Balancing Career Advancement And Family Responsibilities As A Female Leader with Dr. Amy Osmond Cook — The Rainmaker Podcast

Welcome to the Rainmaker Podcast, where we elevate marketing leaders inside and out. I'm your host, Veronica Ramy, master marketer, executive leader, and mentor to marketing leaders wanting to advance their careers. Each episode is filled with genuine, unscripted conversation with some of the world's top marketing experts, leaders, and trailblazers representing brands both big and small. Our goal is simple, to inspire you and provide you with the insights and tools that you can master your role, nurture your team, prioritize your wellbeing, and evolve into an industry-leading Rainmaker. This is the Rainmaker Podcast. Welcome back to the Rainmaker Podcast. In this episode, I'm really excited to bring to you a very special guest, a marketer who has literally done everything in her career that you could possibly do. She has started her own successful marketing agency. She has excelled both as a fractional CMO and in-house CMO. She teaches marketing as an adjunct professor in a prestigious university, and on her spare time, she also contributes to Forbes. She has truly left no stone unturned in her career. And we dive into it. Dr. Amy Osmond-Cook and I, we talk about her career, how it is nothing, nothing close to a straight line, more dynamic and squiggly and messy, how she's had to navigate her own personal ambition and desire and love for what she does with her personal life and her family and being a woman in the field. Like, it's a really beautiful conversation to show that not one path leads to success. And if you are a marketer who feels very much in the messy middle of your career, you're really going to enjoy this conversation with Amy. So get ready for a super enlightening conversation that covers all of this and so much more. Let's make it rain on today's episode. Amy, welcome to the Rainmaker Podcast.

Well, thank you so much, Veronica. It is so great to reconnect and I super appreciate you having me.

Yeah, I'm actually really excited to talk to you because your career is a lot like my career. I would describe it more squiggly than like—

it is, it's a long and winding road.

Yes. And I think a lot of marketers are experiencing the same idea. Like, if you, if you thought that your career was going to be this corporate ladder ascension of perfection, it is not. It is very much this twisty-turny kind of squiggly career path of sorts, and yours is very similar. And so I, with your permission, I wanted to kind of go into it to understand, you know, what did you learn about yourself in the process? When did you know it was time to leave or stay? Like, that's a lot of these, you know, analysis paralysis moments between the shifts, between the twists and the turns, and I just wanted to Dive right in. Are you cool with that?

I love it. Yes, absolutely.

Okay, cool. So let's take it back to the baby, baby marketer Amy back in the day. Why did you even choose this career path? Let's just start with that. Like, what was it about marketing that— the calling of the wild— that this was the profession for you?

This was the place for me. I actually completely fell into it backwards. So I have a PhD in organizational rhetoric, which is how organizations persuade. So you can see naturally that is a very good fit for marketing. But I didn't anticipate it. I got my PhD when I got divorced and I had two little kids and I thought, well, what can I do? I feel like a professor job would be really flexible. And so that was my motivation for that. Then I got remarried and we had two more kids. And then my husband lost his job in the— he got a job with Lehman Brothers, lost it one month later because everything fell out of the bottom in the financial crash of 2008. 8, 9. And so all of a sudden we had these, all these little kids, and it was go time. And so I started just trying to do whatever I could. I was a good writer and I was scrappy, and so I found that marketing content was being very well received, and I was able to do it remotely. I was able to still stay home with some, with my kiddos because they were so little. And then it, one thing turned into another. So they, um people would say, okay, well, you, you can write, but can you design? You can write and design, can you build a website? And so I couldn't. I needed help and I needed people to help me out. And so I formed a company, a small agency that has grown over time over the past 15 years, and I've just had the best time doing it. Meanwhile, one of my clients, Ryan Westwood from Simplus, asked me to come in-house and be his a full-time head of marketing, which it took me about 0.1 seconds to say, yes, absolutely, of course. So I left the agency just kind of running itself and went in-house because there was so much for me to learn. So, um, I did that for 6 years. It was 3 years until the acquisition and then 3 years at Infosys, which I also loved. And then as of April, I am now back at Stage Marketing and with a lot more understanding about how the world works. And how business works and how marketing works.

Yeah, it's interesting because like, yes, I technically have a degree in marketing, and yes, you know, you can go the formal education institution route to say that you're a marketer. But the beauty of, I think, the art and science of marketing, it is very intuitive because it's all based off like consumer behavior. So like, what would appeal to you, or what messages and hooks and things like that. So like, as long as you have that creativity, or as long as you have kind of that empathy, or that you can read people well, like, these are some inherent, you know, skills that you that you don't have to learn at a university to be a really effective and efficient marketer, in my personal opinion.

