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

Revenue Rehab

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 She warns that outdated playbooks and one-way automation are leaving revenue on the table, while today’s buyers self-educate and expect immediate, meaningful interaction.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 technologies that identify and engage buyers earlier—well before they submit a form—by leveraging intent signals, enabling frictionless conversations, and reducing reliance on traditional gates. This proactive approach captures more of the market and improves the probability of converting ready buyers.

The Rapid-Fire Round

1. Finish this sentence: If your company has this problem, the first thing you should do is _ “Measure it. Find out how many balls are getting dropped. Quantify the problem so you can actually solve it and measure success.” — Maddie Bell
2. What’s one red flag that signals a company has this problem—but might not realize it yet? “You’re pushing out a lot of one-way communication, and buyers aren’t converting—or when they finally respond, you’re too slow to engage. If buyers ignore your outreach or you fail to respond within 1–2 minutes, that’s a big sign.”
3. What’s the most common mistake people make when trying to fix this? “Chasing new cool solutions instead of fixing today’s problems—like slow or missing follow-up. Start by solving existing gaps to create quick pipeline wins before adding new tools.”
4. What’s the fastest action someone can take today to make progress? “Start more conversations—and use AI for fair, objective, helpful buyer interactions that move them to the next step, ideally a team meeting. But don’t rush the process; let AI qualify and route effectively.”

Buzzword Banishment

Buzzword Banishment: Maddie’s buzzword to banish is "speed to lead." She dislikes this term because, in her view, it has become disconnected from what buyers actually want. Maddie argues that organizations have reduced "speed to lead" to a KPI or automated process—like quickly assigning a lead to a rep or sending out email sequences—rather than prioritizing a meaningful, timely first conversation that aligns with the buyer's needs and expectations. She advocates replacing it with "speed to first conversation" to ensure engagement is genuinely valuable to the buyer.

Links:

• LinkedIn: https://www.linkedin.com/in/maddiebell/

• Podcast: https://www.scheduler.ai/nextgen-gtm-podcast

• Business: https://www.scheduler.ai

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