5 to 50: Financial Strategies for Growing Companies
14 - Building a Revenue-on-Demand Engine with Gabe Lullo
August 26, 2025
In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Gabe Lullo, CEO of Alleyoop, to explore his journey from SDR to CEO and the lessons learned while scaling a 150-person revenue-on-demand company. Gabe shares insights on balancing rapid growth with financial discipline, diversifying client portfolios, and building scalable systems without compromising quality. He also reveals why investing 15–20% of revenue in sales and marketing can drive sustainable success and how leveraging content over cold calls builds trust and accelerates sales cycles. A must-listen for entrepreneurs scaling service businesses.
In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Gabe Lullo, CEO of Alleyoop, to explore his journey from SDR to CEO and the lessons learned while scaling a 150-person revenue-on-demand company. Gabe shares insights on balancing rapid growth with financial discipline, diversifying client portfolios, and building scalable systems without compromising quality. He also reveals why investing 15–20% of revenue in sales and marketing can drive sustainable success and how leveraging content over cold calls builds trust and accelerates sales cycles. A must-listen for entrepreneurs scaling service businesses.


What you will learn:


Gabe Lullo
is the CEO of Alleyoop, a revenue-on-demand partner helping brands like Adobe, Bevy, and ZoomInfo scale with confidence. Rising from SDR to CEO, Gabe has built deep expertise in enterprise software sales, people operations, and revenue generation. At Alleyoop, he has grown the team to 150+ employees while pioneering scalable, content-driven sales strategies. As host of the Do Hard Things podcast, Gabe shares insights on sustainable growth, client partnerships, and building resilient, high-performing sales organizations.


Episode Resources:
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Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

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