Why Gap Selling is Essential for Modern Software Sales Success

Gap selling changed the game for me in selling software, turning challenges into big wins.

Let’s explore some basics and easy, practical tips to help you boost your sales with this awesome approach.

Why are sales tough?

Sales can be a tough game, even for the pros. The market is always changing, with new competitors and shifting customer expectations (and AI, of course). Figuring out why sales are challenging is the first step to getting better at it.

One big reason sales are hard is because people are unpredictable. Buyers don’t always act rationally; their decisions can be swayed by emotions, personal biases, and outside pressures. This means that even a perfect pitch can miss the mark if it doesn’t connect on a personal level.

Plus, digital technology has changed the sales landscape a lot. Buyers have tons of information at their fingertips, making them more informed and sometimes more skeptical (so you need more than 5 follow-ups to make a sale). They often do a lot of research before even talking to a salesperson, so you must offer value beyond what they already know.

Another challenge is the sheer amount of noise out there (as a result - increased sales cycle). With so many brands fighting for attention, it’s tough to get your message heard. You need a strategy focusing on building relationships and trust, not just pushing your product.

And, of course, there’s the pressure to meet sales targets, which can lead to stress and burnout (because 21% of salespeople reach their goals). Constantly chasing quotas can create a high-pressure environment that’s tough to handle if not managed well.

That’s why resilience and the ability to bounce back from rejection are so important in sales.

What are the sales techniques to “relieve the pain”?

Today, I’m a content guy. But when I first jumped into sales, I quickly saw how tough it could be. The constant pressure to hit targets, unpredictable buyers, and the ever-changing market were pretty overwhelming.

But over time, I found some techniques that made the whole process a lot more manageable and even enjoyable. Here are a few that worked for me:

1. Build relationships, not just deals

   One of the biggest lessons I learned was the importance of building genuine relationships with clients.

   Early on, I was all about closing deals, but I soon realized that connecting with my clients on a personal level made a huge difference. By really listening to their needs and concerns, I could offer solutions that truly helped them, which made them more likely to trust and buy from me.

   
   

2. Embrace continuous learning

   Sales techniques and market trends are always changing. To stay ahead, I committed to continuous learning. I read books about sales, attended seminars, and followed industry leaders. This kept my skills sharp and gave me fresh ideas to improve my sales strategy. Staying updated with the latest trends helped me anticipate my clients' needs and position myself as a knowledgeable resource.

   
   

3. Leverage technology

   At first, I was hesitant about relying too much on technology, fearing it might replace the personal touch. But, I soon realized that the right tools could actually boost my efficiency and effectiveness.

   
   

   HubSpot, for instance, helped me keep track of client interactions, ensuring no lead slipped through the cracks. Some sales engagement tools like Reply handled repetitive tasks, freeing up more time for building relationships and closing deals.

   
   

Here are some of the Top sales tools in 2024, according to G2:

4. Stay resilient and positive

   Sales are full of highs and lows. Rejections can be tough, but I learned to see them as opportunities for growth.

   Every "no" brought me closer to a "yes."

   Maintaining a positive attitude was crucial. I started celebrating small wins and learned to bounce back quickly from setbacks. This resilience kept me motivated and energized.

   
   

5. Focus on value, not price

   Early in my career, I often got stuck in price negotiations.

   I discovered that shifting the conversation to the value my product or service could bring made a significant difference.

   By clearly explaining the benefits and addressing my clients' specific pain points, I could justify the price and show why it was worth the investment.

   
   

These techniques have been key in making sales easier for me. But gap selling has completely changed the game, taking things to a whole new level.

What is gap selling?

What I know about it, is that “gap selling” is a technique that’s all about finding and filling the "gap" between where a client is now and where they want to be.

The goal → uncover their problems and challenges and show how your product or service can solve them and help them reach their goals.

From my experience of 10 years in sales, gap selling involves asking smart questions (I’ll show you mine a bit later) to get a clear picture of the client's current situation, their desired future, and what's stopping them from getting there. This helps you show the real value of your solution and why it’s the perfect fit for their needs.

In practice, this means shifting from just selling a product to actually solving a problem. It makes your pitch more compelling and relevant. It’s all about delivering real value and demonstrating how you can help the client bridge their gap.

How can you start using gap selling?

Getting started with gap selling is pretty straightforward, as for me. Here are some practical steps to help you bring this approach into your sales strategy:

1. Understand your clients’ current situation

Start by asking detailed questions to understand where your clients are right now.

For example, if you’re selling software, find out what tools they’re currently using and what challenges they’re facing.

2. Identify their goals

Next, uncover what your clients want to achieve.

