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14 - Building a Revenue-on-Demand Engine with Gabe Lullo

5 to 50: Financial Strategies for Growing Companies

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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:
  • How to build mental resilience in sales by categorizing objections into 10 core buckets
  • Why does it take 90 days to properly establish sales development campaigns
  • How to balance aggressive growth with financial sustainability
  • The framework for diversifying client portfolios: maintaining 40% enterprise and 60% SMB clients for stability
  • Why organic content marketing is replacing traditional sales collateral
  • Implement the "democratic leadership" approach when driving organizational change
  • The 15-20% revenue guideline for sales and marketing spend
  • Why leveraging content over cold calls can accelerate sales cycles
  • How to transition from an individual contributor to a leader by shifting focus


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:
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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