Software Sales Tips by Matt Wolach

Scale Your SaaS

Stop Blaming the Macro-Economic Situation on Poor Revenue – with Matt Wolach

https://surfandsales.libsyn.com/s5e23-matt-wolach-stop-blaming-the-macro-economic-situation-on-poor-revenue

EPISODE SUMMARY

Building an effective and dynamic software sales team is crucial in the competitive sales world. Software sales industry leader Matt Wolach joins Scott Leese and Richard Harris in the Surf and Sales Podcast to share his insights on various aspects of sales team dynamics, strategies for success, and the evolving SaaS sales landscape. Read more to learn valuable takeaways for software sales founders and leaders.

PODCAST-AT-A-GLANCE

Podcast: Surf and Sales Podcast by Richard Harris and Scott Leese

Episode: Season 5, Episode No. 23 – Matt Wolach – Stop Blaming the Macro-Economic Situation on Poor Revenue

Guest: Matt Wolach, a B2B SaaS Sales Coach, Entrepreneur, and Investor

Host: Richard Harris and Scott Leese

TOP TIPS FROM THIS EPISODE

The Dynamics of Building a Software Sales Team

Hiring the Best People

One key point emphasized is the importance of finding the best people for a software sales team, regardless of background or appearance. Embracing an inclusive approach ensures the team is diverse and brings varied perspectives. This diversity can be a significant asset, fostering creativity and innovative problem-solving within the team.

Adapting to Market Needs

A critical aspect of building a successful sales team is aligning sales strategies with market needs. It’s essential to be flexible and responsive to market conditions. For example, if cold calling proves to be effective in a particular market, the team should leverage this strategy. Conversely, adapting and exploring other methods is crucial if the market dynamics change. This flexibility ensures that the team can achieve optimal results regardless of the market conditions.

 

Understanding Market Dynamics

The Importance of Conversations

Engaging in conversations with potential ideal-fit prospects before initiating sales is vital. These conversations help understand what prospects care about and guide the go-to-market motion. By having at least fifty conversations minimum before starting the software sales process, teams can gather valuable insights that inform their strategies and improve their chances of success.

 

Consistency and Persistence

Another critical factor is gathering statistically significant data before changing software sales strategies. SaaS sales teams can base their decisions on reliable data rather than premature conclusions by making over a thousand calls and having around a hundred conversations. This approach ensures that adjustments to sales strategies are informed by substantial evidence, not just gut feelings or anecdotal experiences.

 

Key Traits in Salespeople

The Desire to Help

A common trait among successful software salespeople is a genuine desire to help their clients. The best sellers focus on solving problems and assisting clients to achieve their goals. This trait, combined with confidence in the product, drives successful sales. When salespeople believe in the value of their product and its benefits for the client, they can effectively convey this confidence, making them more persuasive and credible.

Balancing Help and Drive

Balancing the desire to help with the drive to close deals is crucial. Software salespeople must be empathetic and focused on the client’s needs while also being effective closers. Confidence in the product is essential; if salespeople do not believe in what they are selling, convincing others of its value becomes challenging. A balanced approach ensures that salespeople can build strong relationships with clients while achieving their sales targets.

 

EPISODE HIGHLIGHTS

The Shift to Remote Work

Challenges of Remote Software Sales

Starting a SaaS sales career remotely presents unique challenges. The lack of immersive, in-person experiences makes it harder for new salespeople to learn and grow through osmosis. Being physically present in a sales environment allows for more effortless knowledge transfer and mentorship, which are crucial for developing latest sales talent.

Maintaining Team Dynamics

Maintaining team energy and dynamics in a remote setting is essential for sustaining morale and productivity. The energy of a team when they are all together can be a powerful motivator. Celebrating successes and coming together during challenging times are essential aspects of team dynamics that can be harder to replicate in a remote setting. Finding ways to foster this sense of team unity and shared purpose is critical for remote sales teams.

 

Leadership and Management Challenges

The Need for Leadership Training

Leadership training is crucial, especially in a remote work environment. Effective leadership involves managing tasks, managing people, and fostering their development. Unfortunately, many SaaS sales leaders lack training in these essential soft skills. Investing in leadership development programs can help address this gap and equip leaders with the skills to manage their teams effectively.

Adjusting Sales Strategies

Adjusting sales strategies based on real-world data is essential. SaaS sales cycles may have adjusted, necessitating changes in revenue targets and forecasting. Sales teams can set realistic and achievable goals by building revenue targets around longer sales cycles and using accurate data to inform these adjustments. This approach ensures the team is aligned with the actual market conditions and can plan accordingly.

Conclusion

Building and managing an effective software sales team requires understanding market dynamics, adaptability, and fostering a culture of help and support. Leaders must equip themselves with the skills to manage remote teams and adjust strategies based on real-world data. Consistency, persistence and a genuine desire to help clients are vital traits that drive success in sales. As the sales landscape evolves, staying informed and adaptable is crucial for long-term success.

 

TOP QUOTES

Matt Wolach

[13:08] “I always like to say that if cold calling works, then do it. If it’s email outreach, then do that. Whatever is best for your market, you need to go in that direction.”

