MKJ (00:01.292)

Hey, hey, CEO Mischief Makers, welcome to the conversation with someone I am just like jumping out of my skin to be able to talk to and introduce you to if you don’t know her already, Ashley Gross gets to join me on the conversation today. Hey Ashley, you ready to rock?

Ashley Gross (00:15.938)

I am.

MKJ (00:17.45)

Okay. All right. So everybody just a little bit of a background on how I met Ashley. And I’m telling you these conversations, these relationships can develop if you align with someone and you’re just unique and you and genuine, you have no idea where things can go. So Ashley and I met in Mark Schafer’s community. She was doing a presentation to Mark Schafer’s community of which I am a member.

And it was like, my gosh, I have to talk to this person. So we connected and we’ve had a conversation and it’s like, we’ve got to talk on the podcast. So thank you for joining me. I’m so happy we’re here together. let’s dive into mindset. That’s what this is about. So you have such a unique trajectory in what you’ve done over the last, four years. what in the world, first off, tell people who you are and what you do.

And then secondly, start off with this whole mindset shift that you had that got you into doing what you’re doing right now. So I know that’s a complicated question, but start off with letting them know who you are.

Ashley Gross (01:18.167)

Yes.

Ashley Gross (01:21.834)

No, I love this question. Okay, so let me go back a couple of years. So obviously my name is Ashley Gross. Before I was all these wonderful things that I’m about to spout off, I was a 10 -year marketer. And in 2020, I found out I was expecting my son. And I was really, really excited for this. I didn’t know much about kids, obviously, because this is our first, but I knew I wasn’t going to have a lot of time on my hands. And I’m a firm believer that the…

future of working is going to be based on outcome and not based on hourly. So instead of using your time and getting charged per time, you’re going to get charged per outcome. So it was kind of like this moment for me of clarity where I was like, gosh, I’m about to have way less time on my hands, and I need to figure out how to still complete 40 hours worth of work in 15 hours, right? Because I a recession -proofed my job, and I knew I was going to be a mom. And so I started dabbling around in Jasper AI.

And I really used it to streamline everything. Instead of just working for the sake of working, I built a strategy, right? Like why am I creating content? What am I doing? And I trickled it down. And long story short, I developed so many use cases, but I was able to condense my work week from 40 hours to 15. And then flash forward to 2022. And because I was using AI for everything and had an AI first approach, I garnered the attention of the CMO. And she was like, hey, listen, you’re already known as the AI girl internally.

is there any way that you kind of want to roll out AI? We don’t know what we’re doing, but we want to figure this out. And I was like, yeah, absolutely. Because coming from a marketing background, my trajectory originally was just CMO. I feel like that’s how a lot of marketers are. It’s like the end goal is CMO. And so with this realization of, my gosh, AI is wild and disruptive and chaotic, I was also like, this is a good visibility moment for me to raise my hand.

And instead of waiting another five to seven years to work my way up to CMO, why don’t I just raise my hand and see where this goes? Because maybe I don’t want to be a CMO. Maybe I want to change verticals or something. And so I raised my hand. And I did this on top of my marketing job for a year and a half. And long story short, we developed 25 use cases, over 25 use cases. And they are all so cool. And I would love to nerd out over them. But.

Ashley Gross (03:33.45)

I know that the real measurement of success was we overachieved our pipeline target of 90 million and hit 115 million three months after implementing AI. So talk about like a bananas experience. I went from being an individual user and contributor to training over a hundred people on how to use AI effectively and productively. And I was able to measure and tie that impact into revenue, which is like kind of crazy, right? All pre -taught GPT.

And having that experience, was like, holy crap, like this is wild. This is really going to change lives. And immediately I was like, know, enterprises, just the bigger a business gets, the slower they are to innovate because there’s more people. And so my first thought was, this needs to be in the hands of small business owners, solopreneurs, smaller companies in general, because they can just rapidly innovate faster anyways. So AI is only going to enhance every single thing that they’re doing. So I went on to create my own company.

MKJ (04:26.402)

Yeah.

Ashley Gross (04:28.85)

and founded a community where we don’t just educate and upscale employees, we upscale employers so that we can actually align the workforce and see real progress happen with AI. And it’s so cool and it’s the wildest experience ever and I’m just so grateful for everything. But it really just started with me saying yes and raising my hand and not knowing what the heck I was doing, but being determined that I was gonna figure it out.

