Software Sales Tips by Matt Wolach

Scale Your SaaS

Top Sales Process Tips for New Founders


Every software CEO or founder struggles at the start of their company and makes mistakes. Getting too emotionally invested in the outcome of a sale, hiring an expensive executive to figure out your sales for you, or just generally missing some steps when closing deals. One thing is for sure, we’ve all faced that uphill battle of going from zero to one, so let me tell you how to win the war.

B2B SaaS Sales Coach Matt Wolach recently guested on The Abstrakt Podcast with its CEO and Founder Greg Reffner to share his insights about founders’ various struggles in sales. Matt also gladly shares several nuggets of wisdom in dealing with the issues, along with examples from his clients’ and own experience. Read on to find out how to close sales steadily and keep it cool!


Podcast: Abstrakt

Host: Greg Reffner, CEO & Founder at Abstrakt

Guest: Matt Wolach, a B2B SaaS sales coach, Entrepreneur, and Investor


Be Objective While Emotionally Moving Prospects

As software founders, we put our blood, sweat, and tears into our companies. It’s almost a no-brainer that we’ll get attached to it. But to keep on closing, we have to be well-balanced. Of course, we want the opposite for the buyers as emotions motivate them to take action. But it’s crucial that we remove our egos from the ongoing deal so that we don’t lose the will to try again if things go south.

Going analytical also helps in reigning the emotions down. What this means is, to look back at the recordings of your prospect calls. Yes, you have to record. See if they’re the right fit and if you’ve missed specific points. You’ll find that, while dissecting the experience, you naturally start to detach from it.

One might say that taking the emotions out of the sales process is easier said than done but it can be easier for you through repetition! Failing one out of ten times doesn’t sound as bad as failing one out of three times. Now, how do you get a high success rate? 

Understand the Leads Who Are the Right Fit

First, you should ensure you’re talking to the prospects who are the right fit for your product. If during discovery you realize that they’re not the right fit, politely let them know, and try to point them in the right direction. When you sell to the right person, you won’t have to struggle so much with closing or even retaining the customer. They’ll want to buy your stuff since it’s perfect for them.

To go one step further, you want to seal the deal by making them feel you truly get them. People naturally lean to those who are like them. You do this by having conversations with the prospects and asking questions like these:

  • What are the pains you’re struggling with?
  • What keeps you up at night?
  • What are you trying to accomplish?
  • What is your team working towards?

Once you have all those key information, you can tailor fit your products to them and use the right message when marketing. It means you start talking the way they do. A bonus of doing market research before a sales conversation is that you also get prospects that way. When they hear that your product fits them, they’ll be interested in knowing more. It helps that they were the ones who took the initiative and it’s not like you asked them to buy.

Now, what happens when they’re not the right fit?

Don’t Be Afraid To Say No

It’s a lot like a romantic relationship. You know how people say in some breakups that it wasn’t anybody’s fault? It’s the same in sales. Sometimes… it’s just a compatibility issue. And that’s okay, it just means that you have to find the right people for your product.

So now that we’ve established that, we go to the dreaded next step. Say no. Seriously. It doesn’t have to be a bad experience if done right. You kindly and objectively tell them that the information you received from them shows they are not the right fit. Then you suggest products from other people that you think are the best fit for them.

See, this really works because you gain their trust that you’re not just out for the money. They also feel genuinely listened to, and anyone from customer service can attest that customers want that the most. Out of gratitude, they may suggest others to you who might be a fit so it’s yet another lead generator. Another silver lining is that you end up building rapport with the founder of the company you recommended them to.

Always Complete the Sales Process

One consequence of emotional attachment in a deal is that when customers act like they’re over the moon with your product, you might start to expect that they will buy. Then, months go by, and you haven’t heard back from them. You might wonder, just what went wrong? It may have been that you stopped making further sales motions.

Even if a prospect seems to really love your product, nothing is certain. They can always change their mind or find something they think is better. A company with better marketing can woo them away. To put it into perspective, it’s a lot like how you shouldn’t expect marriage from someone after you just met them in a bar. You have to take all the necessary steps to get that ring on your finger so to speak.

Establish the Methodology Before Hiring a VP of Sales

It may seem counterintuitive to figure out your own sales process before you hire a VP of sales. You might even go, ‘Isn’t that the job I hired them for?’ But the thing is, if you don’t have the right formula, they will likely trial-and-error their way to it. And there would be way more errors, meaning wasted money, than solutions.

It’s also better for you to figure it out yourself to truly know your company inside and out up to every capillary. That way, you know you’re going to succeed without your staff, and while with your staff, things are just going to be considerably better. See your VP of Sales as a booster to an already complete and powerful engine.