[14:50] “It’s crucial to have conversations with ideal-fit prospects before you actually get into selling, so you know what they care about and what the go-to-market motion should be.”

[15:20] “I tell my clients to have at least fifty conversations before they start selling to understand their market.”

LEARN MORE

For more about how Matt Wolach helps software companies achieve maximum growth, visit https://mattwolach.com.

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Check out the whole episode transcript here:

Richard Harris  00:02

Greetings and salutations, everybody. It is Richard Harris for the Surf and Sales podcast, here with my co-founder, Mr. Scott Leese, who just came up with the best quote ever. Scott, how are you doing? And then maybe you should tell people about this fantastic quote. 

 

Scott Leese  00:20

I’m hanging in there, man. I’m a little bit a little bit stressed right now scrambling for my overseas adventure. 

 

Richard Harris  00:27

Where are you headed? Are you going to Spain? 

 

Scott Leese  00:29

Well it’s more than Spain. But yes, going to Spain, Gibraltar Morocco.

 

Richard Harris  00:35

You’ve never traveled with me. I’m so disappointed. 

 

Scott Leese  00:39

I guess seven eight years of Costa Rica trips doesn’t count. I guess. 

 

Richard Harris  00:44

That’s business. Yeah.  

 

Scott Leese  00:47

You want to hear the quote? I already forgot. I already forgot the quote is something something to the effect of, I’m a hard maybe millionaire. Or I’m a millionaire off of hard maybe that’s like, it’s like the verbal board. It’s like saying, not this year. But next year for sure. Right? Right. can’t sign this month. But next month, hit me up, Richard. Yeah, we’re all we’re all hard Maybe millionaires 

 

Richard Harris  01:13

Absolutely. Love it. So let’s get to the important stuff. And because people don’t listen to hear us want to introduce our good friend, Matt Wolach, who is a SaaS investor, founder, innovator, just sales coach, leadership coach, all those kinds of coaching. I assume there’s some life coaching in there too, Matt. So Matt, how are you? Feel free to introduce yourself, name your company, what you’re focusing on these days just so people have a context of who you are? 

 

Matt Wolach  01:44

Sure thing. Yeah, Richard. I’m super good. Thanks for having me, Richard. And Scott, this is awesome. I am really jealous about not being able to go to Costa Rica in November with you guys. Sounds amazing. And the amazing quote Scott came up with came because I gave him a hard maybe for next year. So that’s, that’s on me. Totally. I would hate hearing that myself. So

 

Richard Harris  02:06

he outed himself, which, in fairness, he gets he gets a 50% hall pass, at least for me, because he can’t come because he’s going to some Bronco home games. And as a big Bronco fan, that that’s helpful. And Scott, I’m gonna throw this at you. You missed you missed the fact that he went to school in upstate New York. So he has a lot of friends who are Bills fans. And I said that you’re like, uh, you live off the disappointing blood of like a vampire of Buffalo Bills suffering, right? Every every cut, every cut goes deep. And the only option you have is to just live off that, you know, blood that keeps coming out every week. Barely gross. But anyway, 

 

Matt Wolach  02:48

yeah, those poor Bills fans, we keep holding as Bronco fans, we keep hoping you beat the Chiefs for us? But hasn’t worked well at all. 

 

Richard Harris  02:55

no, not at all. So. But we’re not here to talk about football. We are here to talk about sales. We are here to talk to another. Yep. Although we could do it. We are here to talk about challenges people are having. So what are you seeing these days in the world? Like what is? What are people coming to you for it is June of 2024. Just so people have context. What are people struggling with? 

 

Matt Wolach  03:19

My big thing that people keep coming to me for is simply the bottom of funnel closing process. It seems like people have started to figure out in many cases, how can we generate leads? How can we generate some buzz create some interest? How can we get people at least to start to look at their pipeline.  

 

Richard Harris  03:35

is that is that bottom of the funnel? Or that sounds like talk on the funnel? 

 

Matt Wolach  03:38

No, I I’m focused on the bottom. Yeah, I mean, I’m focused on how do we get them over the line? How do we get them signed? So people are coming to me saying, Okay, we’ve got some leads. We’ve done a good job of generating some interest, but we’re having these conversations and they go nowhere. People say, hey, it’s, it seems like this is a good thing, or I like your product. I’m very focused on software. So looks like you got a good tool here. Thanks for showing it. And then nothing, they ghost you and they go away and you never hear from them. 

 

Richard Harris  04:06

So so what you’re telling me is you’re trying to solve the being a maybe millionaire conversation your clients are having that we started off with? Is that is that it? 

 

Matt Wolach  04:18

Very true. That whole, “This was nice, we’ll think about it” is one of the worst things you can hear. 

 

Richard Harris  04:23

So absolutely, we’re so so what do you so give some advice? So I’m a sales rep or I’m a sales leader. And, you know, I’m doing all I can and, you know, there’s because I have a belief of why that’s happening are several reasons. But what are the reasons your clients are telling you, their prospects are, you know, giving them all these maybes. 

