The Struggles (and how to overcome them) of Founder-Led Sales

How to overcome struggles of founder led Sales

Some wise words from Matt Wolach, B2B SaaS Sales Coach at Xsellus. While the focus of this podcast is founder-led sales, most of these principles that Matt shared can be applied to sales in general. Before you can grow in sales, you need to have a process and understand your market.

Spend time doing your research and talking to industry experts first, before you try to sell to prospects.

The other piece to founder-led sales…. don’t get emotional. Disconnect your ego from the product. Listen to the full episode to get even more great advice.

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Read the Podkast Transcript

Greg Reffner 0:00
One. Alright, everybody, this is Greg Reffner on the Abstrakt Podkast. We are joined today with Matt Wolach, SaaS coach and host of the SaaS Story in the Making podcast. Super excited to chat with Matt. Today, our topic, topic is going to be founder led sales, which is very relevant to me as a founder still leading the sales team here at abstract. And I’m hoping to pick up some words of wisdom from you, Matt. So please say hi.

Matt Wolach 0:31
Hey, how you doing? I hope I have some words of wisdom to share today, but I’m excited for the chat. Yeah, it’s

Greg Reffner 0:37
gonna be awesome. So before we kind of dive into the nitty gritty, Matt, of kind of the topic, let’s get into your background a little bit and how you kind of got here. So web PT is a pretty well known success story here in Phoenix, kind of the SAS world is kind of one of the ones to kind of emulate. And so I know you spent some time there. But how did you kind of get through your career to the point where now you are coaching, sales teams, founders, and how to deliver software, sales and repeatable revenue?

Matt Wolach 1:11
Yeah, yeah. Great question. So what PT was a fun ride. And one of the neat things about that was it was kind of at the beginning of the SAS revolution, right when SAS companies were kind of starting and becoming popular. And in our space, we were the only one we were the first one to be a SaaS product, there were 29 other systems. And they were all kind of a downloaded disk or something on on your own share driver on your own server. It was nasty. So our first challenge there was, how do we overcome that fear of SAS, and it’s in the cloud and educate our market on that. So that was a whole fun thing. But we did it, we had a fun ride at a lot of great times there. And, you know, I’ve had a couple other experiences since then, within the SAS world, so I kind of became a SAS guy and knowledgeable about all things SAS inside and out and, and especially around growing and scaling SAS companies. And along the way, as as we were seeing some success, and I was fortunate enough to have a couple exits, that worked pretty well. And I had people coming to me and saying, Hey, how did that how did you do that? What did you do? And can you explain it to us? And can you kind of walk my team through that? I said, Yeah, sure. So I would share a certain tactic or a formula that we had that we found that worked and let my friends they would apply it and they would see success.

Matt Wolach 2:26
They say, Wow, this is this is pretty cool. And so I realized, Hey, this is something that I could just do full time, just help people and make sure that they understood how they could scale and get better. And it’s been a lot of fun. I coach people around the world, that’s something that’s very passionate for me. And 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 of that 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.

Greg Reffner 3:00
That’s awesome. That’s awesome. So I want to touch on that real quick, where you said about kind of the fear of going from like download, install, download or install to like, through the cloud, that’s something I never would have even thought of like is something that you had to overcome as an objection. That’s crazy. What was the kind of give me the Cliff’s Notes version of how you guys helped, like owners of PT clinics overcome that in their mind?

Matt Wolach 3:28
Yeah, so it was kind of crazy, because we really had to sales efforts. First, we had to sell them on that product, or that type of product that SAS is the way to go. And we had to kind of counter sell against a downloaded version. And we had to let them know, if you download it, well, you’re not going to get free updates. And if something happens to your computer, it’s gone. Or if somebody steals your computer, it’s a security risk. So we had to kind of explain because they were so scared that all my information is gonna get stolen. And especially since we’re talking in the medical world, they’re worried about some of their healthcare security.

Matt Wolach 4:01
Exactly. And we had to say, hey, it’s actually more secure to have it with us than it is on your own servers on your own computers, your laptops that could just walk away. And and, and so that was our first sales effort, just kind of convincing them of the technology. And the second one is Ken, now you need to use our product. And so it really was a difficult thing. But we kept pushing through and really a lot of education. We brought in a lot of outside articles and explainers to show that we were not just making this up. And eventually, it helped it. It worked and people started to see the light, and we became the number one product within three years. That’s awesome.

