Michael Wills on Breaking the Founder-Led Sales Ceiling

Transcript

0:03 We have another episode of Tailwind. Today we're joined by Michael Wills.

0:07 Michael, tell us a little bit more about yourself.

0:09 Well, thanks for having me. So, Michael Wills, I started a firm Topline Solutions as a fractional VP of sales

0:17 about 10 years ago, a little over 10 years, and uh working with primarily small business owner founders to build great sales organizations.

0:27 Nice. Yeah. And and before the episode, we were talking a little bit and you're talking about early in your career. Uh I think the phrase was, you know, it go

0:34 with God and come back with money and that was all of the direction you were given. Uh tell me a little bit more about that uh that scenario that you

0:42 found yourself in and kind of what happened when you were experiencing I guess that lack of support.

0:47 Well, you know, it's a true story and and so I did work for a company and and it isn't unique. you know, they had

0:54 absolutely no sales strategy built out, and they just expected the sales reps to go out in the field and and bring back

1:02 business. And as a sales team, we kind of phrased it, go with God and come back with money. And I would jump in the

1:10 company car and I'd make a bunch of sales calls during the day and I'd close business and and create a a unique

1:18 product with a unique pricing model and I'll excitedly come back to the office and and say, "Here's our new client."

1:25 And then they'd look at me and uh then they'd have to figure out, "Well, what did you sell? How do we implement this thing? And how do we make money off of

1:34 it?" And um you know it's I realized that the leadership

1:42 really delegated sales strategy to the sales team and to me as as a sales rep

1:51 and and how dysfunctional that was. And u I went off and um created my fractional sales uh business

2:00 10 years ago and uh I started hearing a lot of the same stories. I could see in the in my clients that the sales reps

2:08 were prospecting without real clarity on uh who the right client was and why. And

2:17 um and it was, you know, the the owner, the founder instinctively knew who the right clients were. They started the

2:26 business. They um they closed the new the first clients. they knew their products intimately and how it would help the um how it would help those

2:35 companies and yet they never communicated that that insight to people in the organization. Um, and so then

2:44 what would happen is the owner would um, you know, sales reps would go out and and create it uh, and try and identify

2:52 what the right ICP was uh, for the business. And then the owner would do one-on- ones with them and get really

3:00 frustrated that they were seeing this pipeline full of opportunities that weren't a fit. And so owners would then, you know, tell me this story about how

3:08 doing one-on- ons and they get really frustrated about these poor deals. And I asked them, I said, "Well, is that a

3:15 sales problem or is that a leadership problem?" Right. What was the typical answer that you got? Well, it stopped them.

3:24 Just dead in the tracks. It stopped them in their tracks because you know it's not the salesperson's responsibility to

3:32 figure that ideal client out. It's leadership's responsibility. Leadership developed the company. They created the products. They built the whole model around who they want to service and why.

3:44 And you know who are we uniquely built to help? what are the products and what are the the buying signals and buying triggers that that are the the the right

3:53 time to engage um you know what makes us different and why are we different and

4:00 uh and sales can't be responsible for solving for answering those questions it's got to be it's got to be leadership

4:08 and uh and I think that once leaders go through that exploration process and help map that out and then communicate

4:17 that then prospecting can really happen uh you know effectively and and ultimately sales people can can happily sell.

4:25 So if you have a a sales leader right now who's listening in and they're wondering gosh is this me? Is this my problem? What would you kind of

4:34 recommend be like some questions they can ask themselves? Some things that they can look for uh to start to diagnose that hey we really need to fix

4:43 this specifically. It's actually not, you know, maybe I've identified five different things, but after thinking about, you know, what Michael's told me,

4:51 these three things have totally set off the red flag or this one thing or I don't whatever it might be. Is there a specific thing that a leader can kind of

4:58 put themselves through to start realizing, oh, all right, that is my problem. I need to start directly addressing it.