 

Matt Wolach  04:46

I mean, the number one reason it’s so funny when people don’t have a strong sales background and don’t understand a lot of the dynamics of what makes a good sales conversation. They don’t realize that that end that closing actually starts much, much earlier and Richard came on my podcast, Richard talked about this exact same thing on my show. But a lot of them are what we call feature dumping, or what I call vomiting your product all over your prospect. And they come and they say, Hey, I just want to see what you got to say, Okay, look at this thing and look at that thing. Look at that. And you’ll never truly understand what they actually care about. And maybe even more. So the prospect never fully understands their own problem to a deep enough level, and not enough sales reps are skilled enough, or understand that the techniques available to them to be able to unearth that pain to be able to get the buyer to emotionally feel that pain, and it’s really killing their deals. 

 

Scott Leese  05:42

Yeah, and it’s, it’s systemic, meaning. What I mean by that is, I’ll talk to like a founder, and it’s like a three person company so far, and they have that sales problem, then I’ll go talk to a company of 100 people, and I’m listening to them pitch, and they’re pitching that same way that’s problematic. And then I go talk to this other company that has 1000s of employees. And I’m like, How the hell did you get to 1000s of employees selling this way? So, how does this keep happening when the better way the right advice is out there?

 

Matt Wolach  06:23

That’s a great question. Yeah. Scott, I love that you brought that up, because a lot of my background is in small business. And I’ve had several startups, I’ve been fortunate enough to have some exits from those startups. But it’s really been focused on that smaller end of the world. And I talked to some clients who come to me like you said, they have hundreds of people. And they’re, they’re struggling you having the same sales issues, doing things that you’re like, these are like, quote, unquote, experts, salespeople have been doing this for a while, and they’re still making these mistakes. I couldn’t, it was really kind of a shock to me that these quote unquote, bigger companies, how did they get there? How did they get to that point? If this is it, and really what I’ve come up with Scott is, I don’t think many people truly understand this. And also, they don’t implement it well, or pass it off from maybe the early leaders, because sometimes I see some of the early leaders figure it out, they start to implement it, but getting to that next person, and then the next person and especially as a company scales, I would say it’s not a theory, I think it’s a fact. Big companies are terrible, terrible at sales, like, the further away it gets from the early leaders, the harder it is for them to maintain that same level of of care. By the way, just just to take that to the nth degree. I had to talk to Facebook. That is one of your worst experiences ever trying to talk to people at Facebook, it’s like, do you have you guys ever heard of Facebook even like, it’s crazy? And so the bigger the company gets so hard to maintain that capability. 

 

Richard Harris  07:56

Is that a culture thing in a big company like that? Or is it nobody wants to take accountability?

 

Matt Wolach  08:01

I think there’s that I think that sometimes also that might be at the accountability, you don’t empower your employees. When you get bigger. 

 

Scott Leese  08:10

Listen, Matt and Richard and Scott started a company today. Okay, nobody knows who we are. There’s no branding, or anything like this, right? We have to sell our ass off. We have to do it the right way diligently. You go to a company like Facebook and like what’s up, Matt doesn’t Scott from Facebook. And you get lazy, and you think that the brand is going to do the selling for you, or the product is so well known and so amazing that it’s doing the selling for you, therefore you start to skip steps, and you get lazy with it. 

 

Matt Wolach  08:51

I literally did a YouTube about that exact same thing, Scott, maybe two or three months ago. And what I’ve found from talking with these companies is the best products have the worst sales, because it’s too easy. You’re lazy, like people come in, you don’t do everything, right. But they’re like, yeah, it’s a really good product, I’m gonna sign up, or I’ve heard from my friend, it’s amazing. So I’ll just do it. And the problem is, is that those other products that are kind of coming up the ranks that are kind of growing and learning and guess what, especially in software, things change fast, and they can get better, and they can improve, and all of a sudden, now their products better, but their sales team has gone through the grind of not having the best product. So they know how to do these things. They know how to how to get a buyer to feel really emotional about their problem. And they know how to get that deal to happen quickly. And so now you don’t have the best product and you don’t have the best sales team and that’s a bad thing. 

 

Richard Harris  09:39

Yeah. How much do you buy into the macro economic excuse? Well, you know, the sales cycles are getting longer and blah, blah, blah, blah, blah. Or, you know, let me let me rephrase it. The question. There’s always a piece of that the economy when the economy’s bad how much of that is 80% of the excuse now, when in fact, it’s maybe 25 or 30%.

 

Matt Wolach  10:08

Yeah, I’m with you, Richard. I hate blaming the macro. Like, I have so many clients that during bad times during the middle of COVID, we’re crushing it. And it’s, it’s, it’s, you can blame the macro. But as soon as you start getting into that mindset, then you’re not going to be focusing on how can I get better? How can I improve what we’re doing? How can I grow this business? Because you’re just thinking, well, it’s not gonna work, whatever I do is not going to work. Because we’re in a bad time right now. I don’t like thinking about that. I want to be constantly hustling constantly getting people on the phone and closing deals. 