100%. Yeah, I want to like touch on that too, because at our agency we have about 50 people employed, and I would say about half of them have a degree in marketing, and the rest either have a degree in something else or they don't have a degree, and they're just really, really good at their jobs. I really value people who have a strong work ethic, who are great at what they do, and have a mindset of learning, but it doesn't have to be formal learning.

So yeah, actually I'm really glad that you brought that up because we see the same thing. So I have like a— I curate a whole bunch of Rainmakers. That's what I call us marketing leaders. We make it rain. And so I curate these Rainmakers, I mentor these Rainmakers, and I show them how to be the best leader they can be. But you're right, if I looked at the background of all of the Rainmakers in our program, they're not all these like 15-year marketing pedigrees. In fact, some of our best Rainmakers are like former school teachers or executive assistants or tech VAs. But their emotional intelligence is through the roof.

Mm-hmm.

They're empathetic. They have an affinity for the craft. They have an affinity for people management. So they do really, really well, even if they don't have the degrees to say that they're this like elite marketer. Um, so it's really interesting that you notice that in staffing your agency, a marketing services agency, that you're seeing that with your own staff as well.

It's interesting too, because the other thing about it is that we lean in very heavily to customer service. Because one thing that I've found over the years is that everyone has great ideas. Your finance guy can, can have the most brilliant marketing campaign and just not the ability to bring it to fulfillment. So if we hire people at the agency who prioritize customer service, customer success, communication, um, and some of those values that you were talking about just now, we can help pull out the greatness of marketing with it. Everybody's got these great ideas. So, you know, our job becomes not just to create ideas but also to collect ideas and to amplify vision.

So would you say that great marketers aren't necessarily idea makers but they're idea harvesters in a way?

I would say so. I think that there are some who are amazing idea makers that come up with brilliant campaigns, and I think that some marketers are really, really good at harvesting those ideas. One of the things when I do CMO work for companies, um, my goal as the CMO is to amplify the vision of the CEO. The CEO, generally speaking, knows exactly where the business is supposed to go, has amazing marketing ideas, and is really kind of the chief marketer, right? But especially in startups where they've converted the business, but they don't always have the ability or the time or the interest to execute and to amplify, like, to, to get their voice out there. So my job is really to amplify.

Yeah, no, I appreciate that. I definitely see that with startups as opposed to funded organizations or traditional business models. Yeah, like when, when I'm working with a CEO who has had to eat what they hunt, they're pretty crafty marketers themselves.

That's right, they understand their audience really well.

Yeah, in order to make it, for sure, to validate that product in the early stages. Okay, so your career, even if I pulled up your LinkedIn There's, look, I mean, look at this thing. It's, there's some healthcare, there's some, there's some healthcare, there's some Salesforce going on. There's, I mean, there's VP, there's chief, there's director, there's global. There's lots of titles, lots of different business verticals. And now I know what you're doing. You're back in the agency life and being that fractional CMO, but can we go back to the days between all of these different, I mean, gosh, like what was it like? What's the difference between working for a healthcare organization versus a startup? Like from a marketing standpoint, what do you think?

It's so different.

Is it? Okay, tell me.

It is unbelievable. So I went from a, it was a small, medium-sized business. I was the head of marketing at a company called North American Healthcare. Super grateful for that opportunity. I learned a ton. I worked with skilled nursing facilities. So I would tell, then I went into the startup world in a Salesforce consultancy. And when people were like, well, what did you do at your previous job? And I said, I made nursing homes look sexy. Like that is, that was my job. Okay. To help, help, you know, accurately promote what the goodness that was going on there and the excellent patient care and all of that. But, you know, it was definitely a challenge sometimes to navigate all of the laws. It's the second most regulated industry out there. And so it is, you know, being able to show patients was a no-go. Stock photos didn't look good. There's some really interesting challenges in that aspect. Business tends to go a little bit more slowly than a startup, but it's also very, very regulated and very, very focused on that, that kind of, you know, dot your i's and cross your t's, as opposed to a startup where it was like, hey, let's see what we can get away with.

Let's see if the lawyers can catch up.

That's funny.