5:05 Yeah, it's a great question. So, you know, I work with a mindset that um you

5:11 know, there's founder sales ceiling and there are contributing factors to why

5:18 founders hit that sales ceiling and they uh factors like they're still overly

5:26 responsible for the sales revenue. Um they're challenged with they they've hired people that they believe

5:34 ultimately are the wrong people. they don't recognize oftentimes that it's a sales infrastructure that is the problem

5:41 and not necessarily the people that are the problem. So I think that you know leadership needs to recognize that they

5:49 define strategy, sales delivers the strategy and prospecting executes that original

5:58 strategy. And it's really it's a um it's a core element. Once they have that built out, then they can start

6:07 installing the processes, the tech stack um to be able to then execute what what the leadership wants the sales team to

6:16 do. And that's the the struggle. It's that um I like to say founders have have almost

6:23 never been heads of sales, right? So they don't it's just not it's just not an experience set that they usually have. They great they're leaders,

6:32 they're product developers, they're financial people, whatever, but they've really never been head of sales. So it's it's a challenge for them to recognize

6:40 the deficiencies in their sales organization um and why their sales organization oftent times

6:49 um significantly behind this the the structure and quality of operations. the structure and quality of finance and um

6:58 but be because they they don't understand how sales really works. They haven't built the organization that will

7:05 allow it to be an a a team that is at least as good or if not better. In my mind, sales has to be as good or better than operations and finance.

7:16 Yeah.

7:16 And um it's got to be the driving factor of the organization. And when it is, that's when you scale rapidly.

7:24 Yeah. So, as somebody who has spent most of their career in the operations side, uh mostly because when I started, I had

7:31 a couple sales jobs and I had a very similar lack of any sort of strategy or direction. It was, hey, here's this, you

7:39 know, membership guide for the Oregon State Bar. Go call everybody. And I was like, what am I what am I doing? And it was like, just call them. You'll figure

7:46 it out. Like, good luck. And then like I had another one and it was this over and over and over again. So I was like, "All right, I'm getting out of here. I'm going to the op side." And from somebody

7:54 who's on the op side, uh you can have the best ops team in the world, but if your sales team isn't delivering, it does not matter. But uh alternatively,

8:04 you can have a great sales team and a bad ops team and you'll do better than the the team that's opposite. So yeah, as somebody who spent most of their

8:12 career on the other side, I could not agree more. Even though my brother should be or I should be like defensive over the territory be like no you have

8:19 to have hops first like no you don't. Um so as you know as somebody who is a founder that's leading like or is

8:27 running founder le sales is it is it something where like you know wait till this point to start doing these things

8:34 or is there no is it never too early to be considering what you're talking about right now and if you have a founder that says t and you feel like there's any gap

8:41 here you should stop everything and work on it today.

8:44 Yeah. So, I think that there's a um an initial window that you've got to build some things internally. Yeah.

8:53 Um and then you reach a point where you can start to see the dysfunction, right?

9:00 You're you're you're continuing to have referral-based leads and not company

9:07 created leads. Um you're not having conversations with new companies. you're trying to hold on to your existing

9:16 clients and uh and you're realizing that there's no there's no more growth there.

9:21 You're you know the growth of a client is offset by another one client another client leaving. Right? So once you start to see

9:29 that phase and you start having um a budget an annual budget meeting where you say oh we're going to grow 8%. And

9:38 somebody from operations says well how's that going to happen? we don't have we don't have a sales team that's that's driving opportunities you know that that

9:46 that's organically growing. I think that's when you start seeing uh that and then you you combine that with the

9:53 founder constantly being responsible for revenue generation and I like to challenge

10:01 founders and saying okay so if you took 90 days away from your business what would happen to it? Mhm.

10:08 You know what would happen with revenue generation and you know vast majority of them say it would completely fall apart.

10:14 So if the answer there you can start to see those are the questions the self-reflective questions to uh to

10:21 identify when have I hit that foundersled sales ceiling is that I'm as a founder I'm far too involved in revenue generation. I don't have a team

10:30 that's operating independently and as structured and organized as effectively as other departments in my company.

10:37 Other departments and people in my company don't believe or trust or value the sales organization. We're not having

10:44 new conversations with companies. We don't have a pipeline of quality prospects that fit the opportunities that we would want to see and we would

10:53 like to embrace and bring into the company. If you're hearing those things and you're getting those wrong answers, I think you you're starting to see that

11:00 you're, you know, you need to do some work and and and get in there and rebuild your sales organization.