 

Richard Harris  10:38

Love it, love it. Let’s let’s just sort of back up like, were you always the entrepreneurs, a kid? Like where did all this come from? For you? Would you know?

 

Matt Wolach  10:48

I don’t I mean, yes, I did have some of those tendencies early on, for sure. And I’ve always been like, leaders on my sports teams growing up. I think the big thing for me is, I played sports, I follow sports, super competitive. So a lot of times when you add talk to a salesperson, I love talking to people who want to win. And they just want to, to be the best to beat the competition. That’s something for me, that was always a big driver. And as I got into software, and started to have my own companies and started to realize I just want to accelerate to get ahead to be number one in the market, I want to win. And it’s less about, I need to make a lot of money. It’s more about that competition side. That’s kind of a motivator for me. That’s kept me going. 

 

Richard Harris  11:37

Like this, you asked me to start the show. So now I’m on fire. So fuck off. By the way, by the way, Cathy told me, I’m dropping the F bomb too much. Is she listening to the episode or just hearing you from the other room? 

 

Scott Leese  11:53

That doesn’t count them. That doesn’t do us any good. We need the download. 

 

Richard Harris  11:57

And so but So Matt, do you hate losing more than you like winning? 

 

Matt Wolach  12:02

Yes, absolutely. And I’m glad that you brought that up. Because that that was a realization for me. When the Broncos won their first championship sorry, Scott. Because once they won, by the way, I was at the game Super Bowl 32 in San Diego in the 90s. And the win was almost more of a relief, like Oh, we didn’t lose, we don’t have to go through that pain of losing. We won. And it was, of course, there was joy. Of course, there was exuberant. It was it was but I did definitely feel the relief. And it’s the same in sales. I’m more glad that they didn’t leave us or ghost us or go to the competition than I am “Yay, We won to deal. And it’s kind of a weird thing. But that’s the way it is losing hurts. And by the way, once I learned that, I was able to use that in my sales. Now we can get people to think about what are you losing by not having this tool, instead of selling the positive? Here’s the things you can gain by selling this tool perhaps nobody cares about. 

 

Scott Leese  13:01

Nobody cares about the game. That’s that’s the thing that I think people get wrong. Everybody’s like, don’t scare me, don’t do this fear kind of stuff. Just show me the good stuff. The carrot only not the stick. But the reality is, human beings are more motivated by what they stand to lose than what they stand to gain. If, if if we had some fun competition right now. And we said to people, Hey, go do this, and we’ll give you a million bucks. Right? But you got to do it for like 30 days straight. Very few people would complete that mission. But if we flipped it and had this, like, extreme adverse impact, if you didn’t do it, all of a sudden everybody’s finishing it. Right? Yeah. And and everybody when they’re pitching and selling is like you’re gonna get this you’re gonna get that it’s really like you’re not doing something is going to cause this. doing the wrong thing is going to cause that impact. All of these things are at risk. That’s what moves people to take action, in my opinion. 

 

Scott Leese  14:29

 Yeah. I want to go back to something you were talking about? Because you were talking about playing sports and competition and all this. And I was sitting here thinking, man, if Matt’s not careful, he’s gonna get canceled real quick. Because all of a sudden, it’s you’re not allowed to be like, I was an athlete and I was a competitor. And all this kind of stuff is like we’re you know, we don’t need that kind of environment anymore. Those types of people. You know is not what sales is all about anymore. How do you feel when you hear that kind of stuff because I’m like you, I played two sports in college, I grew up this way playing every sport under the sun, I am the most competitive person that you know, you’ll meet. I can’t stand losing don’t care what it is. And I’m like, Man, I better keep my mouth shut about this kind of thing these days, because all of a sudden, all the voices out there are saying some different things. So I’m curious what your what your take on that kind of stuff is. 

 

Matt Wolach  15:39

I’ve never I’ve never felt beholden to cancel culture or anything like that, I say what I feel. And that’s, that’s kind of the way it’s gonna go. A lot of my clients love that I have that attitude. And I help them incorporate that. One of the ways that I think about with my own teams, if I look back to building my software sales teams, the way I engendered that, that competition within the team was I liked it. As if I’m a big golfer, as if we’re a golfer, group. And when you’re a golfer, you want to beat your buddies in the group. But if their ball goes into the woods, you go help them and you go help them find the ball. And if their swing looks a little off, like your elbow kind of looks a little inside, whatever it is. So you want to win, but you’re also helping. And I kind of tried to create that atmosphere amongst my teams, where we’re going to show you what the scoreboard looks like, you’re going to know who’s on top and who’s below. But we also expect that if you uncover something that you say to a prospect, and it sounds amazing, they love it, it resonates with them. Share that with the group, let’s let the tide rises all boats, but we still want to make sure that you want to win. So it’s definitely an interesting thing. 

 

Scott Leese  16:40

I used to describe that as I want to compete against you and I want to beat you, but I want to beat you 100 to 99 I’m not trying to beat you like 100 to one that does nothing for me. I don’t feel any better about myself. You’re not getting any better. Right? Like, if you and I have some sort of goal to you know, make X amount this year. I want to both both of us get there but I want to beat you by a buck.