Greg Reffner 4:39
I think we’ll touch on one of those aspects here a little bit later. But let’s kind of get a little bit more specific with who you’ve chosen to focus on that. So it looks like and based on our earlier conversation, you’re kind of going after companies that are maybe less than 1 million in ARR and trying to cross that chasm into a a repeatable sales motion. Why have you chosen to focus your time there? And kind of that kind of segment or cohort of companies?

Matt Wolach 5:11
Good question. A lot of reasons, Greg, first of all, that’s some of my most fun. In my past experiences, were in that early building phase, taking an idea, getting a team together to make this thing happen to make it a real product, and then explaining to others that this is something that can help them this is something we can solve their problems. I always enjoy that. 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.

Matt Wolach 5:45
That’s like, I mean, that’s gold right there, you’re just like, holy cow, that’s unbelievable. somebody sees value in something we put together here. Yeah, and especially when you get your first customer to get your first dollar in the door, it’s just unbelievable. So I love that whole energy from from those first early days plus, it is a lot harder. And I’m not the first one to say this, it’s a lot harder to go from zero to one than it is from like one to 1000. So that initial stage is so critical. And I’ve seen so many people who don’t put in the right formula, the right processes, and they fail, even if they have a great product, they didn’t know how to get from zero to one. And so they just absolutely fail. It’s oftentimes around marketing and sales, and they just can’t figure out a way to get to market, they can’t figure out a way to convince people to actually buy the product. That’s difficult. It’s frustrating. And so I wanted to help people, and I found a market that they needed to help. And it’s been amazing. We have a lot of interest in our services. And we’ve been fortunate to help a lot of people.

Greg Reffner 6:46
That’s awesome. So company, I was at all bound about five and a half years ago, it was a founder led sales team. And when I got in on kind of day one, kind of one of my, my objective objectives was to be able to tell the founder at the time, like, why aren’t you being successful at at this current sales motion. And I instantly realized that there was too much of a relationship, right, he was holding on to the connection between like, the outcome of a sale versus kind of the impact on the emotional aspect, like, Oh, if they don’t buy our product, it is a direct reflection on me as a founder and my idea. And then within a couple of weeks identified that there was there was kind of being there was too much being held on emotionally to the product, and then the outcome. And that was a fascinating experience to go through and kind of and kind of watch, do you. I’m jumping around a little bit, but I want to get into this topic. Do you often find that that’s the case and kind of the earlier days where there’s years or months put into this product? Now you have so much relied on getting that first dollar? And it’s it’s it’s not easy to disconnect the outcome from the impact on your ego or your emotions?

Matt Wolach 8:12
For sure. Yeah, absolutely. I felt that myself. I mean, like we said, you’ve put so much effort into this, and you’ve put your blood sweat and tears and you’ve done everything you can to make it amazing for somebody. And when you talk to that somebody, somebody in your target market who you think is a good fit, and you don’t get a good response. And for some reason they don’t buy you take it personally, I’ve taken it personally like what is Did I do something wrong?

Matt Wolach 8:33
Did I did I miss the mark somehow? And that’s absolutely. The life of a founder. I’ve often said to founders life is a roller coaster. One day, something great happens, you think you’re going to the moon, that thing is going to be amazing, we’re gonna IPO it’s gonna be unreal. The second day, you’re like, I need to update my resume, like, this is horrible. What are we doing here? And that’s absolutely the case and somebody doesn’t buy when you think they will you you feel bad about it. But one thing I coach my clients on, because we know in the buying process, you need that buyer to feel emotion, you want them to be emotional. And that’s how they make decisions. That’s how they take action is that they have enough emotion, usually a negative emotion about their current situation and positive emotions about what they’re trying to do. But if they have that emotion, then they’ll make the decision. But it’s difficult because you need to show passion, you need to show enthusiasm need to kind of get them going. But you also have to stay even keeled yourself. So while we want the prospects emotional, we need to stay flatlined. 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 it 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 this happens by the way, Greg, a prospect will be feeling that emotion and they’ll say this is great. This is awesome. I love it. And so as a seller, I deal with a lot of my founders on this. They get so excited that they actually stop doing some of the things they should be doing. Because they think, Oh, he’s gonna buy, I don’t need to finish out happy or this other stuff and they, so they don’t do some specific sales motions that you got to do to make sure things happen. Because even if people like it, you need to get over their own self of maybe losing priority on it or losing focus. So you need to continue to sell the rest of the process. So many times we get too excited, like, Oh, they’re gonna buy and then sir, two or three months goes by and you haven’t heard from them and you’re like what’s going on? They were so excited. So don’t get too high, don’t get too low stay even keeled emotionally while you get them completely ratchet it up. And it’s if you do that, then you are going to be amazing at selling.

