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Flip The Script Series – Gap Sell Keenan Live Pitches

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Hand pressing a “scale” button with connected icons of people, representing how to scale a sales team with structure.

How to Scale a Sales Team in 2025

Before scaling a sales team, sales leaders need to confirm the organization is ready to support more people, more process, and more pipeline. Hiring too early, without structure or visibility, creates...

Business figure with magnifying glass over a person icon, symbolizing sales enablement aligned to rep execution.

How to Align Sales Enablement with Execution

Most sales enablement programs aim to improve performance, but few deliver lasting change. Training is deployed, content is created, and tools are rolled out, yet reps still struggle to execute the...

Padlock with a glowing red checkmark, symbolizing sales behaviors that build buyer trust through credibility

5 Buyer-Backed Sales Behaviors That Drive Trust

ASG’s buyer survey confirms what many reps still get wrong: buyers don’t care about liking the seller. They care about whether the rep understands their business, asks the right questions, and offers insight...

Silhouette of a person surrounded by red checkmarks, representing what buyers expect from modern B2B sales reps.

5 Things B2B Buyers Expect from Sales Reps in 2025

ASG’s 2024 buyer survey reveals critical gaps between how sales teams sell and how buyers want to be sold. The data highlights execution issues across discovery, outreach, and demo performance that directly...

Three ascending bars with a red upward arrow, symbolizing measurable sales training impact on performance metrics.

How to Measure Sales Training Impact

Sales training only works when it improves execution in live deals. Effective programs help reps run better discovery, qualify accurately, control deal movement, and close with consistency. The result should...

A fork in the road with one illuminated, arrow-marked path representing the choice of an effective sales training program.

How to Choose a Sales Training Program

Sales training is one of the most important investments for improving execution in the field. The goal is to help reps run better discovery, qualify deals more accurately, and control opportunities from start...

Red neon plug connected to performance meter with bar graph and speed dial, symbolizing sales enablement powering execution

Sales Enablement Is Not a Learning Function

Sales enablement is often misunderstood. In many organizations, it has become a content distribution function measured by training completions, LMS logins, and certification rates. These metrics do not reflect...

5 Ways to Reinforce Sales Training in Live Deals

Reinforcement is the most overlooked step in sales training. It determines whether new skills are applied or forgotten. Without daily inspection and reinforcement, reps return to old habits and pipeline...

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Hand pressing a “scale” button with connected icons of people, representing how to scale a sales team with structure.

How to Scale a Sales Team in 2025

Before scaling a sales team, sales leaders need to confirm the organization is ready to support more people, more process, and more pipeline. Hiring too early, without structure or visibility, creates...

Business figure with magnifying glass over a person icon, symbolizing sales enablement aligned to rep execution.

How to Align Sales Enablement with Execution

Most sales enablement programs aim to improve performance, but few deliver lasting change. Training is deployed, content is created, and tools are rolled out, yet reps still struggle to execute the...

Padlock with a glowing red checkmark, symbolizing sales behaviors that build buyer trust through credibility

5 Buyer-Backed Sales Behaviors That Drive Trust

ASG’s buyer survey confirms what many reps still get wrong: buyers don’t care about liking the seller. They care about whether the rep understands their business, asks the right questions, and offers insight...

Silhouette of a person surrounded by red checkmarks, representing what buyers expect from modern B2B sales reps.

5 Things B2B Buyers Expect from Sales Reps in 2025

ASG’s 2024 buyer survey reveals critical gaps between how sales teams sell and how buyers want to be sold. The data highlights execution issues across discovery, outreach, and demo performance that directly...

Two red mittens stick out of the snow, with one holding a small wooden stick that displays a sign reading "HELP!" The image humorously illustrates the struggle and misalignment in sales conversations, where buyers often feel lost or unsupported. This emphasizes the blog's focus on addressing buyer challenges and guiding them effectively to prevent stalled deals and churn.

Keys to Preventing Stalled Deals

Sales teams aren’t losing deals because of bad pitches or tough competition — they’re losing because buyers and sellers aren’t on the same page about the real problem. 48% of buyers say they’ve bought the...

A red and black horseshoe magnet attracts red cubes while leaving other colorful cubes scattered below, visually representing the importance of attracting the right customers rather than chasing every deal. The image reflects the concept of strategic, problem-focused selling to avoid churn and build long-term retention.

Sell to Retain, Not to Hit Quota

It’s that time of year again. The deals you thought were dead suddenly come back to life. Buyers who ghosted for months resurface and sales floors are buzzing with that familiar, frantic energy. Your sales...

hand-drawn style illustration of a stick figure stacking blocks into a pyramid structure on a grid-paper-like background. The stick figure is lifting a block to place it on the topmost level, symbolizing building or constructing something. The sketch is surrounded by scribbled edges, adding to the casual and conceptual style of the artwork

How to Build Trust Through Buyer-Centric Actions

Whether we like it or not, buyer-seller relationships are built on trust, yet, many of the behaviors observed in modern sellers erode that trust. Buyers are looking for someone who is credible. They couldn’t...