 

Richard Harris  17:12

yeah, I just got to write this down memo to self do not play golf with Matt. It sounds like he’s really really good.

 

Matt Wolach  17:21

I don’t know about really good. I enjoy it a lot. But you know, living in Arizona, it gives me some help having year round. 

 

Richard Harris  17:27

Don’t you? Don’t you just love frustrating yourself every day on the golf course. I mean, that’s really what it’s been. It’s been really it’s like, it’s like being a Buffalo Bills fan times 10.

 

Scott Leese  17:36

I really walk into the Hornet’s Nest today.

 

Matt Wolach  17:49

it’s interesting, because I’ve had, I don’t know how I realized that that was the culture that would be good for a sales team. But it worked. Our sales team was amazing. They were helping each other that they were all trying to be that top guy at 100. But they’re also trying to bring everybody else along at the 99. And I had a sales rep say, Hey, I’ve been a part of several sales teams, this is the best dynamic I’ve ever seen. 

 

Scott Leese  18:10

So  it’s tricky, though, if you start to to grow the team, or you inherit people on the team who are like, I’m not competitive.

 

Richard Harris  18:19

You Yeah, yeah. I was gonna ask about culture. How do you build this culture that’s competitive, but doesn’t turn toxic? I think that’s the cancel part. Right? You can build a competitive culture, you just can’t make it toxic. And it can’t be a bro fest. Right? So what is what is your approach to that? 

 

Matt Wolach  18:42

So I like rewarding people when I see good things happening and doing it publicly. So if I have a rep or you know, I believe in a sales team as a whole team, you’ve got the operations people, you’ve got some of the assistants that are helping drive, you know, some of the some of the other tasks, and I want all of those people to be competitive. So Scott, if you are asking that question, somebody said that they’re not a good fit for the sales team. Like I want them to feel like as a team, we need to beat the competition. We need to be excited when we win deals against the competition, whoever it is on the team, and that we’re a team. And so how do I engender that culture? Well, whenever somebody does something well, whether they close the deal themselves or they help someone else on the team do something well, they shared something that somebody else won with. I glorify that and I say Richard shared with Scott a tactic that Scott went using crush it. So Richard, you’re amazing everybody celebrate Richard yada, yada. That’s something I want everybody to see that we we really boost people up when they do something well, like sharing successes with the team.

 

Richard Harris  19:44

I love that. Having having worked. Having worked with Scott and having worked for Scott, Scott is a big advocate and executioner of that style. He was always about you know, that’s a knowing your knowing your pitch and Finding that one spot that you would change get you to ask you why you changed, it would always turn out. I thought I could go faster. I got lazy, like that was the answer. But then he’d say, Okay, go listen to Henry, or, you know, go listen to Colby, and how she says it, and then really advocating that, that cross communication of success story. So I love that. I really like that. 

 

Matt Wolach  20:23

Yeah, and also, you know, to the point of bro culture, I think that that’s obviously a thing that people think about in in software. Obviously, lots of guys in sales, lots of guys, they just kind of lean that way and fewer females do. But I’ve had great women on my team who are amazing at sales, and they’re very competitive, and they want to beat the guys almost more than the guys want to beat them. And you can, it’s not like they’re not out there. They’re there. And it’s just a matter of me just finding the right fits, they’re going to be great to the team. 

 

Scott Leese  20:54

So if you had if you had a team right now, and you’re starting a team from scratch, how are you attacking your go to market motion differently today than you would have done 5-10 years ago? 

 

Matt Wolach  21:14

I think some of the dynamics for me pendulum has swung pretty far. And I don’t I don’t want to I don’t necessarily think that’s important. I’m, I’m building a team, I want to find the best people, I don’t care what they look like, I don’t care what what they’re made of. I don’t care what their background is even. 

 

Scott Leese  21:30

But you know, I have a tactic. But tactically, I mean, more tactically, like, what are we doing? How are we attacking this? Are you having everybody make 100 calls a day back back? Like you did back in the day? Is everybody? Is it a silent sales floor, where the only thing you can hear is people typing away? What?

 

Matt Wolach  21:53

I love people on the phone. 

 

Scott Leese  21:55

Go on a modern day, walk through a modern day sales floor real quick, and tell me how many people you hear on the phone, compared to how many people are typing away. So that’s what I’m saying, though, like, if you were going to build one today, would you build it any differently, not not so much the structure of it, but just like tactically, the channels, they approached the messaging, 

 

Matt Wolach  22:17

the only thing I think about with that is I build it towards the market. So if the market is a great market for cold calls, we’re calling it I don’t think cold calling is dead, I have several clients who are crushing it with cold calling. I know several partners of mine who are doing great with cold calling. If the markets not great for cold calling, we’re not calling. It’s not it’s not a good thing. I’ve been in markets where cold calls don’t do anything. And we’ve tried. But maybe you’ve got to figure out if you talked about go to market? What is that thing that’s going to hit with this market? What’s going to? Where are where are they living? Where are they going to be resonating with our message, and that’s what I want to have happen. So it may not be the same thing that I did in the last company, the company before that. I want to make sure it fits for what we’re doing in this market.