Greg Reffner 10:40
So yeah, the happy years thing I struggled with that for the first couple of years, like, you know, all they said they like it, which means like, translated to, I’m gonna send them a contract, and they’re gonna sign today. Like, just because somebody likes something doesn’t mean they’re gonna buy something. So how do you go about coaching your clients to disconnect, like the sale? From being a personal attack on them on their idea? And maintain that kind of even level of emotion? Because that’s, that’s easier said and done, Matt? Like, I gotta say, like, so what’s maybe some some action items or listeners who maybe are founder leading sales teams can do to kind of help disconnect that?

Matt Wolach 11:24
Yeah, so one of the things we talked about is repetition. So first of all, if it happens to you, once you’re like, Well, maybe we’ve completely missed the mark. But if you have 10 calls, and it’s just one of the 10, that that happens, you’re going to feel a lot better. So continue to drive pipeline, continue to fill the pipe with perfect fit ideal candidates that you’re really wanting to help. If that’s the case, if they are the right fit, it’s not going to happen as often. Secondly, make sure that you’re only selling to those right fits if somebody is not a good fit. Don’t force it. And I ask people a lot I have people come to me and say hey, well, we did this demo for this guy. I’m like, Whoa, go back. Did you do discovery? Did you learn about them? Yes. Did you realize that they were a bad fit in discovery? Yes, I kind of saw that they wouldn’t be good. Did you still show the product? Well, yes. Why? If they’re not a good fit, don’t sell it to him. Like say, it’s not a fit. I’m sorry, we’re not going to help you. And by the way, and it’s super hard. I know how hard it is. And I came from the customer service side, like I was educated in Hospitality Management. That’s my degree. And so I live the life of the customer’s always right, and do whatever they say. It’s a total change in sales. You don’t do that don’t do what the customer says. It’s what you say. And so I would just do it just because I didn’t want to create, you know, any friction, and conflict. And so I’ll just be like, well, they want to see a demo and show it to him. And it’s not good. You’ve got to be able to Rick, recognize this is not a fit, and let them know, let them off the hook.

Matt Wolach 12:48
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 realized, 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. And so I’ve had business referred to me. And when I teach my clients this and they do that, then they’re like holy cow, he sent me another client. It’s unbelievable how it happens. So don’t get emotional, go through the repetition. And then the other thing is, I have a process called the perfect deal process. And it basically outlines 40 things that you need to do in your sales calls in order to get people super emotional to make sure they buy. And so the other thing is, let’s try and get more analytical on what happened. 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.

Matt Wolach 13:46
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, miss 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 a an analytical data backed type of thing, and it takes the emotion out of it.

Greg Reffner 14:08
So let’s talk about that for a second. I promised when we were prepping, Matt that I was going to likely go off on a tangent, and I’m going to deliver on my promise. So zero to a million in ARR means you maybe are scratching the surface of product market fit. Like you you don’t have product market fit yet at a million ARR least most of the investors I’ve talked to would would say that. So when you say like how, you know only sell to people within your ICP. How do you know who those people are when you’re trying to get your first dollar of revenue, your first $10 of revenue. Like that’s something we struggle with here and abstract is like who is that ICP and we’ve only been able to get that data after we’ve I kissed a lot of frogs. Right? So how do you strike that balance?