MKJ (04:52.524)

my gosh. it was you, kind of became a, from what I hear you saying, you kind of became a accidental AI user because you looked around and realized, okay, I’ve got this job. I still need to make the same amount of money, but I also have the son and I’ve still got to want to be a mom. So I’ve got to figure out a way to do both of those things and spend less time in my job, but still do the same job and be able to spend more time as a mom. So it’s kind of like an accent. You looked around for tools that would allow you to do that.

Ashley Gross (04:59.964)

Yeah.

Ashley Gross (05:15.443)

Yes.

exactly.

MKJ (05:21.55)

that will enable you to do that? What made you do that? Because most other people, we all have become, I’ve become a mom, I did it differently from what you did, but it was the same concept, the same process, the same thought process. But most of us either make the choice, the decision. I’m just gonna either quit my job or go down to part -time, or I’m gonna put my kid in daycare and just leave it at that and stay full -time 40 hours, or any combination of those two.

Ashley Gross (05:22.003)

Yes.

MKJ (05:49.452)

We don’t usually look around, very few people look around and go, what tools do I have at my disposal to be able to do both effectively, but spend less time over here? What the flip made you in your mindset decide I’m going to look for tools to do this?

Ashley Gross (06:05.994)

I think the mindset shift really happened back in 2020 when I realized I wasn’t getting a maternity leave. Talk about a naive first parent. I very much thought that the company I worked for, they loved me. They had actually just given me a bonus. And they had intentionally told me that I got the biggest bonus out of the whole entire company. And so I was like, this is going to be easy. I’m just going to say I’m pregnant. these things are going to happen. And again, looking back, I just kind of want to give that version of myself a hug because bless her heart, what if she didn’t know anything?

But when I had to go back to work two weeks after giving birth to my son, that was really the moment where I was like, no, we’re not doing this. This is not, it wasn’t, you I knew that I needed a plan and I knew I needed to be intentional and strategic. And so the moment that I found out I wasn’t gonna have a maternity leave, it was really like, okay, the problem is I need to figure out how to work 40 hours worth of work into 15 hours and still have a good outcome, right?

I knew the problem, and so finding tools that were built to solve problems around productivity, it was like, OK, we diagnosed this, we’re vetting these tools, now it’s experimentation. And so it’s really just a formula of, found this problem, what are the tools that are saying they can solve this? Are they safe to use? Do we know what they’re doing with our data? Let’s go experiment if all those things are a check mark.

MKJ (07:29.314)

Yeah, yeah, that and that I think it from what I hear you saying again, it kind of comes from the way you look at marketing and your marketing position is that very logical strategic way is a problem that’s out in the world. And we can do this from a marketing standpoint. These are our customers. This is the problem they have. Then here’s our solution. This is how that will solve it. And then now it’s a matter of being aware and testing the waters and getting as many people to be aware of it as possible. So you just took that same framework and applied it to your specific position.

Ashley Gross (07:59.379)

Exactly.

MKJ (07:59.67)

Wow. Yes. So now let’s go further. So yes, you said yes. And, and I’m telling you, mischief makers listening, when you’re given an opportunity like this, I mean, it’s so rare to begin with, to be given an opportunity like you, you had, why would you say no? Right? How could you, I, I had this situation when we were, we went to Europe for the first time, we went to Norway and, you know, they’re like, you’re from California. You have a Tesla. We’re like, no.

And they’re like, well, would you like to rent a Tesla? And I’m like, yes. And my husband’s over going, well, I don’t know. It’s kind like, dude, stop. No, we’re renting a Tesla. I don’t care what we have to do. If it’s only like another five bucks a day, are you kidding me? Why would we not? Right. So it’s that kind of situation. But this is way bigger. You had this opportunity from the CMO because you used it in your own situation without any expectations.

Ashley Gross (08:38.452)

You’re like, no.

MKJ (08:57.826)

from the company and first off I cannot believe I at least got six weeks in disability when I delivered my kids it’s down to two weeks now what the what.

Ashley Gross (09:05.333)

Yeah. And it wasn’t even two weeks. I had to use my vacation time. So it was one of those weird, it was a weird rule. And I fully don’t understand it still. I just kind of like moved on. But it was one of those things where you had to work for the company for nine months before you announced you were pregnant in order to get the maternity. It was very, very strange. But yes, I went back to work two weeks after and I had to use my unpaid vacation hours to take off.