 

Richard Harris  23:06

So how do you figure that out? Because I you know, I’ve never thought about it that way. So I think it’s really, really smart. And is that we so often talk about go to market strategy about finding the right, you know, ICP and working on the pitch and figuring out the messages and the pain. And, you know, focusing on founder led sales, you know, if you’re that early, how do you determine like, at what point will you decide that I’ve done enough execution to realize that the best way to get in touch with this person is x, whether it’s phone LinkedIn stuff? How, what what’s your litmus test? 

 

Matt Wolach  23:47

Conversations. 50 minimum before you even start. So when you’re talking about I’ve tried trying this, I want to have conversations with potential ideal fit prospects before I even start selling. And those conversations would simply be, hey, we’re thinking about this. We’re looking at this type. Like if we started a company today, the three of us like you mentioned, Scott, we need to go out and start talking to the market, we need to understand exactly what do they care about? What keeps them up at night? What do they hate? What are they looking forward to? What do they love, and really, truly understand that persona and what they’re after? To know. Not only, you know, what do we need to build for them, but how do we get to them? Where do you live? Where do you guys hang out online? What do you do? Do you go to conferences, do you do this? And that would help me understand our go to market motion. Because now I know where these people are and where I’m going to be able to hit them best. I’ve had clients come to me and say, Hey, I just heard what Brian shared in our session, I’m gonna start doing that and like, that’s great for Brian, that is not a good thing for you. Your thing needs to be this over here because your market if you start doing that, they won’t care. They won’t even see it. You need to be focused on this. And so it’s really, really important to make sure that whatever you’re doing trying to lead gen fits with who you’re trying to get

 

Scott Leese  25:01

Yeah, and people, people, people want to test things and a B test this and that. But what they ended up doing is they ended up over tinkering. They make like four calls have four conversations over, like, that doesn’t work, I gotta try this. They send like eight emails and nobody replies, and they’re like, email doesn’t work for us. They just keep tinkering. And you don’t put in the body of work to have any, like, statistically significant data behind it, you know, you’ve got to put in 1000 Plus calls, probably, you know, you gotta have you said, 50, I would be like, 100 I gotta have like, 100 conversations before I can make any kind of logical, like deduction here in terms of what works and what isn’t working or anything like that. And that, straying off the path that works. Kill sellers, and sales leaders. 

 

Matt Wolach  25:58

And not just sales marketing too it’s the same thing over there. I have so many people like, well, social posting doesn’t work or SEO doesn’t work. Oh, you do it? Oh, yeah. We wrote articles for three weeks straight. Three weeks, dude, SEO like six months is your minimum, it’s probably a year. And that’s all go away. Same thing. It’s the same thing. And I think that too many people are not consistent enough or persistent enough with an initiative. And if they were they’d be much better off. 

 

Richard Harris  26:27

What what do you look for? And what do you coach people look for in salespeople aside from this competitive piece? What are some of the X factors that you like? What are their background look like? Because like you were talking earlier, like, I agree with you, 100%. I actually think women are more naturally gifted towards sales than men because they have a better job, they do a better job of listening. Like they just do, you know. 

 

Matt Wolach  26:53

And not only that women actually scientifically have a better call acceptance rate, a better email acceptance rate, better social, social connection, acceptance rate than men, especially going into certain circles, especially like some of my circles in the software world. You’re targeting developers. They’re not going to really talk to a guy, a woman, a woman talks to them they’re going to answer the phone. 

 

Richard Harris  27:13

Misogyny is live and live and thriving in sales, for sure it is and we need like, Don’t Don’t kid yourself. People are like psychology. Yeah, if that offends you? Well, I don’t know. You know, I don’t turn off the podcast.

 

Richard Harris  27:29

You know, but Scott’s just so excited that Richards on rants today, I can tell.

 

Richard Harris  27:39

So, so what are the others but let’s let’s talk about skills, let’s talk about or, or personality things like I have a belief the teachers are really good at sales, because they’re very good at slowing stuff down, explaining it to a child mindset, which oftentimes, that’s what you’ve got to address at a business situation, someone doesn’t understand your value. So you have to slow it down. But who are who are some of your favorite people to recruit?

 

Matt Wolach  28:09

You know, what’s kind of interesting, it’s I, over the course of my career, I’ve had a shift on this, but I wish I would have known it earlier because I lived it myself. So my favorite people are customer service people. And here’s why it sounds weird, because it doesn’t seem like a sales dynamic. But what I’ve learned is that the best sellers are the best helpers. And Richard, you and I talked about this. There’s people who just come on and like, oh, buy my thing, because it’s got this. And this. And this, don’t do nearly as well, as the person said, Hey, tell me about what you’re struggling with. And I want to really understand, like, What’s kept you back? And why is that happening. they want to help that person, if we can focus on how we’re going to help somebody, and how we’re going to solve all their challenges and get them to their goals, they’re going to be much more likely to want to work with us, they’re gonna be much more likely to purchase our thing, then just pushing a product on them. And so similarly, I want to find people who want to help who want to get people to solve their problems, who want to feel that joy when somebody does solve the problem with your tool, and they’re able to say, hey, this was amazing. Thanks so much for getting this in my hands. Those are the people that I want to get onto my team. Yeah, they should be competitive as well. But they should be focused on helping and not focusing on them. I, I tell my clients focus on their outcome, not on your outcome of this call. And when you can do that the call is gonna go much better. 

