The Thoughtful Entrepreneur 2222 - The Sales Strategy That Won't Leave You Out in the Cold with Alleyoop's Gabe Lullo
Why Modern B2B Sales Starts with Founders: Insights from Gabe Lullo of Alleyoop
On this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Gabe Lullo, CEO of Alleyoop, a leading B2B sales development company. Gabe dives into the critical strategies that modern founders and sales teams need to adopt—covering everything from founder-led sales and shifting lead generation tactics to building authentic engagement through personal branding. This episode is a goldmine for startup founders, sales leaders, and anyone aiming to scale their outbound strategy with more precision and impact.
Building a Modern B2B Sales Engine
Gabe emphasizes that founders must be on the front lines of sales early in their journey. Founders bring unmatched product knowledge and passion that resonates with early customers and helps shape go-to-market messaging. These firsthand sales experiences offer valuable insight into what prospects actually care about, allowing for real-time iteration and refinement. Gabe cautions against hiring a VP of Sales too early—founders need to establish a repeatable, scalable process before expanding the team.
In today’s sales environment, traditional cold emailing is losing its edge due to regulation and deliverability challenges. Gabe recommends a return to high-impact basics: cold calling and content creation. Phone calls allow for real-time, human interaction, while content—especially on LinkedIn—builds trust and positions founders as thought leaders. Gabe practices what he preaches with his consistent posting strategy and his podcast, Do Hard Things, which highlights authentic stories of grit and resilience.
Gabe also explains how Alleyoop helps B2B companies bridge the gap between marketing and sales. Their done-for-you systems manage appointment setting, lead qualification, and process optimization for clients ranging from startups to giants like Adobe and Zoom Info. For founders ready to scale their outreach, Gabe recommends focusing on authenticity, strategic connection building, and consistent engagement to generate high-quality pipeline.
About Gabe Lullo
Gabe Lullo is a seasoned entrepreneur and executive with deep expertise in sales, marketing, recruiting, and management. After graduating from the Barney School of Business at the University of Hartford, he launched his own sales, training, and marketing firm, which he successfully ran for over a decade. Gabe has also had a notable career in executive recruiting, expanding placements across IT, software development, sales, customer success, and executive leadership. As CEO of Alleyoop, he focuses on company culture, customer success, and scalable sales systems.
About Alleyoop
Alleyoop builds high-performing sales development systems for B2B clients. Their services include lead qualification, appointment setting, and outbound process design tailored for scalable growth.
Links Mentioned in this Episode
Episode Highlights
- Founders must lead sales to learn and iterate early
- Cold calling and content outperform traditional cold email
- LinkedIn content builds brand and trust
- Alleyoop connects marketing to sales with proven systems
- Authentic storytelling drives long-term engagement
Conclusion
Gabe Lullo delivers a compelling roadmap for building and scaling a sales engine rooted in authenticity, process, and founder-led momentum. His practical advice challenges conventional thinking and emphasizes the importance of doing the hard things that truly move the needle in B2B sales. For those looking to elevate their go-to-market strategy, this episode is a must-listen.
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