11:06 Yeah, I think those are great straightforward. Those are pretty easy to self diagnose and realize I got to make some changes. Um especially that if

11:13 you took the x amount of time off. I've been because you I think you just said 90, but like even 30 days it probably would start to falter and fall apart. 90 is a long one.

11:22 Yeah. Yeah. uh as a as my own entrepreneur sometimes I think about a week freaks me out so I'm not sure what

11:28 to do but you know I'm earlier than that uh but but I've had I've had clients where um

11:36 you know beautiful companies huge machinery great facilities

11:42 uh 30 40 50 70 employees and I meet with the owner and they'll tell me well last

11:50 week of the month I need to call up a bunch of companies a bunch of customers and get some new business so that I can cover our our budget shortfall and make payroll.

12:00 And I'm like, "Wow, that's got to be incredibly frustrating and scary." You know, you're sitting there want, you know, looking like I'm personally

12:07 responsible after 20 years of um of maintaining that revenue flow to cover

12:15 payroll, then I have a serious problem in my company. Mhm. What are uh some of the things that you know if somebody's

12:23 sitting here and they're going, "Oh god, that is me." And like obviously they can call you, that would be like a great first step, but if somebody's like, "Let

12:30 me kick the tires," you know, and especially as like, you know, somebody who's a founder, they're probably going to want to try to get their hands on some stuff. They're a founder after all.

12:38 Um you know, what would you say is like what are some good initial steps, some good initial things that they can start doing to to start getting themselves out of these situations?

12:48 I think it, you know, again, we both agree that it starts with with um being

12:54 able to sell um outbound, you know, having having this. So, the first thing

13:01 is is who do you sell to? And a lot of companies really struggle and leaders need to recognize that, you know, an ICP

13:10 is far more than revenue, geography, um, industry, and number of employees.

13:19 And that's really the ICP for a lot of a lot of smaller businesses. Um but ICP is

13:26 really about why should somebody do business with you and understanding you know uh the buying triggers the buying

13:34 triggers the business problems that you solve. Why are you better than the competition?

13:39 Um how does your price point fit the uh who the um you know the buying company uh you know fit within their business

13:48 model and why does that why is that the case? So I think you know founders, business owners need to see what kind of

13:57 clarity do we have for that you know how as as an organization and if not address that first I believe in strategy

14:06 structure process tools and people and unfortunately

14:12 um so many times uh people are what's identified as the problem And we've

14:21 hired five people. We've fired four of them after uh 6 months. Nobody can nobody's a fit. Nobody understand. They didn't bring a rolodex. They didn't

14:29 understand what we do. And then I recognized that you don't have a clear sales strategy. You don't have sales processes that fit that sales strategy.

14:40 You know, you don't have a tech stack.

14:41 In today's world, you better have a pretty solid tech stack uh to enable your your the people to execute that

14:48 sales strategy and the processes that you want and then and then the people properly incentivized

14:56 uh to uh to be able to execute what you're looking for them to deliver. So, you know, I I think as an owner to

15:04 recognize that it's systemat systemic, right? It's a series of things that gets to success and it's going to take some

15:12 time. It's not a a six-month suddenly we, you know, we're going to be able to have a great pipeline and and we're going to be successful and start to see

15:21 new part new customers and revenue. It's a process, but I think owners need to recognize that it starts with who are we

15:29 and why are we good and why um why should somebody want to uh to talk to us?

15:37 uh you know it sounds like if you don't start with a strong ICP definition there's really you're never going to quite get to the to the top of the

15:44 mountain from it and the an a common problem if not the complete lack of an

15:51 ICP is not the fully developed ICP. So if I'm trying to build that out further, I mean is there would you say like

15:58 there's a certain level of depth or full explanation that you can actually get to and you know be like okay I'm satisfied

16:06 or I mean is this this continuous process of always being refining and adding and continuing to look at you and how do I make sure that I've built my

16:15 foundation of understanding my ICP fully before, you know, going downstream and messing around with too much stuff.

