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Wise in Five with Mike Hayes

In this episode of The Wisory Wise in Five, we sit down with Mike Hayes — a seasoned sales leader whose career spans CDW, Oracle, Silicon Valley startups, and now Zoom, where he helps shape growth through innovative sales strategies.

Mike shares how mid-sized businesses can turn their agility into a competitive edge, why consultative selling builds deeper trust than transactional deals, and how AI is transforming the entire sales cycle — from pre-meeting prep to long-term client engagement. He also reflects on leadership lessons, the “three E’s” of selling (engage, educate, empower), and the importance of humility in building lasting relationships.

This episode is a must-listen for leaders asking:

  • How can I tailor my sales approach to the unique needs of mid-sized businesses?
  • What qualities define a truly exceptional salesperson today?
  • How can AI sharpen my sales strategy without losing the human touch?

Transcript

Jason (00:40)
Hi, how you doing, Mike?

Mike Hayes (00:42)
I'm doing well, Jason. How are you doing?

Jason (00:43)
I'm doing fantastic. It's great to see we got a beautiful day today. I know we're both in Chicago sun shining a little bit of fall in the air.

Mike Hayes (00:51)
You can't beat this. We've had a little bit of, as you and I were talking about earlier, you we've had a little bit of the decrease in heat, which is a warm welcome after a hot August, but looking forward to the rest the summer.

Jason (01:01)
Hot and humid.

I agree. So thank you for joining us for the Wise in Five And before we dive into the five questions, I thought it'd be great just for you to share a bit about your background and how you got to this amazing journey where you're now at Zoom.

Mike Hayes (01:17)
Sure, absolutely, Jason. You know what? I've been really fortunate. When I came out of undergrad, I had the opportunity to join CDW, which was such a great technology company. And after 14 years there, was really the premise of after leaving the University of Chicago, was more of just looking for more and what I can do to learn more. And it was more about learning different business models and learning different business structures as opposed to the need to change from any one specific company.

But over the years, I've had the opportunity to work for larger organizations such as Oracle and small startups out of Silicon Valley. it's really given me a lot to think about in terms of what type of company I like to work for, what type of products or solution I want to be providing to the clients I get to work with, and what type of partners I get to engage with on a day-to-day basis to scale businesses faster. It's led to me joining Zoom. And I had joined Zoom right at the beginning of the pandemic, which was

Jason (02:08)
Perfect timing.

Mike Hayes (02:08)
It was it was perfect timing. coincidentally, I started talking to Zoom about three months before the pandemic. So I mean, and then all of sudden, the pandemic hit and joined at the great time. But it's been it's been a great ride. Phenomenal company, great people to work with. And and I'd like to think it's probably one of the most innovative companies on the market right now. So it's really allowed us to to bring solutions faster to clients based on what their needs are. And we continue to grow from there. So I've been very fortunate.

to take on a few leadership, growing leadership roles within the organization. And that kind of puts me at where I'm at today.

Jason (02:40)
Terrific. Well, thank you for sharing that. And I think you're relatively unique in our whole advisory network ⁓ on The Wisory because you have this unbelievably deep and successful career in business development and consultative selling. And I really want to dive into that, because I know for a lot of our mid-sized businesses, that is a huge need for them, especially in, we'll call it just these uncertain, uneasy times where

the need to drive revenue is so important.

Mike Hayes (03:08)
I agreed 100 % and you know those mid-sized companies that you talked about, I know that we'll talk more about them but they really are in a unique space and there's pros and cons and I always like to think of it as the pros and we can talk more about that but it's a unique space. I think that they are agile and nimble and they can really take advantage of their size rather than using that as a disadvantage.

Jason (03:28)
I totally agree with you and we'll definitely dive into that. And I'd be remiss if not to call out what a fantastic background you have with the Wisory logo, our Wisory Owl. So thank you for doing that. I got to send you a Wisory hat. Exactly. So my first question, which I really ask everyone is, where do you find inspiration just in daily life?