Um, well, it's interesting because that's— I, so I have a lot of my background now is in the digital marketing space, and it's, I mean, lightning fast, so fast. There's never enough time. Time— I often hear marketers describe their relationship with time as like a really crappy boyfriend. Like, it's just, he's abusive. It's— there's never— it's never good enough. Like, time is always like this villain for the marketer that has limited everything to do the impossible. But then you're describing work being a marketer for a healthcare industry, an industry that is actually known for going slow. So like, how did you— how did that not deflate you? Because I'd like to think that marketers, there's an— I mean, we are, we like the pace, we like the, the producer in the box, like camera sticks, like there's a part of us that likes the, the energy of the arena, so to speak. So how did you handle it?

Definitely. Well, I really enjoyed both aspects of it. I really enjoy being able to take, you know, there is some more, a little more education involved in the healthcare company when you come from tech. And that's one of the things I've made some mistakes trying to pull things I've learned in tech that are very, you know, very well received and trying to put them into healthcare. Sometimes they work and sometimes they don't. Sure. And so I actually made some mistakes doing that, but it's very fun for me to be able to lean into that education piece. And to watch people get excited about what, what is possible on the web, you know, what can you do to get the word out. And so that's been, that's been really exciting on that end.

Well, and teaching's in your blood because part of what you do, I mean, you've been on different university faculties or boards or things like that. So talk to me about being an adjunct professor and being— I mean, like, talk to me about the, the marketer teacher inside of you.

Of course. So the, it's so much, so much fun to talk about marketing. I could talk about it all day long. I actually went to coffee with the CMO of Xactly on Monday and we sat there for an hour and just talked about marketing attribution. It was so much fun. And sometimes like Veronica, right? Don't you kind of feel as a marketer that like when you can find somebody who can like, oh yeah, talk shop. Yes. And almost like a therapy session. Like we came out of that and we were like, I just feel great, you know. And he was wonderful, and, and I learned a lot from him. So, you know, I think that marketing is a million little things. It's always educating yourself, it's always making things better and tweaking and growing and testing. And that's really the heart of academics as well. And so there's a really a big crossover.

Well, and completely. And I— what I have found, they're very generous spaces and generous rooms, but there's generous professionals. I find marketers to be very generous. Um, I think because we understand that by the time marketing is printed in a book, that it's already like antiquated and outdated. And so there is this need in all of us to like pay it forward or to pass knowledge from one to the other to help each other. I, I find that a lot, whether you're working for opposing companies or not. There's this like kinship amongst marketers to help each other out because everything is so fast-moving and you always feel like you're behind. I mean, in some ways because of the way that technology is rapidly changing.

No, I totally agree. And the fact that CMO's tenure is only around 18 months is really tricky too. I, I feel like I, I admire marketers probably more than any other profession because you have to be so smart, you have to be technologically savvy, you have to have art inside of you. You have to understand the science. There are a million little things that could go wrong, and you have to pay attention to all of it. You have to do it extremely fast-paced. And with everybody saying, why do we need marketing again? It's such a thankless job. So we have to stick together, and it is wonderful when we create something that's really—

I, um, I was doing some research recently, so I'm gonna, I'm gonna validate everything that you just said. So I saw some pretty, pretty crazy statistics. So I have 3 of them. 83% of marketing leaders report experiencing burnout. The average tenure of a CMO is at an all-time low in the past decade. And the CMO's tenure of 18 to 2 years, like you were saying, is the average, or it's the shortest tenure of the entire C-suite. Mm-hmm. So of the entire C-suite, CFO and all the other ones, we're the ones that come in and come out the fastest.

Mm-hmm. Yes, I know. It is definitely, it is definitely not an easy job. Job, but it's also so fun too. I mean, we get to create stuff and we get to launch campaigns and host fun parties, and all of those things are just so much fun, right?

Well, I want to— I, I want you to speak to that because I, I haven't quit, right? So I know that a lot of marketers, when they don't take care of themselves or they're not being properly mentored or they're not being surrounded by other gracious and generous, you know, mentors and marketers, like, we burn out, we churn out, we turn out. Like, that's That's unfortunately one of the side effects of this industry, which is relentless. But I've made it. I've been here for 15+ years. You've obviously made it. We're in the long game now at this point in our careers. How does one stay? How have you been able to stay? And like, be radically honest. Sometimes does it take— where you've stepped back from it, where you've come back to it? Like, I'm curious how you are still in the game this many years later.