16:23 Yeah. So I I think you know you can do it the manual way so to speak which would be to really look at your your top

16:31 customer base and uh and revisit the sales process uh and if you have any documentation if you've got emails

16:40 anything that would allow you to understand the customer condition what those conversations sounded like what

16:47 the pain that they were experiencing how did you convey uh what you could do to solve that pain if you can, you know, go

16:54 back and and regurgitate that information, uh, and then map that out over a series of several customers, then

17:03 you can start to really pick nuggets of that. Um, and then be able to validate what your ICP is. Uh, I think that's

17:12 really helpful. Um, in today's world, you've got AI, right? So um so AI accelerates this process and it you know

17:21 if you've got that thinking that you're going through you know once you and I've got you know um a client that we're

17:28 implementing this today. So um we have uh clarity to our ICP what we believe is our ICP. Mhm.

17:37 We're now taking our top 100 customers and we're then bouncing that up against

17:45 an IP ICP scoring model that we built out. Nice. Yeah.

17:50 To be able to validate that those customers match with pretty good, you know, degree of regularity to what we

17:57 believe to be our ICP. Once we've done that, then we have a really good hit.

18:02 Then we can feel really comfortable that when we go out and do the prospecting, we go out and find not lookike companies but problem alike companies.

18:12 You know, you know, companies that are experiencing the same problems that uh our our existing clients experienced before we we started working with them.

18:23 Then we can go out and find a prospecting list pool that we can then reach out to with a degree of confidence

18:32 that they're the right they're the right fit and we can start qualifying them to um to then validate that and ensure that uh we be able to be able to help them.

18:43 Yeah, I feel like the academic like if you Googled it definition of ICP is the fmrraphic stuff. Where are they located?

18:51 How big are they? what's their revenue ban? All this kind of stuff. And I think people stop there. And it sounds like the big hump that you have to get over

18:59 and you'll find yourself in a much better place is the pain the the pain of the ICP, the problem that you're solving

19:06 and understanding that and that being the where people fall short most commonly is getting into that land. Um I

19:14 mean do how much value would you put on the the academic part? Is that something to even hold on to? Is it enough for like maybe some rough guidance or is it

19:23 hey live in this pain similarity and the pain ICP instead?

19:27 Well, I think that um that framework is needed. I mean obviously if your company is more geared

19:36 to working with a smaller company, then you want to have an ICP that we'd like to work with companies between five and 10 million, you know, or something, you

19:44 know, something like that to where you're fit geographically.

19:48 um you know our product really fits the educational system. So we you know that's an industry target. All of that

19:54 is is is true. Um but then you take it to the next level. So once you get past the framework then you take it to what

20:02 are the problems we're solving and um what are the buying signals the triggers what are the events? uh you know we've

20:10 talked about you and I about uh there's certain things that can happen to a company and um government regulation

20:18 hits them or um or there's a uh they get a you know something happens in the stock market or the the housing market

20:26 and that triggers an event that then your customer can then uh satisfy, right? So there's information out there

20:34 that you can find. So um if you can find those triggering events or or systems or you know using systems to do that that's

20:42 really valuable uh to help facilitate and accelerate that. Um so you know

20:49 using AI with a strong ICP helps you evaluate uh and identify the companies

20:56 faster, identify people that are in those uh um leadership positions at those companies faster. Uh, and then

21:05 being able to communicate messaging that's personalized that will convey how you can solve and fix those problems

21:13 because you have experience doing that successful experience and a client base that will tell you that you know um all

21:21 that can be automated and all that follow-up can happen uh faster scheduled so that you're less people dependent and

21:29 more system dependent. But the framework of it is coming out of your head. It's coming out of, you know, a strong ICP

21:36 where you understand why we're why we're good and and who we're good for.

21:41 Yeah. I I think you mentioned it earlier either while we're recording or before and hopefully not before because it might be hard to reference, but um

21:49 timing being so important and it being like right now being the important part and there's nothing better than hopping on a call with a prospect and they're

21:57 like, "Hey, this is great timing." And that's like bing bing being like this is going to be a great you know discovery process that we're probably going to close it at a higher rate than if they

22:05 didn't mention something like that now is is that something everyone's going to say if it really is the right timing maybe not but it's such a good indicator. Um if I'm

22:13 I think you know I think that you know we we have to remember the basics of selling.

