IAM2083 – CEO and Marketing Expert Helps Brands Develop Go-To-Market Strategies

In this episodes, we have Amy Winner, CEO of Wheels UP Collective and a marketing expert with 25 years of experience helping brands navigate uncertainty and develop go-to-market strategies.

Amy Winner shares the benefits of intentional thinking in marketing and ensuring successful investments.

The conversation highlights of learning and understanding the subject matter, particularly in the tech industry to be a better marketer and connect with customer. Emphasizing creating an environment where employees can do their best work, empowering and inspiring them, and removing obstacles.

Website: Wheels Up Collective
LinkedIn: Amy Winner

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Transcription:

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Amy Winner Teaser 00:00

The first question I love to ask CEOs is, like, what keeps you up at night? What is keeping you wide awake worrying about, and then how can we use marketing to help fix that? Because, again, back to what I said before, like, marketing used to be in this little bubble, and now we can help every single department in the organization some way or another.

Intro 00:20

Are you ready to hear business stories and learn effective ways to build relationships, generate sales, and level up your business from awesome CEOs, entrepreneurs, and founders without listening to a long, long, long interview? If so, you've come to the right place. Gresh values your time and is ready to share with you the valuable info you're in search of. This is the I AM CEO Podcast.

Gresham Harkless 00:47

Hello. Hello. Hello. This is Gresh from the I AM CEO Podcast, and I have a very special guest on the show today. I have Amy Winner. Amy, excited to have you on the show.

Amy Winner 00:55

Great to be here. Thanks so much for the invite.

Gresham Harkless 00:58

Yes. Like, super excited to have you on and talk about all the awesome things that you're doing. But, of course, before we do that, I want to read a little bit more about Amy so you can hear about some of those awesome things. And Amy has spent the last twenty five years helping brands turn uncertainty into opportunity. Whether recession, competitive pressures, market changes, or COVID19, Amy has worked alongside both B2B and B2C leadership in a variety of industries to build a pragmatic and resilient go to market strategies while navigating change.

She's built multiple in-house marketing teams at early stage tech startups and led them through successful acquisition and now helps high growth B2B SaaS companies grow as the CEO of Wheels Up Collective, a boutique marketing agency. Her absolute favorite thing to do is to hop on a call and brainstorm with new entrepreneurs and CEOs about how to identify and leverage opportunities that can help their companies grow.

And before we were sent to do this recording, I was reading a little bit more about Amy. Amy is a former D1 athlete, National Champion as a Collegiate Rower, and also is a competitive Equestrian as well too. And I was listening to one of her interviews, and I think she said her first job was as a horse groomer business at the age of twelve. And we had a great conversation when we first connected, so I appreciate her journey and her willingness to share her journey as well too. So excited to have you on the show, Amy. Are you ready to speak to the I AM CEO Community?

Amy Winner 02:19

Yeah. I really hope I don't become known as the 12-year old horse groomer. Like, I need to redeem this out. Camping my claim to fame.

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Gresham Harkless 02:27

Hey. So there you go. It's such a cool story, but, I feel like you've done a lot more since then as well. So we'll just add that as an antidote in addition to everything else you've been doing, right? If that works. Alright. Let's rewind the clock a little bit more on how you got started wanna call your CEO story?

Amy Winner 02:43

Yeah. So I as you mentioned, I've been in Marketing for 25 years and mostly in small companies or startups that were really trying to figure out how to get our footing quickly, whether it was, like, a new product roll-out, whether it was an acquisition, whether it was a new competitor, trying to break into a new use case, new personas. That's like my jam is figuring out how to make it work when you don't know how it's gonna work. And took a slight detour and ended up at a huge ginormous corporation, and just it was a terrible fit. Like, I just, it was slow moving. It was political. It just was and this was in 2018 and 2019.

And so in December of 2019, I quit. I quit and was gonna just take some time off and figure out what I wanted to do, and then COVID hit. And I was talking to one of my good friends, and she had gone through a very similar situation. And we were both getting hit up. We forget in the early days of COVID, like, there was a scramble to digital. There was a scramble to get online and be able to reach an audience online and talk to an audience online. And so both of us were getting hit up for by past colleagues. Can you help us? Can you work on this? Do you want a side hustle? And so, I don't know, we just start talking and the next thing you know, we're starting a digital agency. Everybody else is baking sourdough bread and we're like, let's start a marketing company. Not really thinking it was gonna be a thing long term, but four years later, here we are and growing faster than ever.

And so it's been it I always joke when we meet with our early entrepreneur owners and CEOs, no one starts a company because they wanna send marketing materials or write emails. Nobody starts a company because they wanna learn how to do payroll. So it's definitely been a lot of that learning for me to figure out, okay, I know the marketing part of it, but I was bored with that and was looking for a new challenge. And so the entrepreneurship of running a company and hiring people and figuring out how to grow has been a a fun sort of second career. So it's been fun. It's been really fun.

Gresham Harkless 04:49

Yeah, absolutely. I love that, especially because you hear so many times, like you mentioned, the sourdough bread entrepreneurs or but there's usually some opportunity that can come about when there's that level of disruption as we all had experienced. And I really enjoy hearing how those innovations ideas sometimes come about, like, during times like that.