Thank you for saying that. I think that it— I again admire everyone who makes a career out of this, and it— I think that intrinsically it's so much fun. Like, I really, really enjoy the campaigns. I enjoy the work. I enjoy creating. Um, so for me, like, I— it's a very good fit for me to do that. I also try to stay in the project, um, a little bit more than high level, looking at numbers. Stresses me out. I like to get in there and get my hands dirty. I also think that who you work with makes all the difference in the world. We have— our team is just absolutely phenomenal. We really prize 4 values when we hire people: kindness, quality, flexibility, and grit. And when we hire someone with all 4 of those qualities, it's, it's kind of magical, and it is something that, you know, being able to produce those kinds of, you know, quality campaigns and being able to get to know people and, you know, actually, you know, make good friends in the process has been super helpful for me as well. Also, I think, you know, just being radically honest, it's tough. And I actually have gotten myself a therapist on occasion. I have gone on long walks. I have tried to, you know, I've worked long hours. You know, my meetings typically start at 6 AM and oftentimes I'm working at night. So if you don't really love it, it's tricky. But I try to take breaks in the day. So even though those are really long hours, it, you know, kind of breaks it up for me. So that's really helpful too. I don't know, what do you do to kind of help you?

Yeah, I was just thinking about what you just said. I mean, I think like you said, being with people that you can vent to that like just get it. I'm no stranger to working with internists. So whether it's a therapist or a coach or an integration expert or things like that nature, I worked a lot as a female to regulate my cortisol levels, my hormone levels, because I also am a mom of littles. And so I think being a female leader has a layer that our male counterparts do not have to necessarily deal with as much as we do when it comes to the physicality of our bodies. Also paired with the season in which I am advancing in my career, because I started— I mean, I graduated at 20 years old, and like in your 20s, you're, you know, you're getting married, you're having babies and all the things, you know, obviously if that's what you want to do. But that was my story. And so that's happening in my 20s, between 25 to 30, and now 30 to 35. Now my kids are, you know, they're in and I have school schedules. So, like, if I track my career advancement also with the ages of my children and that and the physicality of what's happened to me and my body at the same time, it's a lot in a very little period of— I mean, it's a lot.

Mm-hmm. It is.

Because I have way more responsibilities at work. There's more pressure. There's more spotlight. There's more all the things. And I wanted it. I'm highly ambitious. I still am.

Yeah.

But I also have extreme family values that I don't want to jeopardize or compromise. And so like that actually has been some of the hardest tension is to hold space for both of those realities without suffering.

You know what? It's so true. I came to a point in my career about 10 years ago where I kind of had a conversation with myself and I said, self, if you do this, you can't have any friends. Your friends are going to be work friends and you are going to be able to be kind of on the fringes, but you're not going to be able to put put the time in that you have once done and you probably want and probably need. But for me, that was the choice that I made to prioritize my work and my family. And, and so unfortunately, like, some of those other relationships had to take a back seat. But what was so amazing about it is I found just as great of friends who are in the same situation as me. So I felt like I didn't really have to, you know, like Like sometimes it would be hard to watch people going to play tennis and I'm sitting here on a call and whatever. You have to give stuff up. But from my perspective, I'm really happy with the choices that I made.

Well, I just love your radical candor. Like the fact that you were mindful enough or aware enough to be like, okay, self, let's have a conversation about what this really requires. And I think that happens a lot in retrospect or hindsight, but like, if you can be present in the moment in your career to be like, okay, this is a particular season, let's just call it. And what is it going to take? Am I wanting to do this? Is the sacrifice worth it? Right?

I think you have to, I think you really have to decide that. You have to say, you know, when I retire one day, I have, I have a whole library of books that I want to read. I have all kinds of things that I want to do. And so, you know, there are lots of things that I have given up in order to to, you know, progress my career. And a lot of people would say, you know, you don't have to— you don't have to give things up, you can do it all. And I don't think that's true. I think that you make your choices.

Yeah, I agree.

You own your choices, and you say, okay, this is what I'm willing to give up in order to make this happen.