MKJ (09:32.554)

Okay, that’s nuts. I’m not even going to touch that. I’m not going to ask you what company that is. I’m just going to go move past that because that really pisses me off. But anyway, all right. So now you did this out of your own necessity with no, no expectation from the company at all, because it was on you to figure this out and you did it. And then how did you get the attention of the CMO? What, what happened in this process to go from, I’m doing this by myself in my own little world over here.

and then the CMO says, hey, roll it out. I mean, that doesn’t just happen the next day.

Ashley Gross (10:05.564)

No, it happened over the course of, think, probably seven months of me just sharing knowledge. I’m really, really big on once you have knowledge, not gatekeeping it. And so any time I had the chance to network, I would always incorporate AI into the conversation, because who doesn’t want to get rid of the monotonous work that they hate doing? Everybody has something about their job that they have to do that they hate doing. And so I almost looked at it as a networking liaison for me.

So whenever, I’m sure everyone to a certain degree feels like this, when you’re trying to network with senior executives, it can be really nerve wracking, especially when you’re remote, because you don’t know how their vibe is or how to, you don’t know anything intimately about them. And so anytime I was on a call, I would just intentionally say, hey, I saw that you’re preparing for that board meeting next week. Are you using any AI tools to streamline that? Because that’s a pain point that I knew that they had, and I knew like,

time wise, it takes hours. And I mean, you’ve worked for many companies. I’m sure you know the moment like there’s a board meeting scheduled, every single employee doesn’t matter who you are. They’re like, God, our executives are going to come to us and ask for a million things that day. So let’s just prepare to have our work done for that day so we can be on call for our executives, you know? So it’s really just finding those painful pain points that are just painful enough that they’re willing to be open and vulnerable to any suggestions for improvement.

MKJ (11:10.304)

Here we go.

MKJ (11:27.384)

Yeah, wow. And so you took the initiative to reach out and say, hey, are there any of these things that I could help you with? And then they were like, sure, that would be great. And then you basically educated them on how to do that. And obviously they got an immediate benefit, immediate ROI in the sense of their time less and their output higher. So then you just kept doing that for different executives or did you specifically just do it for your CMO?

Ashley Gross (11:35.305)

Yes.

Yes. Yes.

Ashley Gross (11:50.388)

Yes.

Ashley Gross (11:56.244)

So I did it. I know I didn’t actually do anything for the CMO. She heard from a couple senior executives. So I wanted a promotion. And I knew I wanted a promotion. And so I was like, OK, who are some people that are not in marketing that can be my internal stakeholders? And so I was very intentional. So I went to the head of product. I went to the head of sales. I went to a couple members of the HR and people teams. I strategically picked a few from each department, though.

And I already knew what use case I wanted to pitch to them for AI, but I made it organically come up in conversation. So I would book time with them and I would say, hey, like I’m demoing this AI tool. Do you have any use cases where you really hate doing something? And then, you know, most of the time they would say the task that I already selected, because I did a little bit of research beforehand. But if they didn’t have any ideas, then I would say, perhaps. And I would like cherry pick the one I already thought. And they were like, of course, that’s a great idea. So it’s really just like how you intentionally network.

but apply AI to that. It was really just a copy and paste formula that I used.

MKJ (13:00.182)

And so then once you were doing that with other senior executives then because the CMO was you know in that in that hierarchy did did he or she just start getting wind of it or did you did it was there an intention to trying to get the senior executives to go to bat for you I mean how did how did that go.

Ashley Gross (13:20.522)

Yeah, so on top of having intentional conversations with these other senior executives in other departments, I asked her if she would mentor me. And again, this was very strategic and intentional. And so I said, 15 minutes every other week, I will have the outline ready to go and the questions. And so I aligned this with our all hands calls. So every time her and I had a mentorship session, it was after an all hands call when we had a company update about priorities, what was going on. So I knew that I didn’t have to guess where her mindset was.

and what her priorities were because I had just heard it in a call. So I didn’t have to ask her a bunch of questions. She didn’t have to repeat herself. I did all of the work, right? And so she kind of really just said, listen, the board is coming to me and asking me to roll out AI under the realm of digital transformation because CMOs get stuck with these things all the time. And they’re really ambiguous as usual. And I was like, yeah, this is great. We don’t have any set expectations for this.