Aligning Discovery With Buyer Needs

Salespeople are missing a crucial opportunity. Buyers enter the sales process looking for help – guidance in understanding their challenges, clarity on their goals, and insight into potential solutions. Yet,...

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Balance Sheets Exploring their Hidden Sales Secrets

Balance Sheets: Exploring their Hidden Sales Secrets

Decoding Balance Sheets for Sales Growth Last week, we went through the Profit and Loss Statement.  This week we’re going to tackle the balance sheet.  The balance sheet and the profit and loss statement go...

Social Selling - How To Use LinkedIn Properly

Social Selling – How To Use LinkedIn Properly

Last week we talked about why it’s vital to not use LinkedIn as a cold selling platform. A bunch of you didn’t agree and wanted more on the right way to use LinkedIn and social selling to further your sales....

What a Killer Deal Strategy Looks Like

What Your Deal Strategy Must Include

Getting your prospect engaged, getting them on the proverbial hook is critical to selling. Prospecting is the holy grail of sales and it get’s a lot of attention as it should. To most of us, finding and...

Tell Your Customer "No"! During Prospecting

Tell Your Customer “No”! During Prospecting

Here’s the deal. When you’re prospecting, leads can be demanding, They will ask for a lot, but it doesn’t mean you have to say yes every time.   Can you tell your customer or prospect...

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Blogs

MEDDPICC vs Gap Selling

Comparison: MEDD(P)ICC and Gap Selling

Put yourself in the shoes of a buyer. You’re looking to buy some new software. One of the potential vendors subscribes to the MEDDIC sales methodology. You schedule a call, and during the call, the sellers...

Keenan and a salesperson engaged in a conversation about active listening and consultative selling as they discuss the principles of Gap Selling.

Gap Sell Keenan 63: Stop Selling and Listen

We can’t say this loud enough, B2B sales is changing. Relentlessly pushing products and hammering prospects with your rehearsed sales pitch is dead. Developing a successful sales approach needs to focus on...

Risk to Reward A Sales Case Study

Risk to Reward: A Sales Case Study

How a Calculated Sales Risk Paid Off One of the top selling Tequilas in the world doesn’t allow the word tequila to be used when referring to it’s product. Yes, it’s on the bottle, but that’s pretty much the...

Sales Strategy Lessons From My 14 Year Old Self

Sales Strategy Lessons From My 14 Year Old Self

The Sales Strategy that Made a Skatepark a Reality This is how my feisty 14 year old self accidentally Gap Sold my town into building a skatepark. Buckle up! Because I’m going to walk you through my...

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EBooks

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Blogs

MEDDPICC vs Gap Selling

Comparison: MEDD(P)ICC and Gap Selling

Put yourself in the shoes of a buyer. You’re looking to buy some new software. One of the potential vendors subscribes to the MEDDIC sales methodology. You schedule a call, and during the call, the sellers...

A man in casual work attire is precariously sawing off a large branch from a tree, the very branch he's sitting on, symbolizing a 'sales demo' mistake. The background reveals a hazy industrial skyline, contrasting with the tree's lush foliage, emphasizing the short-sighted actions that can undermine long-term goals, reflective of the pitfalls in customer engagement and sales promises

Avoiding a Common Sales Demo Mistake

We’ve all been there. You’re looking for a new software to streamline a nagging process. You reach out to the industry leaders, expecting high end service, only to find delays, unfulfilled promises, and...

A professional's hands typing on a laptop that displays a holographic CRM interface with connected data points and management icons. This image symbolizes the transformative use of CRM software as a dynamic sales tool beyond just management.

Unlocking the Full Potential of the CRM

CRM: More Than Just a Management Tool Yeah, I get it. Most of you think the CRM is a waste of time. Most of you think the CRM just slows you down and that it’s a pain in the ass. You see it as something...

A 3D illustration depicts a figure pushing a large red percentage symbol uphill, against a backdrop of stylized mountains and trees, symbolizing the challenging journey to increase win rates in sales. The symbol's daunting size compared to the figure highlights the struggle organizations face with low win rates due to insufficient buyer input data.

Increasing Win Rates: The Critical Role of Buyer Data

Win rates are one sales metric that may stand alone as the single most important KPI. However, a staggering number of organizations struggle with alarmingly low win rates. Like 15-20%, low. These disappointing...

Two salespeople having a chat about why it's crucial to never stop learning in sales. They highlight the shift from old-school sales to a more helpful approach. This image represents the importance of always improving and staying adaptable for success in sales.

Gap Sell Keenan 71: Never Stop Learning

  We live in a constantly evolving world. Self development, professional development, and learning is a never-ending journey without a final chapter. The ability to adapt is non-negotiable. Sales has gone...

Two sellers engaged in a discussion, emphasizing the significance of knowing the answer to 'What problems do you solve for your clients?' in strategic sales.

Gap Sell Keenan 70: What Problems Do You Solve?

We’ve done 70 episodes of Gap Sell Keenan and there remains a recurring theme. Sellers still struggle to answer what problems do you solve? This seemingly simple question stumps our guests time and time again....

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