Mike Hayes (03:39)
It took hours to hang those frames in the right direction and make sure they were straight and get the pictures correctly.

a little bit is going to sound cache in terms of just, know, and I think of like family in terms of just kind of what's what's led me from whether it's my grandparents and whether it's my own parents. I always think of like, how did you grow up and what led you to where you're at today? And, at least for me on a personal level, it stems back to the way I was raised and just, watching my grandfather work with as a tuck pointer who came from Sweden and, and then my father was a fireman and doing, did, you know, construction on the side and

I look at even, where do I get inspiration today? It's even from my peers. I mean, I look at my peers and what are they doing and how are they thinking differently? And I don't just mean peers here at Zoom. I just mean peers I've worked with over the years and colleagues I've gotten to know and folks that went off and started their own businesses or maybe went to a different company. But I look at those folks that, keep me mentally stimulated. The folks that are asking me the questions. And I was fortunate enough to meet up with a few ⁓ former classmates last week. And I've known these guys for about 15 years. They're from grad school.

I just love the conversation. We are talking about ideas for three, four straight hours. And that's the type of ideas and folks that I want to look at because it is inspiring, right? So it's, look at my peers and family for my day to day inspiration.

Jason (04:55)
remember you sharing with me your family and your dad. I think, did you have other relatives that were firefighters as well?

Mike Hayes (05:01)
Yeah, my

dad and a few of my uncles were all firemen. So it's definitely in the family.

Yeah, no, it's been great. The lineage has been great. and I look back at that, you know, I took the fireman's test when I was a junior in college, right, with 18,000 other people at the United Center. And, by the time I had gotten called, which was about two years later, I had already started my career in technology. And it was kind of that crossroads of like, all right, do I go on to become a fireman or I stay in technology? And, you know, if I look back at it, I couldn't have gone wrong in either selection. They both would have been phenomenal career choices.

I just followed my passion at the time and I was really enjoying technology and the sales aspect of it. It has taken me to new heights and given me new opportunities that I'm very fortunate.

Jason (05:41)
Yeah, well, I would also think that in sales and business development, you're putting out fires all the time. So as you mentioned, you've worked at these large organizations, you worked at mid-sized businesses, and you work with a number of mid-sized businesses just as part of your daily path. so

how do you tailor your sales approach and the products that you're selling to address the unique challenges that mid-sized businesses have? And I'd say unique challenges is also the unique needs.

Mike Hayes (06:06)
Yeah, absolutely. When I think of a ⁓ mid-sized business, think of they don't have all the resources that a major enterprise is going to have. It's not that they've got hundreds of people in technology and owning the technology stack. They really have to be conscious of any investments that they're making and what does it mean to their business and if something needs to be sacrificed. So when I sit down with them or the team sits down with them, we really want to understand what's your business like today? Where do you want to be tomorrow? We always call it

let's outline your business objectives, and maybe focus in on your top two or three, we identify what their current state of environment is today. We map out what that future or desired state looks like tomorrow. And of course we assign metrics to that so we can both mutually be on the same path to what that gets to. But, one thing that we really are conscious of is that the right technology stack can make such a significant impact to a mid-sized business.

because it helps with the competitive advantage. And if they're going to compete against larger organizations that might have a plethora of resources, they've got to be small, they've got to be nimble, and they've got to be agile. And sometimes it's first mover to market can win. And for example,

if you got to use DocuSign and I had to send my customer a contract that they had to sign in pen, you would have a competitive advantage, right? Because your customer, made it easy for them to, sign the contract or, and get that paper. So I always look at when we're looking at mid-sized businesses, what are some of the small things that we can help with that can make a bigger impact and what type of

cost reduction can we introduce to their technology stack so that they can be more flexible? Maybe it's a cloud based solution or it's a, we can refurbish old equipment or old technology and repurpose it elsewhere so that they're not, stuck to legacy outdated equipment, right? And just, but we always look for companies that, really I think at least for our part, and I don't just mean at Zoom, I just mean, in other organizations I've been at is,

We do really prioritize the personal touch with those mid-sized companies. I think they're more fun to deal with. You're not just dealing with a vendor. They actually truly look at you as a partner. I feel that they're a bit more open with you because they feel that if they can share more about their business, you're in a better position to help them succeed. And sometimes if you're selling into enterprise organizations, one, you're just a vendor, you're not a partner. It's price only and that's what it is. And you're going up against people that

Jason (08:16)
think that's a great way to look at it.