Matt Wolach 15:05
The founders I’ve talked to who have done it the best. Because I haven’t been amazing at it. I’ve I’ve been fairly lucky in certain times. And I’ve also done the trial and error thing of kissing a lot of frogs that didn’t work. And let’s Okay, let’s try that one. The founders I’ve talked to have done it the best. Those are the ones who have gone out and had 50 to 100 conversations with people in their market, who they think are going to be a fit, not sales conversations, more research type conversations, and just talking about 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, then really diving in and understanding who they are, that makes it so much easier to realize how you can develop the product towards that person, how you can align your marketing messaging to match with their lingo, and what they’re saying and what they’re trying to accomplish, how you can make sure your sales methods are going to be working for them.

Matt Wolach 15:55
And so much aligns once you really understand them, you can’t understand them until you really get to know them. So if you don’t come from that industry, so for me for, for example, I was a SAAS founder, and I talked to SAAS founders every day. So it made it a lot easier to know what that was. But for people who don’t come from that industry, it’s it’s really hard to kind of understand who they are, what are they trying to do? What would help them the most. And you really got to talk and have those conversations.

Greg Reffner 16:18
So it’s almost like, you know, maybe and would it be fair to say you don’t even treat it like maybe sales conversations, but more like market research conversations and kind of just doing some diligence on the market before you start going out and trying to sell.

Matt Wolach 16:33
Exactly, exactly that. And you know, what’s funny about that, Greg is, once you do that, you’re like, hey, I need some help. We’re trying to flesh out this idea. Just seeing if this is something that would work. Do you have 10 minutes. Once you do that, and just kind of run past them what you’re trying to do, they’re gonna be like, wait, wait, hold on. So I hope I helped. But tell me about this product, you’re gonna solve this problem. That sounds awesome. So it kind of works out. Even though you don’t, you’re not trying to. And so you actually will end up getting some some prospects out of it. But it’s amazing how beneficial it is, once you truly understand them. And the other thing is, once you do, 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.

Greg Reffner 17:26
I love that. I love that. Well, let’s get into kind of buttoning this up with one kind of final talking point. One of my favorite articles I’ve ever read was from Jason Lemkin, on Sastre, he talked about the 48 different types of VPs of sales. And the idea of myself hiring a VP of Sales one day, scares the shit out of me. Like, you know that I feel like that’d be one job that I micromanage. Like, I don’t know if I’ll be able to release the reins on that one. But for a lot of founders, they don’t come from a sales background. And so they’re very hesitant to hire this very expensive person that needs to kind of help them cross that next stage of the business. So how do you help coach founders through that kind of first sales hire, whether it’s a VP of sales are an individual contributor? What What kind of process do you take your clients through?

Matt Wolach 18:24
Well, I think it’s kind of what we talked about before, you have to put in a lot of people, like we said early in the show is they say, Well, let me I don’t really know sales very well. So let me just hire somebody to do it. And that’s the wrong way to go. I was just talking with another one of my clients who experienced this exact same thing this morning, we were chatting about this. You have if you bring somebody in before you have the process nailed before you fully understand everything that should happen within your sales motion, your sales process, you’re gonna be struggling so bad, and I’ve done this, I’ve hired somebody just because I’m like, Oh, he’s a great sales backer, let’s bring him in. Before I had everything flushed out. The guy sold nothing like nothing. He did it for months, nothing, no sales, even though I was selling, he had nothing. And it’s like, how can I sell and I’m gonna have your background and you come in, you can’t do it. Because they don’t have the methodology. You’ve got to be able to work that out yourself. You’ve got to be able to get the process in place and see success through the entire buyer journey, and then come in and bring somebody in so that they can run it and optimize it. Even if it’s a VP of sales.

Matt Wolach 19:32
Yes, I’ve seen people waste a lot of money on expensive hires directors VPs of sales, because they thought that they could come in and just make it happen. They don’t it doesn’t work that way. Get the process right. 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. And once you do that a few times and you’ve worked out the process that makes that work. Getting somebody in place is so much easier, because now they can follow the formula and And even better, as a founder, you know if they are doing it right or not, because you’ve done it, you’ve seen it. So you can tell if they start doing something like, actually, we try that it doesn’t work. We tried it multiple times, bunch different ways. It doesn’t work, it’s not gonna work. So you’re you’re wasting your time you’re wasting money. And it gets them so much more in line to say, follow this process, make sure the team follows the process. And the company will be so much better off that way. You’ve got an expensive hire. You’re right, who’s actually managing it? Well, because you’re right. A sales team can be very costly. But if it’s run well, and it’s a machine, it’s just become so incredible for your scale.