Let’s go at this with overall job satisfaction and let’s try to add more job satisfaction to every employee’s workflow because if the employees are happier, then they’re going to get better customer service, our brand excels. And so my mindset was I’m not going to tackle this from a aspect or perspective because a lot of people aren’t aware of how much time they’re spending. So my mindset was really let’s make everyone happier. And in the back of my mind, I was like, OK, if I make the employees happier,

MKJ (14:27.086)

Right. Right.

Ashley Gross (14:45.012)

from an executive and board level, they won’t have to lay people off. We ideally won’t have employee turnover. We’ll be able to upsell and cross -sell more. We’ll be generating more sales. So I kind of was doing these mental jumping jacks on front end Ashley, back end Ashley. And I knew back end Ashley was the board. But what I presented to the rest of the employees was job satisfaction. It was very intentional, though.

MKJ (15:08.494)

Yeah, that and so that when I talk about mindset, so many of the mindset shifts I’ve had have been accidental, have been where I did something and accidentally I got a result and I went, I can do this. This kind of a mindset, you are very intentional, you are very strategic. And it’s not just strategic, I completely do not get the vibe from you.

Ashley Gross (15:28.596)

Mm

MKJ (15:36.322)

that you have a hidden agenda and you want to make your pie bigger, your pie slice big. That’s not the intention. The intention is that this is a way the world can be better. And right now, my world, weren’t, I know, thinking about your own business or anything like that, right? This was just my intention is to get to CMO. And the way I make my world better is employees and employer and board make all of that better.

and talk to the person I’m talking to not because I’m trying to manipulate but because I know their position so when I’m talking to employees I’m going to come from the mindset of the employees when I’m talking to senior executives I’m going to come from mindset of senior executives and then they will then take it to the board. Unless you actually got the opportunity to talk to the board that’s it that’s a totally different thing did you. Wow.

Ashley Gross (16:04.51)

Yes.

Ashley Gross (16:20.714)

Exactly.

Ashley Gross (16:26.044)

I did. again, so I, it’s funny because when you listen to your gut, you know, you, and we talked about this before this podcast episode, but when you listen to your gut, your gut says yes, but then at a certain point you have to start saying no to things. And so one of my, the CMO was like, Hey, you know, here’s your learning and development budget for this. If you want to go to any conferences, like you can use this budget however you want. Maycon was right around the corner. This was two years ago.

MKJ (16:40.675)

Yes.

Ashley Gross (16:54.324)

And I was like, OK, well, I want to go to Maycon. And she was like, OK, great. Our board members are going to be there as well. So if you want to meet anyone, let me know. And I was like, yeah, absolutely, I want to meet the board members. And so again, this was really intentional. I could have used this learning development budget however I wanted. I personally am not a huge fan of in -person, because I have a hard time compartmentalizing and learning and networking. But again, I was like, if I want them to know the impact and I want to get better at what I’m doing, because I’ve never been a board member, I need to communicate with them.

Went to Maycon, before I went to Maycon, I reached out to this board member and I said, would love to meet up. So I already had a dinner on the books with him and his staff. And I was explaining my background and where I came from. And again, that was intentional and that led to more opportunities. So it’s a portfolio company and they own multiple other companies. And so they put me in contact with their other portfolio companies when they were getting ready to roll out AI.

to kind of use me as this point of contact and reference of like, well, why did you pick this vendor? And what about this? And what was this conversation? So again, just like leveling up, because it’s like, once you have the foundational skills and you know how to use these tools, then it’s time to teach, right? If you’re not learning, you should be teaching ideally both. And then it’s like, OK, roll this out to 100 people in the organization. Don’t have board experience. All I have is executive experience. Let’s level up again. And you keep going. And I really think my mindset has always been, I never want to be an expert.

Because that means that I’m throwing in the towel and I learned everything I needed to. And that is terrifying to me. It really is. I think there’s always room for improvement. that’s really been a big mindset shift for me, is just continuing to, if I’m interested and there’s passion there, we can keep digging in. We can always go deeper. If there’s not passion, then it’s time to switch careers. It’s time to try something differently.

MKJ (18:25.122)

Yes. Yeah.