 

Richard Harris  29:27

It’s interesting, because I think people over index on the oh, you know, why do you like sales? Oh, I like helping people. And I came from a generation of like, well, that’s a terrible attitude. Right? Like, like, like, I’m not here to help people. I’m here to close business. You know, and, and maybe, and again, like, I know, where I was as a leader, as a salesperson, you know, how I learned to shift away from that. But how do you find that difference? And I know Scott’s got another question. But how do you find that difference between someone who wants to overly help which could be a great Customer Success person versus they want to help, and they still have the drive to go for the clothes. 

 

Matt Wolach  30:07

I mean, I think of it this way, I, first of all, you have to be confident in your product, whatever you’re selling, if you don’t believe in it, if you don’t think it’s great, if you don’t think it’s going to help get out, or fix the product. Because if you’re if you don’t believe in it, then it’s not going to work, you have to have that belief for them to have the belief. Now, once you have that, then you think that if they’re between you and the competition, then it’s in their best interest to choose you because you have a great product, you have the best tool, you have the best service, whatever it is, and so you want to help them and in order to help them they need to choose your product. So it kind of combines that help need and the competition, you know, if they choose the other product, and I’ve had this feeling, I know when I’ve lost deals, and I think they went to that product seriously, like they’re gonna hate that everybody that comes to that product from or comes to us from that product. They talk about the terrible service they could ever give them on the phone and talk about how it takes forever to do this so that they’re gonna hate life. And I’m so sad for them, that now they’re going to go through that pain. But I also blame myself that I didn’t do a good enough job of helping them understand why they need this tool versus that. So I think it’s kind of Richard to answer your question, marrying the competition desire, but also making sure we can help them as much as possible.

 

Scott Leese  31:20

That’s the sweet spot that you’re that you’re trying to trying to solve for you over index too far on one or the other. Gets dodgy real quick.

 

Matt Wolach  31:28

Totally agree. That’s why sales is easy. That’s why we have jobs, guys. (laughing)

 

Scott Leese  31:34

Right? We don’t deal with maybes as sales has ever been easy. Oh my god, exactly. Listen, this is the part of the show where we usually flip things around a little bit and say how can we be helpful to you? Do you have any questions for us? So fire away, man? How can we? How can we help you? Do you have it? 

 

Matt Wolach  31:54

That’s awesome. Two amazing sales leaders right in front of me. So let me ask you, what do you guys feel the shift in the past few years in the culture and the dynamics? How has that changed our sales motion?

 

Richard Harris  32:10

I have a couple of thoughts. Are you want to go first? Scott? Yeah, I’ll go first, you hog the mic most of this whole episode. So let me scoot you out of the way for a minute. Wait, before you say something I just kidding.

 

Scott Leese  32:25

I mean, the most immediate change that comes to mind, of everything that has happened is the shift towards remote workforce, and sales people and sales teams,predominantly working remotely. Even if it’s a hybrid hybrid situation now, you’re still trying to learn remotely. And I’m a big fan of remote work, I can’t fathom going back into the office ever. But But I am very glad I didn’t get into sales coming up and having to sit at home by myself as a, I was 27. When I got started in sales, I didn’t know anybody. There was no network, there was no podcasts, nothing, there is 0% chance that I would have succeeded. I think I only succeeded because I was around a bunch of other people and can learn through osmosis or steal their kind of Mojo is literally something I used to think about Matt closes a deal, I’m gonna go get my high five just so his like, positive energy can rub off on me. And all of that that immersive kind of experience. That’s the biggest of all the changes in the last five years to me over AI every This is the biggest change to me is salespeople now operate on their own predominantly. And sales leaders are having to learn how to manage people in a distributed fashion. And they can’t put the same amount of time and energy and effort into them. So far, the tools and tactics to get really good at this stuff. Have not caught up to the need. And there’s very few organizations that have pulled it off and done it really, really well. If you’re a veteran, fine. You know, you don’t need it as much. If you’re Junior, that’s pretty hard man. Imagine building a entry level sales or right now full cycle salespeople, or imagine building a fully remote distributed SDR team right now of 23 year olds who just graduated. That’s, that’s tough. So that’s the biggest shift for me of anything. And I do not think that the industry has done a good job of arming people to be successful still in this kind of environment. 

 

Matt Wolach  34:49

I mean, I echo that you’re so right about how there’s just an energy of a team when you’re all together and somebody does something great or you can kind of feel when things aren’t good. You got to pull together and make it happen. I think that that’s huge. But even like outside of quote unquote the office, you that team goes out on a on a dinner because you celebrate an amazing month or a quarter or you go out to to do race karts. And because you’re just celebrating, having a team outing, the bonding that happens or just even like after a bad day, you go to happy hour with a couple couple people on the team. And that, that, that, that creates that dynamic that’s so strong. 