22:20 Yes. which is helping somebody do something they can't do for themsel at a time that they needed, right?

22:29 That's sales. That's, you know, that's the most elementary definition of selling is is is exactly that. And I

22:37 think people, you know, make it all complex, uh, overly complex when it's

22:44 really about that. It's it's it's about, you know, uh people made shoes in, you know, hundreds of years ago because the

22:53 um the cobblers made shoes because somebody else didn't know how to make a shoe or didn't want to make a shoe. They wanted to work in the field. So, they need So, it really gets back to those

23:02 basics, right? And um and I think that everything is an enabler on those on those basics.

23:10 Yeah. No, I that's love the simplicity in that because that's what it boils down to. there's a lot of ways that you can be more skillful and artful around

23:16 it. Um, and helps helps illuminate all of it. But at the same time, it always comes down to that fact. Um, for

23:24 somebody who's looking at their ISP and they're like, uh, bought in on this, like I want to reach out to the right person at the right time. Um, and then

23:33 they're kind of like, okay, but how do I start to figure this out for myself? Do you have any recommendations on like a brainstorming activity or a way to

23:41 gather data or something that they can do to start identifying those ways to reach out at the right time?

23:50 Um, so I definitely think that leadership should take the lead within the company but then bring sales in on

23:57 um, uh, what kind of conversations they're having so that those two, you

24:02 know, that can match. Um the uh the

24:11 the salespeople need to create the processes to be present and to be able

24:19 to uh systematically, you know, the adage that it takes eight times of communicating with somebody before they you can really connect with them, right?

24:28 And um and the the fact that most people stop after the second attempt. So you know and I don't blame them when you

24:37 have no idea whether it's even the right prospect right but the more definition you have and clarity towards the right

24:45 prospects the more confidence your sales team has towards making that sixth seventh and eighth attempt and and

24:52 putting the effort to that as well. So um you know once you have that matching

24:58 of of activity to to message and and strategy then you know it all really

25:06 starts to come together and the salespeople feel better about what they're doing and they remain motivated.

25:13 Prospecting is difficult be to maintain your motivation and um the more

25:19 confidence you have in in who you're the person you're trying to reach out to is really the right fit, you're far more

25:28 motivated uh to to make that next call, make that on-site visit, get on that airplane, you know, whatever that is to

25:36 to make that, you know, continue to try and make that connection, the more confident you have that it will lead to

25:43 a positive outcome, then you're more willing to do the work.

25:48 Yeah. I mean, you're like, am I really going to make this, you know, 10th, 12th phone call when I actually don't in my heart of heart believe that this is the

25:55 right person to be trying to reach out to versus I'm on the other side of like a really great deal. I just got to call like one or two more times and like I,

26:02 you know, that right there is intrinsic and you can't really make force somebody into compliance. They're going to start getting like upset with it. Um, so for

26:11 that, you know, instilling that confidence and all of that, what are ways that sales leaders can clearly demonstrate and communicate that things

26:19 are on the right path, especially with, you know, sales cycles typically taking so long that it can have the, "Hey guys, all right, we've made these adjustments.

26:27 We've figured out the timing. We figured all these things. It's not going to be perfect out of the gate, but uh, in 3 to 6 months, you guys are going to start

26:35 reaping the benefits of putting this effort in." And then how can a sales leader then be like making sure to demonstrate and communicate uh to to

26:43 maintain that or demonstrate and communicate the information that creates that confidence for those sales people doing the prospecting.

26:50 Great question. So I solve that problem through the incentive plan and the and

26:57 the targets that we create. The biggest weakness in incentive plans that I consistently see is they're not tied to strategy. Mhm.

27:08 They're just out there all by themselves and they're usually only um focused on results.

27:17 So when your incentive plan is focused on strategy and process, then you start rewarding people for executing what you

27:26 want them to execute. So, um, you can reward people for not only the number of

27:33 calls they make, but the number of meetings to companies that are a fit to the ICP.