Mike Hayes (08:26)
won't give you the time of day. Well, I think mid-sized companies, you get to sit down with, whether it's the executive team, whether it's decision makers or the economic buyer, or maybe the founders of the organization themselves, and just learn more about their business. And the best way to earn trust too, is not to sell them anything. There's been many times where I say, I don't think we have the right solution for you based on your company needs. I just, I think we can help you in category A, but we cannot help you in category, you know, A, B and C.

And I think there are better one size fits all solutions that could be more applicable to your business. So you just have to be honest with them.

Jason (08:59)
Yeah, I love that and it actually leads me into my next question because this you just gave an example of it is I think you're one of the best consultative selling executives that I've ever met and and because of that center of gravity that you just shared So how are you? Looking at the qualities like if you're evaluating different salespeople

that you may have on your team or you're competing against. What do you think are the great qualities that make up a super successful salesperson? And I'll do a follow-up, is are there clear do's and don'ts that you would say that they follow?

Mike Hayes (09:34)
every time I hear this question, I revert back to a conversation I had with my great uncle and he was successful in business and had a few businesses and had done very well. And as I had started my leadership journey years ago, I had talked to him about it. We were at a family party and we were just talking about hiring people and he asked the question, like, what do you look for? And one thing that he just rang true, he goes, Mike, you're going to find, don't look at so much the experience. Look at the attributes that you cannot train.

For example, I'm selling Zoom and I'm selling technology just because someone came from maybe a sports marketing background or maybe they didn't come out of undergrad with the right degree, that doesn't mean that you can't train them. He's like, but you can't train integrity, you cannot train honesty, you can't train somebody at this point in their career because they're already wired the way they're wired to be a self-starter, right? By the time someone's say mid-20s or 30s or 40s, you can't train them to be a self-starter and have that self drive.

not to sound cliche at all, but I do feel that you've got to look at the attributes that you can't train. I have brought some really amazing people onto my team. I'm thinking of one, you know, individually right now. He's been here for about four years. He was certainly not the most skilled or the most experienced of all the candidates I was interviewing in, but his attitude was amazing. He was a self-starter. Everyone that had met with him, we kind of put him through a panel of interviews. The feedback was consistent. Like this person is just exudes positive.

know, attitude and he just exudes energy and he has been amazing. I mean, he is now a team leader. He's in a role to, to take his career to the next level from a management perspective, if he so chooses. So I always look for those attributes that I, can't train and sometimes it's hard to do in an interview, right? That's, I try to meet with people as many, you know, as often as I can, if in person, ideal, that would be amazing. But in today's world of remote workforce and hiring on a,

domestic and sometimes even at a global level, a lot of it's done over the phone. You'd asked about some of the do's and the don'ts. I think that when it comes to do's, always think of sellers, you're supposed to listen more than you talk, right? And many times we find ourselves trying to fill the oxygen in the air and we over talk and just listen, ask open-ended questions, learn more about their business. It's something that I call the three E's, right? So it's engage,

educate and empower. if you can engage with your clients, and I mean in a sincere, honest way and you're engaging with them, you're asking the right questions, and then you can bring some value to the conversation and educate them on industry trends and you can educate them on maybe other use cases that similar customers and maybe similar industries have done and what have they learned along the way, and then you can empower them. Once they feel empowered,

Jason (11:49)
Engage, educate, and empower. I like that.

Mike Hayes (12:15)
man, that's a really powerful feeling for that individual or for that company to feel that they've learned something from you and now they can go do it themselves. That's to me, think that's where the magic happens. And as far as some of the don'ts, don't have assumptions. Don't go into any of these calls with assumptions because, what industry they're in. You think you have all the answers or you did a personal profile and you think you know this person and you know how to sell to this person. I would just.

