The Story Behind the Strategy
What happens when an aspiring FBI agent with a criminal justice degree wakes up on graduation day and realizes he doesn't want that career after all? For Matt Green, this unexpected pivot led to a journey through finance and investment banking before he eventually co-founded Sales Assembly - a company now delivering skills training to thousands of B2B sales professionals across hundreds of tech companies.
In this revealing episode of The GAP, Matt Green draws from his unique vantage point to explore why the gap between sales training and execution persists. His perspective challenges conventional wisdom about sales methodology, training effectiveness, and what truly separates top performers from the rest. Matt's insights come from working with hundreds of B2B tech companies, giving him a bird's-eye view of patterns that most sales leaders miss while focusing on their own organizations.
Game-Changing Insights from Matt
The Methodology Myth
Most sales leaders get caught in an endless debate over which methodology will deliver the best results - MEDDIC, MEDDPICC, SPICED, or something else entirely. Matt turns this thinking on its head by asserting that consistency matters far more than which specific sales methodology you choose.
When teams follow a consistent approach, their work becomes measurable. This measurability creates the foundation for identifying what's working, what's not, and where targeted improvements can make the biggest difference. Without consistency, teams constantly reset, preventing the pattern recognition that drives improvement.
Filling the Skills Training Gap
Sales Assembly addresses a critical gap that Matt identified across the B2B tech landscape. While companies typically invest heavily in product training and process training (methodologies), they often neglect skills training - the fundamental capabilities that drive success regardless of product or process.
Through approximately 300 live training sessions annually, Sales Assembly teaches AEs to improve negotiation skills, helps CSMs master multi-threading techniques, and builds the core competencies that make any sales process work better. These skills-focused programs reach thousands of participants yearly and focus exclusively on execution rather than theory.
The Basketball Team Analogy
Matt uses a sports comparison that perfectly illustrates the relationship between methodology and skills. He likens a go-to-market team to a basketball team, where the sales leaders act as coaches developing the playbook (methodology). Sales Assembly fills the role of trainers - making sure players do their push-ups, sit-ups, and laps to develop the fundamental fitness needed to execute any playbook successfully.
This distinction helps explain why some organizations have solid methodologies but still struggle with execution. They've focused on designing the perfect plays without ensuring their team has the fundamental skills to run them effectively.
What Actually Makes Top Performers Successful
After observing countless sales organizations, Matt noticed a pattern in what separates star performers from the rest. Top reps rarely outperform because they follow methodology better than others. Instead, they excel at fundamental skills that work in any sales context: active listening, rapport building, and effective discovery questioning.
This insight helps explain why some salespeople consistently outperform others despite working within the same sales process - they've mastered the foundational skills that transcend any methodology. While mediocre performers focus on checking methodology boxes, top performers focus on customer connection and understanding.
The Three Universal Execution Gaps
After working with hundreds of sales organizations, Matt has identified three critical skill deficiencies that consistently undermine performance:
1. Discovery Deficiency
Discovery remains the most widespread weakness across all companies Matt encounters. Even sophisticated sales organizations struggle with this fundamental skill. Reps frequently rush through discovery, ask surface-level questions, and miss opportunities to uncover true customer needs. This gap exists regardless of industry, company size, or sales methodology.
2. Enterprise Selling Complexity
As more companies shift upmarket, teams that succeeded in mid-market sales find themselves unprepared for enterprise complexities. This creates immediate execution gaps in:
- Multi-threading into multiple stakeholders
- Navigating complex buying committees
- Managing longer, more sophisticated sales cycles
- Building consensus among diverse decision-makers
3. Customer Success Commercialization
The industry has rapidly shifted from viewing CSMs as project managers to expecting them to drive revenue. Matt describes this as "a mad dash over the past year and a half" to transform customer success teams into commercial engines. Most CSMs were hired for their domain expertise and project management skills - not their ability to spot expansion opportunities, negotiate renewals, or drive upsells.
The Forgetting Curve Problem
Perhaps Matt's most eye-opening insight explains why traditional training approaches fail to improve execution. He points to the "forgetting curve" - a phenomenon where people lose approximately 50% of training content within seven days without reinforcement. Even worse, if reps don't apply what they've learned within 30 days, they forget roughly 90% of the training.
This explains why one-off training sessions, regardless of quality, rarely translate to better execution. Without structured reinforcement through role-playing, coaching, and immediate application to real deals, most training investments simply evaporate.
Market Shifts in 2025
After weathering the challenging market of 2023, Matt sees distinct shifts in sales leader sentiment and priorities this year. The first half of 2024 showed cautious optimism, while the second half has demonstrated much stronger confidence. While conditions haven't returned to 2022 levels, they've become more consistent and predictable - allowing sales leaders to plan effectively again.
This stability has revealed three dominant priorities across the industry: developing enterprise selling capabilities, creating commercially-minded customer success teams, and fixing broken top-of-funnel processes. Additionally, Matt notes a significant return to in-person selling, with companies once again allocating travel budgets and prioritizing face-to-face meetings after years of remote-only approaches.
