Gap Prospecting Training: The Modern Prospecting System for Today’s Outbound
From the creators of Gap Selling — the method that redefines how teams build pipeline.
People We Work With:
Why Gap Prospecting Exists
Connect rates that once hit 70% are now under 4%. Email replies hover between 1–5%. Even booked meetings fall through at record rates.
Outbound activity keeps climbing because technology makes it easy. Dialers, sequencing tools, and AI allow sellers to reach thousands of buyers in minutes.
BUT, a majority of outbound, especially at high volume, fails to capture buyer attention or spark real conversations. Many teams focus on sending more instead of understanding what’s breaking their approach.
Gap Prospecting was built to fix that. The training teaches sellers and leaders how to identify the gaps in their outreach, target the right problems, and build a pipeline that consistently converts.
What Is Gap Prospecting
Gap Prospecting applies the principles of Gap Selling to the very first touch. It gives sellers a repeatable way to create curiosity, earn replies, and connect with buyers through relevance and problem understanding.
Instead of relying on scripts or volume, sellers learn to identify what’s happening in the buyer’s world: what’s changing, what’s breaking, and why it matters. That context becomes the foundation for effective outreach across calls, emails, and social.
What You’ll Learn
Gap Prospecting Training is built around two focused modules that give sellers the skills and structure to succeed in today’s outbound environment. Each session blends live instruction with practical exercises and real examples that make prospecting easier to apply and repeat.
Module 1: Rules of the Game
- The nine “truthbombs” of prospecting
- Why modern prospecting is failing
- How to deeply understand your buyers
- How to build your value proposition around problems, impacts, and root causes
- How to target the perfect buyers
- The two sales that 90% of sellers miss
- How to adopt the mindset of a top prospector
Module 2: Doing the Job
- How to use to refine, research, and enrich your lead lists
- Cold calling openers and talk tracks that still work in 2026
- How to turn pushback & objections into interest
- How to write cold emails that light up your buyer’s brain
- Where LinkedIn, events, mail, in-person, and referrals can add to your efforts
- How to bring this all together in sequences that get responses instead of blocks
- What causes no shows & exactly how to prevent them
- How to set yourself up for consistent success by managing your inputs
Each module builds on the next, creating a complete system sellers can use to drive consistent, high-quality pipeline.
Is Gap Prospecting Right for Your Team?
Every sales team’s outbound challenges look different. Let’s talk about where your pipeline is breaking and whether this training fits your goals.
Why It Works
Gap Prospecting is grounded in how buyers actually make decisions. It replaces generic messaging and activity-heavy tactics with outreach that connects to real business problems and creates urgency from the first touch.
The framework is built on three key elements that drive consistent results:
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Problem-Centric Messaging – Every call and email is built around the buyer’s world, highlighting the problems your solution was designed to solve.
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The Two Sales Framework – Sellers learn to create curiosity first, then interest, earning attention before asking for action.
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Evidence-Based Practice – Messaging and outreach techniques are drawn from live buyer data, ensuring teams focus on what actually earns responses.
Teams trained in Gap Prospecting report higher reply rates, stronger meeting quality, and measurable increases in top-of-funnel conversion.
Who It’s For
Gap Prospecting is built for revenue leaders and teams responsible for building pipeline that converts. The training equips sellers to prospect with relevance and equips leaders to measure and scale the results.
Designed for:
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CROs and VPs of Sales – Create a reliable top-of-funnel system that supports forecasting and growth targets.
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Sales Development Leaders – Improve connect rates, meeting quality, and conversion without adding more activity.
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Enablement and Training Teams – Reinforce consistent prospecting behaviors tied to measurable performance outcomes.
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Revenue Operations – Align outreach strategy with data, segmentation, and buyer insights for more predictable results.
Whether you manage a team of SDRs or oversee full-funnel performance, Gap Prospecting provides a common framework for building stronger, more consistent pipeline.
Your Trainer
Gap Prospecting Training is led by Will Aitken, one of the most recognized voices in modern sales and a co-creator of the Problem-Centric approach to outbound.
Will has spent years teaching sellers how to cut through noise and reach buyers with relevance. As the host of The Sell Better Show and co-founder of Sales Feed, he’s known for making complex sales concepts simple, actionable, and grounded in the real challenges revenue teams face every day.
He works directly with Keenan and the ASG team to deliver Gap Prospecting Training year-round — helping teams apply the principles of Gap Selling to the front of the funnel and turn outbound into a consistent source of pipeline growth.
Results and Outcomes
Teams that adopt Gap Prospecting see measurable improvement across every stage of outbound performance. Reps gain confidence in their outreach, leaders gain visibility into what’s driving engagement, and pipeline quality improves as a result.
Common outcomes include:
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Higher reply and connect rates across channels
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Fewer no-shows and stronger first meetings
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Clearer messaging alignment between sales and marketing
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Increased conversion from first conversation to opportunity
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More predictable, reliable pipeline growth quarter over quarter
The difference shows up fast — in the quality of outreach, the relevance of conversations, and the consistency of pipeline generation.
Ready to Rethink Outbound?
Gap Prospecting is the blueprint for a new era of top-of-funnel.