Don't talk too much, don't have assumptions, and honestly, just be genuine with your questions. Don't ask the stereotypical, here's your 10 profiling questions, and here's how you run discovery. Learn more about the business. It is amazing what you can learn from people by just asking some really great open-ended questions.

Jason (12:58)
I think that's terrific. I think there's probably a fine line also between knowing enough about that business and that person and that industry, but also not going in with those assumptions, right? So being knowledgeable, but also being flexible,

Mike Hayes (13:15)
And to that point, think it shows a lot to that customer that you've taken the time to learn their business and learn their industry so that you just go in blind, right? Say, hey, you know what? Hey, I don't know everything, but what I did do is I did do some homework on your industry, or here's my experience in your industry over the last five, 10, 15, 20 years, and here's what I know about your business. I certainly don't know everything. I still have a lot to learn. I just didn't want you to think I came in here blind.

And just the honesty of that sometimes to the customer says, hey, you've at least taken time. And I realize you didn't do that 30 minutes before this meeting. I can tell you've done that over X period of time. And it was a bit more thoughtful than just a quick AI search 20 minutes before my meeting.

Jason (13:54)
yep. And I think, there's a term that sometimes gets in the way, probably with less consultative salespeople, which is ego, right? To kind of show that you're the smartest person in the room and you're gonna sell them. And sometimes it works and sometimes it doesn't.

Mike Hayes (14:08)
Yeah, you've got to put your ego aside. I am a firm believer of that, put your ego aside. I think humility is probably one of the most underrated yet most powerful attributes in business today. And they always say that, I had heard something years ago and it was like, customers are like dogs and children where they can smell.

fear and they can smell, right? mean, Customers can smell BS too, right? And, and so I always think of it this way is, is, you know, don't try to fool the customer. The customer is smarter than you think. They've done their homework as well. And you really have to respect that. and if you don't know anything, it's okay to say, I don't know.

Jason (14:28)
Thank

Mike Hayes (14:45)
Right? Because really the next best answer is always, I don't know, but I'm going to go find out. And as long as you can just, provide the right answers when you have them and be honest with what you don't know. But if you say you're going to go find out, then that's why the follow-up is equally as important as that meeting itself.

Jason (15:00)
And that's how you build lasting relationships, right? It's, it's different than just being very transactional and selling one thing. But if you want to build a lasting relationship with someone, it's that honesty, that openness, that ability to say, let me find out. Cause I don't have the answer for you right now, but I want to make sure you have what you need. That's great. So, as we're going down this path with midsize businesses, midsize clients,

Mike Hayes (15:03)
Thank you.

Exactly. 100%.

Jason (15:24)
What do you see as some of the major pain points during the sales cycle and how do you solve them? And if you have an example, that you could share of a situation where you've identified that pain point and you've solved it.

Mike Hayes (15:38)
Yeah, I think one of the pain points that I have or that I often see with mid-sized companies is, know, IT leaders come into organizations, they don't have all the resources that we had talked about earlier, maybe they don't have this budget, and they inherit legacy equipment. And they're like, man, we've made these capital investments in this legacy equipment, we can't just get rid of it. But then you got to start to really kind of look at it as, okay, you don't have as many resources as you would like.

how can we bring some of that into the cloud? So therefore you're not managing on-site hardware that's going to only get outdated. So I think of the lack of resources, a smaller budget and inheriting old equipment. And I'll give you an example. This is true story. we dealt with a company years ago and they were a company down in Texas and we met with them and the chief information officer, of technology.

had just gotten to the company maybe 60 or 90 days before. He was relatively new. And we're talking about how are we trying to take, they were using six to seven different applications and how they communicate. and we had talked about just consolidating all forms of application into one single environment. And we talked to him about,

well, what does your communication bills look like today? And it kind of opened up Pandora's box and he said, know, team, let me get back down this one. I just got to the organization and about two weeks later, he called us into another meeting and we do a meeting this time that was virtually. And he said, I just want to say thank you. One, thanks for asking the question because it forced me to go back and look at what we had. And what they realized is that they were still paying $7,000 a month in pager bills.