Yeah, life is not a life of just simply yeses. It's a life of yes and no. And, and your discernment to when to say yes and when to say no is really how you kind of like get through it. And being surrounded by people and peers can also help you in those discerning moments because it's really hard. And if you're all up in the weeds of it and you're emotionally spun out, it's hard to stay objective. So I completely agree. Hey, Rainmakers, true or false? Becoming a top marketing leader is all about climbing that corporate ladder. False. Such crap advice for modern marketers. The true key to unlocking your career potential in today's landscape? Learning how to promote yourself versus waiting for someone else's validation. Introducing the new Rainmaker Roadmap, your free comprehensive guide to becoming a marketing powerhouse. Master your role, nurture your team, prioritize your well-being, and evolve into the marketing visionary you were meant to be. Grab your roadmap today by going to rainmakerroadmap.com or grab the link in the show notes. Now back to today's episode. I'm curious because like you've worked for a number of different personalities, you are also an employer who who employs a whole bunch of personalities. I find employing marketers is a different breed than working with customer service reps or operations or financial, you know, finance professionals. I guess like qualify or give me the qualities of some of the best employers that you as a marketer felt like you blossomed under. And then what are you trying to pay it forward to the people that you employ too?

That's a wonderful question. So I feel like with all of the people that I've reported to in the past, and I'll just kind of stick with the one, the CEOs that I've worked with. I've learned something really wonderful from each one of them. And I, what I try to do is, again, you know, get, put it in my basket and learn from it. But one of the things that I'm not very good at is confrontation. I typically don't like to address things, and that's just who I am, and it's a terrible leadership quality. So, so I really worked hard to become more straightforward. But at the same time, you want to still be kind and you want to put things in their proper context, right? So one thing that, that I have tried to do, and you can ask my team how well I'm doing it, is try to really contextualize when there's something that needs to be addressed. I want them to know they are wonderful people. I love working with them. There's a particular issue that needs to be addressed quickly. And then we can move on with our lives. And so I really try hard to put that in the proper context, and that helps me be more direct as a leader and say, hey, let's just fix this and move on. Right. Keeping the emotion out of it. So important.

Yeah.

Right. Also, one of the best things I learned as a leader is how to say, how to say you're sorry. You know, there are people, people will take things very differently if the CEO is saying it rather than if your colleague is saying it. So that is one other thing that I learned the hard way was, you know, I can't really speak— if I am the CEO of a company and I say something, I can't say it in the same way that I would tell my brother, right? Or that I would say to my mom or whatever. And so you have to be really careful about, about the meaning behind the actual words, because depending on your position, depending on the context, those same exact words can be infused with a lot of different meaning.

Yeah.

So that's another thing that I've learned. I've also learned how to just pivot quickly. I think I've learned how to address things and move on while they're still, while they're still small. And that's the other reason that I really worked on becoming more direct, because when you are direct and you catch something when it's small, it's just a very small thing and then you move on. If you're reticent to address things and it grows and grows and grows, then you've got a big issue to deal with later on.

Canker.

By the time—

yeah, it's too late, it's cankered.

Yes, well said.

What I guess— I know, and I know our time is winding down, it's— I just really love talking to you.

It's me too.

I, I want you to kind of end on a high, like what's the one thing in your career to this point? Because you've done some really cool stuff, you've worked with some cool people, you're obviously still now providing services for others, you, you employ people. I mean, like there's a lot lot that's on your shoulders. And so I just kind of want to ask you, like, what's the one thing that you're going to give yourself credit for? Like, what are you proud of yourself for in your career?

Huh, no one has ever asked me that before. Thank you, that's very nice of you to say that. I think, I think that I am most proud when I see one of my employees growing and advancing And, you know, I have so many employees who have doubled their salaries while working with me, and it makes me so proud to see them growing in those capacities and taking on more responsibility and being able to have great careers. I think that's what I'm the most proud of.

I love that. I think, I think the truest, most beautiful definition of great leadership is when you make other leaders.

Could not agree more. So, so agree. I think that that's when you know that you've actually given something.

Well, I'm gonna drop all of your links in the show notes so everybody can connect with you on LinkedIn, everybody can get a taste of your brilliance like I have been today. Um, but I just want to thank you so much, Amy, for joining us on today's Rainmaker Podcast.

Thank you so much, Veronica. What a pleasure. Thank you.

Thank you for joining us on today's Rainmaker Podcast. Marketers help other marketers. So if there's a marketer in your life who could really use a new perspective in a way that helps them advance their career, please pass this episode forward, share, like, leave us a review. Everything helps as we embark on helping as many marketers elevate themselves inside and out. You can always visit veronicaromy.com. For today's show notes, additional links to some free resources and tools for you to help you advance your career. You can always connect with us on social media @vieronme if you want more behind the scenes or a way for us to connect personally. Until next time, my friends, make it rain.