When Your Buyers Are Ready to Engage You’re Dropping the Ball

This week on Revenue Rehab, Brandi Starr is joined by Maddie Bell, CEO and Co-founder of Scheduler AI, who believes “the real risk isn’t in the dark funnel—it’s failing to deliver when the buyer finally raises their hand.” In this episode, Maddie challenges the industry’s obsession with “speed to lead,” urging revenue leaders to prioritize “speed to first conversation” with AI-driven, buyer-centric engagement. She warns that outdated playbooks and one-way automation are leaving revenue on the table, while today’s buyers self-educate and expect immediate, meaningful interaction. Will Maddie’s call for rethinking the moment of engagement change your strategy—or change your mind? Episode Type: Problem Solving Industry analysts, consultants, and founders take a bold stance on critical revenue challenges, offering insights you won’t hear anywhere else. These episodes explore common industry challenges and potential solutions through expert insights and varied perspectives. Bullet Points of Key Topics + Chapter Markers: Topic #1: Dark Funnel Obsession—Are Revenue Teams Focusing on the Wrong Problem? [01:10] Maddie Bell argues that while the industry is fixated on the challenges of the dark funnel and invisible buyer research, the true risk lies elsewhere: "The real risk isn't what you can't see, it's what you fail to act on when the buyer finally makes themselves known." She challenges CMOs and CROs to shift resources away from just uncovering hidden intent and instead ensure their processes and tech are ready for the critical moment buyers raise their hand. Brandi aligns with this shift, probing what readiness really entails and how companies can retrain their focus accordingly. Topic #2: Personalization at Scale—Why Automation Isn’t Enough [13:36] Maddie claims that traditional personalization methods—triggered email sequences and static nurture paths—have reached their limits due to the sheer number of signals and permutations needed. She challenges the industry to move beyond guessing with automation: "It's just really hard to personalize for a person without asking them about themselves again, without starting a two-way conversation." The discussion centers on the need for AI-driven, dynamic conversations to achieve true personalization, not just more sophisticated drip campaigns. Topic #3: AI as the Connector—Transforming Handoffs and Sales Structure [28:38] Maddie boldly asserts that AI agents are poised to revolutionize not just engagement, but the very structure of sales teams and revenue processes. She explains, "If you have the AI routing, you can create intelligent loops that essentially solve the leak across the pipeline..." prompting leaders to rethink their approach to sales specialization, handoff rigor, and marketing-sales alignment. Brandi challenges the scalability and organizational implications, sparking discussion on how revenue leaders should sequence process improvement before layering on AI. The Wrong Approach vs. Smarter Alternative The Wrong Approach: “I think they look for solutions to new things rather than solving problems that again, they already have. Right. Because at the end of the day, if we’re already making buyers wait hours, days, if we follow up at all, just solving that in the near term is going to get you a measurable pipeline win now without having to re redo and try all this new stuff that you don’t really know where it’s going to go.” – Maddie Bell Why It Fails: Chasing after new, untested solutions distracts teams from addressing the core issues already affecting buyer engagement. If companies ignore existing process gaps—like long response times—they miss out on immediate revenue gains and risk investing in initiatives that may not address their current challenges. The Smarter Alternative: Focus first on quantifying and solving existing friction points in the buyer journey, such as reducing wait times and ensuring prompt follow-up. By tackling these proven problems, organizations can unlock measurable wins and lay a stronger foundation before experimenting with new tools or strategies. The Most Damaging Myth The Myth: “The moment they raise their hand visibly is the start of the process.” – Maddie Bell Why It’s Wrong: Many go-to-market teams treat the buyer’s visible hand-raise—like filling out a form—as the beginning of engagement. But as Maddie points out, buyers actually start their process much earlier, often spending significant time researching and self-educating long before giving up their information. This myth leads companies to ignore the vast majority of prospects who never fill out a form (97%), missing opportunities to start conversations earlier and losing out on pipeline growth. What Companies Should Do Instead: Recognize that the buying journey begins well before formal hand-raising. Invest in strategies and ...