and they have not had a pager in the company in over 10 years. Think about that. And it was just, and he said, I'm embarrassed to admit that, but it just goes to show you that sometimes we're in a smaller company and these contracts were signed by predecessors that were no longer there. And other people in the organization didn't know anything about what contracts were signed, they were lost or maybe filed away. They didn't know anything about technology and nobody was asking those questions. just the mirror.

question of learning more about their business and what are their what's their environment look like today and maybe what's their what's their contracts look like today helped him save roughly eighty five eighty four eighty five thousand dollars a year over ten years so they immediately canceled those contracts and it just led to a great conversation it led to him really trusting us because we went into it with

what else can we help you with as opposed to what else can we sell you?

Jason (18:00)
Mm-hmm.

Exactly. And that's the whole point, right? It's like, to what you said earlier, I'm to be very honest with you. I can do this for you, and I can't do this for you. And that builds that level of trust. So totally agree. We're on our last question, my friend. We've gone pretty far, pretty fast. But we always talk about AI. I think that's how you pronounce it is AI.

Mike Hayes (18:04)
Yeah.

Exactly.

Alright

Jason (18:23)
And when we're talking about mid-sized businesses, you my belief is to what you said about technology, that AI at this stage for mid-sized businesses, it's actually better to be small than large because I feel like these larger enterprises are going to have a hard time trying to figure out for all of the people, the systems, the technologies, the devices that are there. How do I start to unravel every, all the infrastructure that's been built around it? So I feel like.

Some of these smaller companies can move faster than the larger ones, but I'm curious as it relates to a sales strategy. So how do you use AI today as part of your sales strategy, your sales approach, and where do you see it moving in the future?

Mike Hayes (19:04)
Great question on where it's moving as far as how we use it today. I think it should be a crawl walk run strategy. And what I mean by that is that you don't just learn AI overnight. It's not like, took a class and all of a I get it. I think that you've got to just be open to it. Try it, right? And try all different forms of it, whether it's, and I don't just mean ChatGPT and Grok and Gemini and we've got Zoom AI and I'm sure there's Microsoft Copilot, which you've got to pay for.

I'll just give an example. Zoom has AI companion embedded into our platform at no additional charge. Right. So it's just if you have a paid version of Zoom, you are entitled to AI companion. I use it extensively. If I'm walking into a meeting, I will actually there's a toolbar that says,

Can you tell me what this meeting will be about? And it looks at all my previous meetings with the same participants and it says, well, you've met three times with these previous people. Here were the four action items. And by the way, here's the two that you were responsible for. Now I know what I have going into it. So that I can prep for the meeting ahead of time. If I'm meeting with external people, can provide me with their profiles and said, Mike, you're about to meet with, you know, Jason. Here's Jason's profile. Here's his past experiences.

Here's a summary of the past emails and maybe meetings you had with Jason. Because sometimes these meetings might have been a month ago or maybe two months ago, depending on what type of nurture campaign you're talking with these folks.

Now, we also have access to all the transcripts and I get a summary after all of my meetings. I take that summary though and I can throw it back into AI and say, well, okay, I wanted to build a table. I can say, build out a joint engagement plan that talks about

agreed upon business objectives, talked about the pain points that we discussed on the call, talked about the impact that these solutions are gonna make to the business, and please outline all the sequence of events that we will need to make this a successful journey with the client and assign ownership. So it can build out all that for us because now what you've just proven to the client is you've done this before, right? I mean, this is why big...

consulting firms in McKinsey and Bain and Deloitte do such a great job because they've done the same thing countless times and they're using best practices to guide the customer through exactly the framework, the structure. Here's how you do it. And if we can put together a joint engagement plan we've just earned credibility. They like roadmap, they like structure, they like guidance.