AI's Practical Impact on Sales
The conversation around artificial intelligence in sales has matured significantly. Rather than focusing on whether AI will replace sales roles (particularly SDRs), companies now look for ways AI can enhance productivity through numerous small improvements that add up to meaningful impact.
Matt sees three primary applications emerging: AI-powered practice platforms that allow reps to rehearse skills with automated feedback; efficiency tools that help smaller teams accomplish more; and reinforcement systems that help training stick by providing additional practice opportunities. The focus has shifted from replacement to enhancement - using AI to make humans better rather than obsolete.
The Value-in-Every-Interaction Principle
Exceptional salespeople distinguish themselves by providing genuine value in every customer touchpoint. Matt emphasizes that modern buyers conduct significant research independently and often don't engage with salespeople until they're close to making decisions.
Rather than simply "checking in" on proposals or following up on meetings, top performers find ways to deliver value whether or not a prospect buys. This might mean sharing relevant content, making introductions, or offering insights that help the prospect's business regardless of the deal outcome. Matt illustrates this with examples of sharing training resources or industry intelligence that benefits prospects even if they don't immediately move forward.
The Power of Peer Connection
One of Sales Assembly's most valuable offerings has nothing to do with formal training. Each month, they host peer group calls bringing together VPs of Sales and CROs from dozens of companies. These sessions create a rare space where sales leaders can bring challenges to peers experiencing similar issues without the pressure of pitching or posturing.
Matt occasionally invites non-member sales leaders to join these sessions as guests, recognizing that this type of collective problem-solving accelerates solutions and helps leaders avoid common pitfalls. The insights shared in these forums often prove more valuable than formal training because they address specific, timely challenges.
FAQs
1. Should we switch from MEDDIC to MEDDPICC (or another methodology)?
Probably not. Matt's experience across hundreds of companies shows that the specific methodology matters much less than applying one consistently. Constant switching creates confusion and prevents the pattern recognition needed to identify where real skill gaps exist. Pick an approach that fits your business, stick with it long enough to make it measurable, and focus your energy on building the skills that make any methodology successful.
2. Why do my top performers succeed when others struggle with the same process?
Look beyond methodology compliance to fundamental skills. Your top performers likely excel at the basics: effective discovery, active listening, proper qualification, and value articulation. These skills work in any sales context and with any methodology. Rather than forcing everyone to follow the same playbook identically, identify the underlying skills that drive your top performers' success and build training programs around those capabilities.
3. How do I make sure our training actually sticks?
Combat the forgetting curve with structured reinforcement. Implement role-playing exercises immediately after training. Schedule manager coaching sessions focused on specific skills. Create peer practice opportunities. Most importantly, ensure reps apply new skills to real deals within days, not weeks. Consider using AI tools that allow additional practice with feedback. Without this systematic reinforcement, even the best training program will fall victim to the forgetting curve. Looking to make your training stick? Explore how GTM Buddy can help you bridge the gap between training and execution
4. What should I focus on first if my team is struggling with execution?
Matt recommends starting with three foundational areas. First, improve discovery by teaching reps to ask better questions and truly understand customer needs. Second, strengthen qualification to ensure reps spend time with prospects who offer the best long-term value, not just anyone who might sign. Third, help your team provide genuine value in every interaction instead of just moving deals forward. These three skills form the foundation for better execution regardless of your specific methodology.
5. How is AI actually helping sales teams today?
Forget the hype about AI replacing salespeople. The practical applications focus on enhancement, not replacement. AI-powered platforms like Nooks allow reps to practice cold calling and receive automated feedback. Efficiency tools help smaller teams accomplish more by handling routine tasks. Training reinforcement systems provide additional practice opportunities beyond what managers can offer. The best AI applications in sales free humans to focus on what they do best: building relationships and understanding complex needs.
6. How can I learn from what other sales leaders are doing?
Join peer communities where sales leaders openly share challenges and solutions. Consider Sales Assembly's monthly calls, which bring together dozens of sales leaders in a no-pitch environment. These forums provide access to collective wisdom that's impossible to develop in isolation. Matt often invites non-member sales leaders to join as guests, creating an opportunity to learn from others' experiences without the usual networking pressures.
Subscribe to The GAP Podcast for more practical insights on bridging the gap between sales theory and real-world execution.
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TL;DR
- Consistency in methodology matters far more than which specific methodology you choose
- Skills training fills the gap most companies leave between product and process training
- Core sales skills like discovery and qualification drive results regardless of which methodology you use
- Without reinforcement, the forgetting curve erases 90% of training content within 30 days
- The same execution gaps-discovery, enterprise selling, and commercial CSMs-appear consistently across companies
- AI's most valuable role is enhancing human capabilities rather than replacing them
- In-person selling is making a comeback in 2024 and 2025
- Every customer interaction should deliver genuine value beyond just advancing your agenda
- Peer learning accelerates problem-solving by leveraging collective experience