27:40 Um, the uh number of demos or the number of proposals that meet what you're looking for. Uh, if you want to um

27:49 highlight a specific product, create this create the uh incentive plan. uh I guess across all revenue obviously but

27:57 in extra incentive for specific products or or geography or industry that you're trying to target. Um, so when you

28:07 measure those things then and celebrate the results of those things, even if you haven't gotten to the top of the

28:15 mountain, you're celebrating the walk up the mountain. And that is, you know, if you don't do that, then you're not going

28:24 to get to the top. You're going to stop, you know, at at a midpoint. So you want to create then incentive plans that that

28:32 match what you're trying to deliver. And when you do that, then people remain motivated. Leadership says, "Yeah, this

28:40 is working. We're getting Yeah, we we you know, we haven't added 15 new clients, but we've had 35 meetings and

28:47 and uh they're they're selling to the people that we want them to sell to and they're having the right conversations.

28:54 Um, and we're and we're measuring that and rewarding that. So, you're when you do those things, you're going to get to where you want to get to.

29:02 Yeah. And as much as like we want everyone to to be perfect and to like have perfect strategy sessions and leadership and get everything right the

29:10 first time, you know, real realistically and people should give themselves grace that you're not going to get everything 100%. So, as you're walking up that

29:17 mountain um and you're making these adjustments, how are you keeping the sales team on board with the adjustments?

29:24 It's it's got to do the the the the weekly meetings.

29:29 Uh you know, the weekly meetings have to be about uh you know, evaluating your quarterly goals, looking at uh things

29:36 that you were expected to do the previous week and did you get them done, talking about issues that are happening

29:43 within the sales team across everybody that need to get resolved and looking at the performance. So having those meetings and then doing the one-on-

29:52 ones. One one more thing I should have mentioned is role playinging is extremely important uh w within the

29:58 weekly sales meeting. Uh I can tell you that I have a client that we started roleplaying every week three years ago

30:07 and over that time we've we've role played product knowledge. We've role played uh applications we're trying to

30:15 fix. We've role played objection handling uh pricing. um discovery

30:23 meetings, all the elements that you you're looking for throughout the sales process. We've role played all of it and the sales team is unbelievably skilled,

30:32 more skilled than they were before. So that's got to be a key part of your of your weekly sales meeting. When you do

30:39 those things and you measure the results through the right KPIs that are part of the walk, part of that like you talked

30:47 part of the journey up the mountain, not just the, you know, the the KPIs that measure being at the top of the mountain, but the KPIs that measure the

30:56 journey up the mountain, then you really are keeping people, you know, focused.

31:02 Leadership is remains confident. uh other c other people in the company remain confident which is really important. you know, having having

31:10 finance and and operations believe that the sales team is is doing the work that they you want them to do to get to the

31:18 top of the mountain and then maintaining the motivation because it's people feel good they are getting there and then ultimately you got to get there, right?

31:26 You got you got to get to the mountain or you have to have a different conversation with it with an individual.

31:32 But you got to recognize that it's a journey and and and by uh identifying it, all the different milestones you're trying to achieve and then rewarding

31:40 people through that process will keep people motivated. And uh and if they're doing that work and you feel good about them and how they're growing, continuous

31:49 improvement, then you're going to feel good that they're going to get there.

31:52 Nice. All right, Michael, we're getting to the end of our time, but before I let you go, uh, I like to ask everybody if they're listening in, uh, if somebody's

32:00 listening into this conversation and they can take away one thing that they just have to make sure that they keep in mind and maybe they forget everything else, they should remember everything

32:08 else. But if there's one thing that they can take with them, uh, what would it be?

32:13 Well, I go back to, you know, the focus of my business is uh to help founders get through the foundersled sales

32:21 ceiling and um recognizing doing the self-reflection of the elements of it. I'm too engaged

32:29 in sales. My sales team doesn't operate independently. I've got high turnover of my sales team because they don't follow

32:37 there isn't a strategy that they're following. uh they're having to do it themselves and they become frustrated and leave. Uh you're not hitting your

32:46 revenue goals. You've you've you don't have a forecast because there's no pipeline that's really validated and there's no sales processes that take a

32:54 deal from beginning to end. So if you're if you're doing the self-reflection and seeing those things in your business, then I really happy to talk to you.

33:04 Cool. Awesome. Michael, I really appreciate you taking the time. Thank you very