And we've given them a timetable. It also helps us keep both sides in line. So for example, a month goes by and the customer missed some of their action items or the engagement plan. It gives us the opportunity to go back and say, hey, Jason, we had this joint engagement plan. It was all predicated on these business objectives. I'm thinking that maybe some of these business objectives have changed based on we're missing timelines. ⁓ I'm so sorry. You know what?

Jason (21:41)
Mm-hmm.

Mike Hayes (21:44)
We've had a merger come up that wasn't expected, that kind of great. Let's talk about that. But I think, you AI has also given me the ability to, for example, we have AI built into our phone system. So if I get a voicemail and it's just a standard voicemail, that's great. But if I get a voicemail that was high priority, someone sounded urgent. said, Mike, I need you to call me immediately. That goes right to the top of my voicemail box with an asterisk next to it. And it gives me the email outlook to it. So I know exactly.

I need to attend to that one faster. And in sales, if a customer is having an issue, you need to attend that to a lot faster than somebody else is randomly giving you a call. I try to use AI for all attributes of my business, pre-meeting, in-meeting, post-meeting, but really how do I make it a better customer experience for my partner or for my client?

Jason (22:30)
That's what you had mentioned about the voicemail. That's really interesting. didn't know that existed where it's listening to the tone or the cadence and identifying that there's a different priority

Mike Hayes (22:40)
Absolutely, and it's been a big help right and thankfully I don't have to use it all that much But when it does I just had to use one last week I was traveling and as soon as I got off an airplane I came back and it had notified me that I had three voicemails But I knew exactly which one I had to call back first

Jason (22:54)
That's and I was your wife. Well, we finished our five questions you passed with flying colors. So thank you for that. I do have a bonus question that I ask all of our guests, our advisors, which is as an amazing advisor on The Wisory and thank you for making time and sharing insights. What should our midsize business leaders or executives come to you?

Mike Hayes (22:56)
Exactly. kids asking for more money.

Jason (23:21)
to help them solve.

Mike Hayes (23:22)
That's a great question.

I think that any IT leader, big or small, but specifically for mid-sized companies, you're not in this alone. if you're working with the right consultant, trusted advisor, I'll call them, get their feedback. Right? We live and breathe this every day.

We have seen all the hiccups from other customers in the pitfalls and in the traps that other clients have made. And we can share those best practices.

I love technology and I try to keep my mind fresh and stimulated all the time with technology way outside of anything that I sell.

But I think it's just going to these conversations open minded and realize that from a midsize company, you don't have a huge team. It's not a ⁓ one person job, right? Reach out and realize that it takes a village.

to be successful. So I think just be open-minded and ask good questions.

Jason (24:08)
I think that's great. would it be okay if a mid-sized business wanted to reach out and say, hey, I'm starting to build a sales team or I'm starting to reconfigure the way that we go to market. Can I pick your brain in terms of the types of people, the types of qualities, the types of skill sets that I should be looking for within that team?

Mike Hayes (24:25)
100 % Jason, I am more than happy to give any feedback, insights, suggestion, advice, whatever that may be. I've worked for, like I said, I've worked for, you know, 12 person startups out of Silicon Valley and I've worked for fortune 50 companies with, 300,000 employees. So I'd certainly prefer the smaller size because that way I feel, I actually feel I can make more of an impact. But I guess where I'm going with that is I'd be more than happy to give.

know, feedback or advice on the experience that I've been really fortunate to have over the years. And if I can help anyone, build out a sales team or choose the right solutions or just, you know, answer some of their questions, I'd count me in on 100%.

Jason (25:01)
I love that. So Mike, thank you for that. And I'm so honored that you're a part of The Wisory. I just want to thank you for taking the time to answer our five questions and be an amazing advisor on The Wisory. I will talk with you soon, my friend.

Mike Hayes (25:16)
Sounds good. Jason, I appreciate you and everything that The Wisory has brought to the table. I I feel honored and fortunate to be part of it. Certainly learned a lot with discussions I've had with you and I look forward to being more engaged.

Jason (25:26)
Very kind of you. Back at you. Thanks again, my friend.

Mike Hayes (25:28)
Thanks, Jason.