Amy Winner 05:14

Yeah, absolutely. Definitely, you look back, and I never thought life would look like it does right now, but I'm happy that it happened the way it did so.

Gresham Harkless 05:23

Yeah, absolutely. So you touched on it a little bit, and I imagine you probably have a lot of these conversations on a daily basis where sometimes people are really great at the things that they do. Those things might be sourdough bread or it might be running a store, a storefront, whatever it might be or combination of those things. But usually, they're not thinking about the marketing piece or what that looks like or all those things. So I imagine that's where you have a lot of those conversations and are able to build that bridge so that whoever's doing those great things, those great products and services and those teams are able to get that out to the world so that they can get those clients to customers.

Amy Winner 05:57

Yeah. And I think, like, marketing has a bad rap from twenty or thirty years ago where it was seen as, like, a black box where you just throw money at it and who knows if it's working or not. And it's not like that anymore. Like, there you can track the efficacy of your marketing spend, and I think there's an opportunity to be really strategic about marketing and use it as a learning tool. We're always trying to figure out, like, how can we run sure. We're gonna run this marketing campaign, but what are the learnings? What are the tests we can run through it?

And we always start with a hypothesis about what we think is the right is the way it's gonna go or we think is what the market the direction the market's going in. And then we really try and use every marketing tactic as a way to test that and to learn from it. And I think that a lot of times, especially in early days or small business days where you have so much on your plate, like, you just don't even have the brain space to think about marketing that way. It's kind of like, oh, I just need to get it done. And so I think that's a little bit of a a twofer that you can get out of that if you take a minute to think about it, like, really intentionally.

Gresham Harkless 07:01

Yeah, absolutely. So I wanted to drill down a little bit more. Could you take us through, like, how you're working with your clients? How you're making that impact and be able to make sure that investment goes well? Could you take us through, like, what those products and services look like?

Amy Winner 07:12

Yeah, absolutely. We are a full stack boutique marketing agency. We're tuned especially for, B2B SaaS companies, and that's only because those sales cycles are fairly consistent. Once you figure them out, they're fairly consistent and formulaic. And so we're pretty good at building that and ramping it quickly. And we're used to we just have a lot of experience working with those kinds of sales organizations. So that's the little, like, niche in the world that we've carved out and stuff our flag in that that piece of land. I spent fifteen years in startups in Seattle, and so know that space. And tend to like the pace and the accountability that it brings. So we can do everything from building a website to running demand gen campaigns to PR to graphic design.

And every single we don't have, like, a standard engagement because everyone's different. Every single company that we work with and by nature of being early stage or dealing with some sort of change, they don't they're all different what they need. And so we end up having a conversation. The first question I love to ask CEOs is, like, what keeps you up at night? What is keeping you wide awake worrying about, and then how can we use marketing to help fix that? Because, again, back to what I said before, like, marketing used to be in this little bubble, and now we can help every single department in the organization some way or another. And so really thinking about growth holistically and figuring out what, programs, whether they're customer facing or internal facing or prospect facing or ecosystem facing, what kind of programs can we run to help drive that growth? They're pretty fun conversations.

Gresham Harkless 08:52

Yeah. Definitely sounds like it. And do you feel like that's part of what I would like to call your secret sauce? It could be for the organization, yourself, or a combination of both, but do you feel like your ability to not just see that, but also execute that and step into those shoes sets you apart and makes you unique?

Amy Winner 09:06

I think that people and this is such a cliche answer, but, like, the people on our team is that's our secret sauce. And I think maybe part of that is everybody thinks about it that way. That I think you're right. That is our one of our common tenants that we organ that we operate under. I think a lot of times, companies are in such a time crunch to hire. Like, you need this you need extra help so badly, and so you just end up hiring anybody. And I think that's such a shortsighted answer. I think that hiring is the most important thing you do in an organization. Whether you're a service organization, whether you're a software company, whether you no matter what kind of company you are, the people that work for you, it's so important.

And I just challenge business owners to hold the bar really high because it ends up taking so much more time to handhold somebody who's maybe not ready for the role or manage somebody who's in trouble or replace them down the road when you hired the wrong person. And even though it gets so painful when you really need to fill that headcount, I think usually it's worth holding out for and really finding, like, the right fit culturally and still skill set and personality, and it's really hard. It's hard to hire people. It's really hard to hire good people.

Gresham Harkless 10:24

Yeah. Absolute so I wanna switch gears a little bit, and I wanted to ask you for what I call a CEO hack. So this could be like an Apple book or even a habit that you have. But what's something that makes you more effective and efficient?

Amy Winner 10:34

Yeah. So this one, it I was thinking a lot about this because you always ask this question on your podcast. But, like, my hack is, like, a to do list hack. And especially as I did not start a marketing agency because I wanted to learn how to do payroll or I wanted to learn QuickBooks or I want I did. And I think that you need to look at your to do list, which is always way too long, right? And I put it I put everything into four different categories. One is, like, something that only I can do. There's no one else in the team that I can outsource it to. Some the second one is something that I would have to learn to be able to do, so looks in that in that case. One of them is, something that I can delegate existing on the team, and the fourth one is, like, something that I actually like to do.