So how do you begin to figure out the process if you have no prior background in sales? It’s simple, you understand your customer. Make sure you are solving their needs. Make sure they understand that you are solving their need, make sure they understand how bad their situation is, and get them closed.

Stick to One Process & Hit it Hard

One rabbit hole that a lot of enthusiastic and driven founders fall into is that they consume way too much information. There isn’t anything wrong with learning as much as you can but what actually happens is that they try all the different advice that they’ve heard. Think of it as taking different prescriptions for the same disease. The meds will go against each other, and you’d likely overdose.

The key here is to find one person or methodology to follow. This way, you won’t get so burned after trying various processes to the point that you only dip your toe in the next one. Business is demanding and walking on eggshells is not going to cut it. So take your time in finding that and, once you do, commit to it.


The Life of a Founder Is a Rollercoaster Ride

As a founder, there are days when you feel like you’re on top of the world, and getting into the Fortune 500 is within your grasp. Then come the days when you’re rethinking your entire life and wondering if you should jump off a sinking ship. Then you get into sales, and man does that rollercoaster become huge. But even if it’s scary as hell, it’s worth it when you finally make it. And when you look back, you’ll see how much fun it really was.

The Customer Is Not Always Right in Sales

We all have heard the famous business adage, “the customer is always right,” but that couldn’t be farther from the truth in sales. One example is when they buy your product even if it isn’t the right fit. It may seem like it’s not a big deal but what will happen is that they’re not going to have a good experience and they’ll talk about that. That’s going to be bad for lead generation. So do what you say and not the customers. Be the one behind the steering wheel. 

Liking Products Does Not Equate To a Sale

Sadly, it’s just like in the dating ring. Even if someone is attracted to you, it doesn’t mean they’ll enter into a relationship with you. Due to a variety of reasons, a customer may not buy your product. An example is when they’re not yet financially ready to do so, and that’s perfectly fine. So keep this in mind when hearing prospects rave about your products and, as was mentioned before, stay grounded.


Matt Wolach

[2:51] “I want to make sure that I am giving back and helping others. And when I have somebody who comes to me struggling, they say, ‘Hey, we’re having a tough time growing, we can’t figure this out.’ And I can give them a process that they plug and play. And now they can see the success. That’s everything I live for. That’s just so amazing for me.” 

[5:45] “And when you first have that first conversation with a prospect on something you’ve worked so hard on for months, and you explain it, and they say, ‘Wow, this is great.’ That’s like, I mean, that’s gold right there. You’re just like ‘Holy cow, it’s unbelievable. Somebody sees value in something we put together here.’ And especially when you get your first customer, you get your first dollar in the door, it’s just unbelievable. So I love that whole energy from those first early days.”

[9:40] “And we need to realize, don’t get down if something goes wrong. Don’t get down if you say something kind of a little off and it wasn’t exactly how you want to say it or didn’t show the product right or you didn’t do this. Don’t worry, they probably didn’t know. But also, conversely, don’t get too high on emotion if they say ‘Oh, I love this. I love this,’ too many times.”

[12:53] “You’ve got to be able to really recognize this is not a fit, and let them know. Let them off the hook. ‘So you know what, based on what you’re telling me, I don’t think this is the right system for you. In fact, let me see if I can recommend other systems that might be a better fit for what you’re doing.’ And guess what? They will love you. I’ve had people refer business to me after I told him ‘no, we won’t help you.’ Because they realize this person is not just trying to sell something, they’re not trying to. They’re actually trying to help real people. And maybe I’m not a fit, but my friend might be.”

[13:45] “If you say, ‘It didn’t go bad. I’m horrible. People hate me.’ That’s not a good cycle. Instead say, ‘Well, what went wrong? Let me go back, get back and analyze. Let me look at the recording.’ You should be recording all your calls by the way. ‘Let me go look at the recording. And let me see, did I do this as part of the process? No, I missed that. Did I do that? I got that. But I missed this. I missed this, missed this.’ And you can see ‘oh, so maybe that’s why it didn’t work out. He was the right fit. But I missed all of these things that I was supposed to do. And that’s why it didn’t happen.’ So it’s much more of an analytical data-backed type of thing, and it takes the emotion out of it.”

[17:08] “It’s amazing how beneficial it is once you truly understand them… you’ll start speaking the way they speak, you’ll start thinking about the same things. And then they will realize in conversations that you get them. If you have a prospect who says this person is like me, they totally get me. They will love you and they will want to buy everything you can sell because people want to buy from people who are like them and who understand them. And that level of trust will skyrocket.”


For more about how host Matt Wolach helps software companies achieve maximum growth, visit