped in delivery need to remember that sometimes you have to give up short-term revenue to create long-term value.

Feeling Trapped by the Agency and Becoming a CEO

Those first five years, Jennifer continued to run a business that started as a supply chain consulting and eventua