 

Scott Leese  35:25

It does. But even I’ll play devil’s advocate and just say like, well, I don’t need the bonding because 20 Somethings do not socialize the same way that we socialized when we were 20 Something they just don’t they interact with it with and experience the world in a very different way. So let’s just for the sake of argument, say that that bonding camaraderie part doesn’t doesn’t matter so much. It’s all these little moments though Richard calls them the in between moments, it’s when you go go kart racing. And people are talking about their deals, and helping each other and talking about this thing and that thing, or we’re venting about something and saying, You know what, I saw that this way. They’re actually talking about work, when they’re doing these kind of bonding, camaraderie, kind of things. And so so that’s peer to peer coaching or mentorship, you know, leader coaching, those opportunities disappear, predominantly in remote kind of environments. And listen, my opinion, the genies out of the bottle, it’s not going back, there’s not going to be some return to Office movement, in my opinion, whatsoever. You could try to force it, but there’s no way. So we have got to figure out a way to empower people and get them to learn and succeed in this kind of environment. This is the biggest challenge to me in the last five years over everything else. 

 

Richard Harris  37:01

The challenge I see is, is the same challenges even existed before this remote piece, which is nobody’s teaching leaders how to be leaders. Nobody’s teaching managers how to manage humans. There’s no soft skills and development, right? You got people like me and Scott, and, you know, you know, sort of the, you know, the elders as we’ve hit that stage of our life, where we never had to figure this stuff out. Like, this didn’t matter. And we also sucked at managing people for a long time. Right? We used all the terrible things of you the only the only thing you know, the day, right, exactly. So, but nobody taught me how to actually manage a human. Nobody taught me, you know, how to tell someone which I had to do once, you know, you know, oh, they’ve got a body odor problem. And it’s affecting everybody. Like nobody. Nobody taught me how to have that conversation. Nobody taught me how to be empathetic for someone’s personal situation, and not try to flip it into the Okay, well, you know, I know you went to the hospital, you think you can take another call real quick. You know, nobody taught me that stuff. And it’s even harder when they are remote. Right? So I think so this, this lack of teaching has existed forever. And now it’s just a new issue that we don’t know how to do. Because it’s even a much harder issue with this remote piece. So, so So I agree with all of it. 

 

Matt Wolach  38:31

It’s very true. It’s critical for people to be leaders, and they’re just not finding out how. 

 

Richard Harris  38:34

yeah, the other thing that I would say, that I’m seeing today is, you know, 2024 is just turned into 2023 part two, right. everybody got to the end of 23, thinking the economy’s gonna get better. Everybody was why people thought that, who because they thought that because because they thought the interest rates were gonna start to get cut, which, by the way, is a quarter point. Right? Like, I don’t know that, you know, that’s, you know, it’s just good news. That’s basically it was something that they could hang their hat on. And so everybody started smoking hopium on this is kind of silly. Yes, the the and then the other pieces aside from the, you know, thinking the economy is going to get better. Nobody has adjusted that the sales cycles aren’t enlongated. They’re not taking longer. The sales cycle has just straight up adjusted, but our mindset has not, we have not adjusted our forecasting capabilities based on real data. We’re just again, smoking hopium that, oh, the sales cycles will still get shorter, when in fact, you should build your revenue target around longer sales cycles. And when you can adjust when the sales cycles actually adjust. But until then, stop thinking your old school 45 days six sales cycle is gonna keep working when in fact it’s taking you 65 or 70 days.

 

Richard Harris  40:05

So we, we flew by Holy shit. This has been 48 minutes of this conversation. So Matt, you’re like, I was texting Scott like, this is a great episode because days, he’s good at this. You’re our guy almost almost like he’s done. 

 

Scott Leese  40:19

It’s almost like he’s done it before, maybe once or twice, guys once or twice once or twice.

 

Richard Harris  40:25

You know, so we’re super grateful for you to come along and you know, we gladly accept your maybe for next year. You know, we’ll you know, as much as we hate it will. It’s hard, maybe too hard. Maybe. 

 

Matt Wolach  40:38

But I think it was a great it was a great conversation to upgrade to a hard possibly. Alright, how’s that?

 

Richard Harris  40:50

That’s like winning the Super Bowl.

 

Richard Harris  40:52

But how can how can people get a hold you Matt? 

 

Matt Wolach  40:55

Yeah, sure. So I’m very active on LinkedIn. Matt Wolach W O L A C H, you can also go to Mattwolach.com. And I’ve got giveaways like a scorecard where you can kind of plug in your numbers, and it gives you benchmarks of what you should be hitting and how well you’re doing against it.

 

Richard Harris  41:09

That’ll scare everybody. Nobody wants to know that.

 

Scott Leese  41:12

Nobody wants to see how hard is going to be. But the right the right person will find it. And yes, that’s correct. All right. Thanks for joining us, Matt. We will see everybody next time on the next episode of The Surf and Sales podcast.