Greg Reffner 20:39
It gets exciting real fast, when when those wheels are turning, and they’re they’re well oiled. Yeah, yep. Well, kind of buttoning this up, Matt. Obviously, there’s a lot that we could have unpacked here. But we’ll kind of end with what it would be maybe your biggest takeaway, your biggest piece of advice for any founder, listening to our podcast today, who’s kind of, at that early stage, trying to disconnect ego from outcome, struggling with how to sell and what that repeatable process looks like? What’s the one piece of advice you’d give them?

Matt Wolach 21:12
The hardest thing in a founder is, you know, a lot of the founders are so great about I’m trying to soak up knowledge, I read this book, I saw all these articles, I went through this blog, I watched these videos. The problem is there’s a lot of different advice. And it all kind of stems from the same focus and around sales. But so what happens is you try this, and then it doesn’t work. And then you try that it doesn’t work, you start over, let’s go try this. And maybe that kind of works, but it’s not great. So you quit, you really have to follow kind of one methodology, follow one person or one ideology, and stick to it and make it happen. And so I have so many people come to me, they’re like, I read all this, I did this. And we’re still outstanding, like, stop that.

Matt Wolach 21:53
Like, let’s just get into the process, I’m going to show you exactly how to do each thing. And then once you see that there are real results, it allows you to be so much more confident. See some sometimes people get burned a couple times by a few things they try. And so the next one, they kind of just dip their toe in the water, and they don’t really give it a full effort. And you know, this Greg, running a business, dipping your toe in the water doesn’t really give you much, you’ve got to be fully confident, full speed ahead, let’s go let’s make this happen. And once you know that a process is going to work for you allow it allows you that confidence to be able to go full steam ahead and get things done. And that is the way you can grow your business. So I kind of went all over the place, but follow one methodology or one sales person, coach, mentor, whoever, and make sure that the team is aligned, and you’re hitting it hard and not just kind of let’s try this.

Greg Reffner 22:44
I love that. I love that, like go both feet in, right. You can’t like tippy toe around and expect to be successful in anything you do in your life, let alone trying to start a software company. So so

Matt Wolach 22:55
true. So true. I mean, perfect example. I know you want to close, but one of my clients rose yet he had tried all these different things. Nothing was working. He came in, I showed him. Here’s here’s why it’s not working. Let’s put this process in place. He did it. And in three weeks, he closed a $50,000 deal, his shortest sales cycle and his biggest clothes he’d ever had. So if you just stick to one process and hit it hard, it works. Yeah.

Greg Reffner 23:19
Yep. I love that. Man. I I think sales is something that scares a lot of people. And into my mind. It’s so it’s very process oriented. It can be once you kind of have it figured out like it is rinse and repeat. You ask the same questions, you send the same emails, you know what questions elicit which outcomes and emotions like that’s why I love sales so that anybody wants to get a hold of you and kind of learn more about your services and maybe look to work with you what’s the best way to get a hold of you?

Matt Wolach 23:49
Sure. I’m really active on LinkedIn. So you can go to Matt Wallach on LinkedIn. It’s matt Wolach. And also is the website and a lot of information there and also post a lot of tips. So if you go to tips dot Matt It has a ton of tips on growing your business, go to market channels, you can you can target ways to sell ways to close everything you can think of.

Greg Reffner 24:13
Love it. Well. Appreciate your time today. This has been awesome. Good. Some good reminders for me as kind of a founder led sales team, I guess here at abstract. And, again, thank you for your time and wisdom. We appreciate it.

Matt Wolach 24:27
My pleasure, Greg. had a lot of fun.

Greg Reffner 24:29
Cool. We’ll talk to you soon, Matt.

Matt Wolach 24:30
All right. Thanks. Take care. Bye. 

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