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Software Sales Tips by Matt Wolach

Sales Tips

Why the One-Pager Doesn’t Work

Many think that a software company’s one-pager is a valuable document. It allows you to present your company’s offer concisely and factually, which can help you attract potential customers. But what if I tell you that it doesn’t work? The goal is that the one-pager is going to convince the decision maker from your prospect’s […]

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Sales Tips

The Right Thing at the Right Time

Early in my SaaS career, when I was taking on sales leadership responsibilities for the first time, I often asked myself if I would have the courage to do the right thing the right way if (and when) challenged with difficult business decisions.  Sometimes, you have to make tough business decisions that are right and […]

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Sales Tips

The 3 Best Discovery Questions

When people think of discovery, they believe it’s just the getting-to-know stage of the sales process to see if the deal would work out or not. They imagine a ton of questions and answers where both parties check to see if the “relationship” is worth it.  But in reality, it’s so much more than just […]

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Sales Tips

How to Deliver a Great Demo

When you think of software demos, content is the most crucial of all the components. It’s akin to the hero of the story, the main star. But what if I told you that the delivery can actually save the day, go beyond, and turn your demo into an absolute legend? Like the moviegoers of a […]

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Sales Tips

The Three Must-Have Pieces of the Demo

How many demos have you given where the prospect ended up ghosting you?  Chances are, you were missing one of the vital ingredients to the formula for successful demos.  So here’s a little something for you that will help you start closing those demos at scale: – the three must-have pieces of the demo. By […]

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Sales Tips

3 Easy Ways to Prevent Churn Through Great Sales

They say that churn is normal in sales regardless of your product efficacy.  You could have the most fantastic product to have ever graced the planet, and customers would still leave it. Worse, they may even leave a negative review online or go out of their way to discourage potential buyers. While it’s true that […]

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Sales Tips

What to Fix First, Sales or Marketing?

When it comes to scaling a software business or launching a product, the gut instinct might be to fuel the pipeline. After all, how are you going to get leads without strong marketing? This is why most companies invest heavily in marketing whether they’re veterans or start-ups. They want more brand awareness as, intuitively, that […]

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Sales Tips

Never Train in Your Demos

  Here’s a fun fact: the vast majority of software demos fail to emotionally motivate a prospect to take action. This is due to a number of mistakes that are made in the demo process.  One of the biggest mistakes that I see a lot of which hurts your chances of closing deals is when […]

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Sales Tips

The Most Powerful Stories That Close Deals

Today, we will set the record straight on the most effective way to deliver a sales pitch. It’s through storytelling.  Storytelling builds an invaluable human connection between sales teams and prospects. So, to close more deals, you need to tell stories. However, not everyone knows how to execute this well. You may know in your […]

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Sales Tips

How Wine Is Like Sales

Winemaking has been around for thousands of years.  In its basic form, wine production is a natural process that requires very little human intervention. Mother Nature provides everything that is needed to make wine—it is up to humans to embellish, improve, or totally obliterate what nature has provided, to which anyone with extensive wine tasting […]

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Sales Tips

Flip the Risk

When selling software, your solution is among your prospects’ many options.  Knowing the risks of purchasing a tool, it is normal to seek several choices—at the end of the day, all they want is to solve their pains. But you are not going to be chosen by staying this way. Instead, what you need to […]

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Sales Tips

How Software Founders Can Scale and Travel the World

Some of the top reasons for wanting to start a software company are to achieve financial freedom and to travel the world.  To be able to take a week or a whole month off and splurge in a foreign place is the ultimate goal. But no matter how short or long the actual vacation is, […]

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Sales Tips

How Much Product Do Sales Reps Need to Know

When you are a growing SaaS company, you may want to make sure that you are building a team that knows the intricacies of your product so that they can sell it well. Gaining mastery of its purpose and its ups and downs feels like it allows them to highlight the product’s best features and […]

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Sales Tips

Stop Having Prospects Ghost You

The term ghosting comes from the dating scenes, but salespeople struggle with the same phenomena in business. I believe every SaaS founder and sales professional can resonate with the following story of their sales career. You had a great conversation going with one of your promising prospects. Exchanged emails, delivered your sales pitch, nailed your […]

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Sales Tips

How Sales Is Like Comedy

Recently, I was listening to a comedian talk about how they do what they do. And something amusing is that they said comedy is 10% what you say and 90% how you say it. It’s crazy because it’s the exact same thing in sales.  Yes, you want to say the right thing, but how you […]

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Sales Tips

How to Sell SaaS Without Selling

Sales, specifically selling your SaaS product, is essential in ensuring that your business will thrive.  Sell, or your company will fail, and you will go bankrupt.  We’ve all heard that sales and deal-making are the lifelines of any company. Without them, there is no exchange of money, and without money, you will not last long. […]

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Sales Tips

Turning Software as a Service Into Success

You may have heard about the term or read about it elsewhere, and many people have been asking what it is all about. SaaS may be a foreign term to many of us, but it has been essential to our everyday lives. Take Gmail as an example. You can just access it via your web […]

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Sales Tips

Good Is the Enemy of Great

I recently had a client who told me that their sales process and the demo were good. They were happy in the situation that they were in. However, being good is not entirely “good.” This suddenly reminded me of the book “Good to Great” by author Jim Collins. It is an excellent book about the […]

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Sales Tips

Great Marketing, Terrible Sales

Gone are the days when marketing and sales did not get along and it was fine. Understanding how one department can help the other allows them to work together efficiently. When done right, they can continuously attract and secure customers for the business. However, some SaaS companies fail to create balance among these areas–prioritizing one […]

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Sales Tips

Why Product Led Growth Doesn’t Work

In today’s business landscape, it sounds like an easy job to develop a product to the best it can be and let it do all the “selling.” This way, you are relying on the product’s performance and features rather than boosting your sales process.  It is a business strategy called Product-Led Growth, which puts the […]

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Sales Tips

Lessons Learned From a 1000-Piece Puzzle

Putting a 1000-piece puzzle together is a real challenge. There are no fixed steps to assemble it, and you can only progress and figure it all out as you go along.  My daughter and I spent a couple of weeks (almost) completing one. There were inevitable hurdles in this little journey, but it was fun, […]

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