Ask questions that help them spell out their goals and aspirations. For instance, if you're in real estate, ask what their ideal property looks like and why it matters to them.

3. Discover the gaps

Find out what's stopping clients from reaching their goals.

For example, if a client wants to boost productivity but is stuck with outdated tools, that’s a gap your product (or a service) can fill.

4. Tailor your pitch

Show how your product or service can bridge these gaps.

Use examples and case studies to back up your points. For instance, if you’re selling marketing services, share how you’ve helped other clients overcome similar hurdles.

5. Leverage technology

Use tools like Reply for personalized outreach, HubSpot for organizing client information, and Lavender for crafting clear, engaging communication.

Some of our day-to-day sales activities can be (and must be) automated.

6. Measure and adjust

Keep track of your results with metrics like conversion rates and customer satisfaction.

Regularly review these numbers and tweak your approach as needed.

How did I start using gap selling?

When I first used gap selling to pitch a product—let’s call it just a sales engagement tool (to keep the articles less salesy)—I targeted a mid-sized tech company that was struggling with its sales outreach. Here’s a practical breakdown of how I applied gap selling to close the deal:

Understand the current situation

I started by having a candid conversation about their current sales process:

• What tools are you using for sales engagement right now?
• What problems are you running into with these tools?
• What features do you wish your current tools had?
• How do you track and manage your leads?
• How do you currently handle follow-ups with potential clients?
• How important is automation in your sales process?
• What budget do you have allocated for improving your sales tools?

They admitted they were juggling multiple disconnected tools, leading to inefficiencies and lost leads.

Identify their goals

Next, I dug into what they wanted to achieve:

• What changes would make a big difference in your sales engagement?
• What are your top priorities for improving your sales process?
• How do you define success in your sales engagements?
• What are the KPIs (OKRs?) you focus on?
• What would an ideal sales engagement process look like for you?
• What are the biggest bottlenecks you currently face in reaching your sales targets?

They dreamed of an integrated solution that could streamline their sales outreach, improve lead follow-up, and boost the closing rate (don’t know a company that doesn’t want it!).

Discover the gaps

Through our chat, I uncovered the gaps:

• Disconnected tools causing chaos
• Poor tracking of lead interactions
• Ineffective follow-up resulting in lost opportunities

These gaps were seriously hurting their sales performance.

Tailor the pitch

Here’s where the magic happened. I tailored my pitch to address these specific gaps:

• I explained how the product integrates various sales tools into one cohesive platform.
• I demonstrated my product’s advanced tracking features for better lead management.
• I highlighted automated follow-up sequences to ensure no lead falls through the cracks.
• I showed off the AI tools that personalize and optimize cold email outreach, increasing engagement rates.

To make it even more relatable, I shared a case study of a similar company that saw a 27% increase in conversion rates after using my product.

Why did I start using gap selling?

When you start using gap selling, you can expect some pretty impressive results. Here are a few practical outcomes and how to measure them effectively:

Increased conversion rates

One of the first things you’ll notice is a bump in your conversion rates.

Focusing on your client's specific needs and showing how you can solve their problems makes your pitch much more compelling. To measure this, track your lead-to-customer ratio using tools like HubSpot’s CRM (I love their product).

For example, I worked with a software company that saw their conversion rates from first contact jump by 27+% after switching to gap selling.

Shorter sales cycles

Gap selling can also shorten your sales cycle. When you directly address the client's pain points, they’re more likely to move quickly through the decision-making process.

A colleague in the B2B sector managed to reduce their average sales cycle by 30% by clearly identifying and addressing gaps in their prospects' current processes. Measure this by tracking the time from initial contact to closing the deal using your CRM.

Higher customer satisfaction

When you solve real problems for your clients, they’re happier with your service.

This leads to higher customer satisfaction and more referrals. I’ve seen businesses improve their NPS significantly after adopting gap selling.

Use tools like SurveyMonkey or HubSpot's customer feedback (yeap, another HubSpot here and no affiliate links) features to regularly survey your clients and track satisfaction scores.

Better client retention

Happy clients are more likely to stick around. By continuously addressing their evolving needs, you can improve client retention rates.

For example, a SaaS company I know increased its retention rate by 20% within a year by focusing on gap selling. Measure retention by tracking the percentage of clients who renew their contracts or continue purchasing your services.

To measure these results effectively, set clear benchmarks before you start. Use your CRM to track metrics like conversion rates, sales cycle length, customer satisfaction scores, and retention rates.

Regularly review these metrics to see how gap selling is impacting your sales performance. Adjust your approach as needed to keep improving.

And, goddamn, give gap selling a try, and watch your sales skyrocket!