And so I think that especially as maybe this is unique to me. I don't know. I'm like a control freak. I'm like a type a control freak. And my co-founder and I started this company together, and we we're gonna do everything. And you can't, and you need to be able to trust people. And this goes back to where I was saying you gotta hire really good people, and then you gotta delegate to them. You have to be a little scared and give them more than you think maybe they can handle and give them a chance to grow and learn and step up a little bit. But, also, I think I need to push myself constantly. I constantly have this inner dialogue with myself. With, like, is this worth my time to do this? What what's the opportunity cost of me having to learn to use this new software because it's for HR or it's for there's a million things that I could be spending my time on, and is this really the the most important thing? Because I'll tell you my to do list is always, like, a hundred miles miles long.

But I think too, you have to make sure that you there are things that you just like to do that probably you could delegate, but they're like little mental breaks or they're a little they're easy to I who doesn't love check checking something off a to do list? Right? Sometimes maybe it's just me, but I've had the to do list with, like, things that I like to do that are easy, and you feel some sort of accomplishment that you got that one little thing crossed off. So I think being, like, super critical about your to do list and being, like, pretty honest with yourself about what you're good at and what you're not good at and not just getting overwhelmed by a really long to do list is something that you probably have to figure out pretty early on if you're gonna be successful in running a business.

Gresham Harkless 12:48

Yeah. That makes so much sense. So I wanted to ask you now one of my favorite questions, which is the CEO nugget, which if you were to hop into a time machine, what might you tell your younger business self or potentially you might tell your favorite client?

Amy Winner 12:59

If I was gonna tell myself, I we work in tech. We are in I am knee deep in tech, and I wish I had learned the tech more younger in my career. I wish I had prioritized learning the subject matter a little bit better. Like, I can hang with a director of product, but I think I would be a better marketer if I really and I think this this applies to any industry, any leader, really understanding what it is you're selling or your the service that you're providing and really getting as close to the customer as possible and understanding what makes them tick.

Because I think that not only does it help you articulate it better and and find better solutions, but it we it can only lead to empathy, right? Can only and I think the more empathetic we can be in general in life, the better the world is. So see, I'm creating world peace here, where it is just be empathetic people.

Gresham Harkless 13:53

Exactly. Exactly. That's the CEO mountain for sure. So what would you now consider to be your answer to my absolute favorite question, the definition of what it means to be a CEO? And our goal is to have different quote, unquote CEOs on their show. So, Amy, what does being a CEO mean to you?

Amy Winner 14:06

Yeah. And I'm gonna steal this from another CEO that I used to work for, but he said it and I absolutely this is my life goal is I wanna create an environment where the people who work with us can do the best work of their life, the best work of their career. I wanna empower them and inspire them and, like, bust roadblocks out of the way so they come to work and they can do the best work they possibly can. And this goes back to, like, you gotta hire good people, right? You gotta hire good people who wanna do good work most days, the vast majority of days.

But I just I find when I can think about empowering the team, then the rest falls into place. If you hire good people and you empower them and you set them up with growth opportunities and give them work that they wanna do, that they're good at doing, that gives them, advancement opportunities, like, the customers are gonna be happy. Like, that's the easy part, making the customers happy once you do the rest of that. So that's what I challenge myself to do every day. Some days it happens, some days less, but that's my North Star.

Gresham Harkless 15:13

I love that. We truly appreciate that definition, of course. I appreciate your time even more. So what I wanted to do now is pass you the mic, so to speak, just to see if there's anything additional that you can let our readers and listeners know and, of course, how best they can get a hold of you, find about all the awesome things you and your team are working on.

Amy Winner 15:28

Yeah. So you said it in that bio. Honestly, my favorite thing to do is talk to young entrepreneurs early in there, and I try to do one a week. I try to take one call a week from somebody. It's not a sales call. I'm not trying to sell you anything. It's just if you wanna pick my brain. So I encourage anybody out there who wants to have a fresh set of eyes or fresh set of ears to talk through things like, hit me up, send me an email, let's get something on the calendar. I think there's a scheduling link on our website, but I'd love to have those conversations. But you can find us online at wheelsupcollective.com. We're on all the social media channels as well, and we would love to help you grow.

Gresham Harkless 16:05

Awesome. That's awesome. Thank you so much, Amy. Of course, to make it even easier, we'll have the links and information in the show notes as well too, so somebody can take you up on that offer and opportunity. But truly appreciate you for your time, and I hope you have a phenomenal rest of the day.

Amy Winner 16:17

Thanks. You too.

Outro 16:19

Thank you for listening to the I AM CEO Podcast powered by CBNation and Blue16 Media. Tune in next time and visit us at iamceo.co. I AM CEO is not just a phrase. It's a community. Be sure to follow us on social media and subscribe to our podcast on Apple Podcast, Spotify, Google Podcast, and everywhere you listen to podcasts. Subscribe and leave us a five-star rating. This has been the I AM CEO Podcast with Gresham Harkless,Jr. Thank you for listening.

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