Hands-on Leadership: Stay a ‘Player-Coach’ as long as you can (podcast episode #124)

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In marketing, it’s easy to become a manager and lose touch with the craft. Val Riley, VP of Marketing & Strategy at Unbounce, has embraced the ‘Player-Coach’ mindset, blending leadership with hands-on execution to stay relevant and drive results.

I sat down with her to discuss how she learned that lesson, along with many more lesson-filled stories from her career. Hear the full episode using this embedded player or by clicking through to your preferred audio streaming service using the links below it.

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Stories (with lessons) about what she made in marketing

Take risks to propel your career

Riley left a very cushy, safe job in a stable company to go work for a start-up that had just reached product-market fit. Her coworkers, her friends and even her husband all said she was nuts. Riley knew it was the right decision, though. She was at a slow-moving, slow-growth company and she felt like the marketing profession was passing her by.

The role at the startup led to her first head of marketing role at another startup. Without those experiences, she would never have been ready to lead the marketing team at Unbounce.

Stay a ‘Player-Coach’ as long as you can

Even today in the leadership role that Riley is in, she wants to touch real work. At times, this means she is working late or on weekends but so be it. Staying close to work keeps your skills fresh and retains your value in the market.

M & A = Opportunity

Yes, hearing rumors of M&A activity within your company can be scary. It can also be a chance to shine. In every case that Riley has been involved in, she’s been retained and/or promoted (knock on wood!). If you are a star performer with strong inter-departmental ties, your value is high. She’s always strived to be in that spot.

When navigating M&A, ensure your LinkedIn profile is up-to-date and tells a compelling story about your leadership capabilities.

Lessons (with stories) from people she collaborated with

Marketing is like a soccer team

via CMO Andrew Dod

Marketing teams need each other to perform at their best. In sales, you can be a lone wolf and be successful. Not so in marketing. Digital needs creative. Content needs design. Everyone needs marketing ops. The interdependency of marketers is vital to success. This lesson came from her then CMO Andrew Dod. He is now with QmarQ.

Reflect on the day

via COO Barry Pruett

Her COO at ITProTV, Barry Pruett, taught Riley to spend some time at the end of each workday to reflect on her conversations and actions. This is a way to strive to do better every day. You must lean into the moments where you could have done better in order to get better. Today, Pruett is a Business Architect at AWS SaaS Factory.

Why kindness is a competitive advantage in leadership

via CMO Chip House

Her CMO at Insightly, Chip House, was a talented marketer and leader. He was also the nicest person. He was able to deliver feedback in a supportive way that made you think it was your idea. He also ran a lean team which taught Riley to not over hire but rather get the right people in the right seat.

Discussed in this episode

Entertainment Industry Marketing: Never forget the independence of your imagination (podcast episode #121)

Customer Engagement: Marketing case studies from Coors Light, a professional soccer team, and a private jet charter

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Transcript

Not ready for a listen yet? Interested in searching the conversation? No problem. Below is a rough transcript of our discussion.

Val Riley: If the game is really good, the fans don't care about you right? And what that means is like, if the game is tight, everybody is really hyper focused on the game. And you could be doing the craziest antics on the sidelines and no one's paying attention. And I think that that's a good lesson for marketing, because sometimes, no matter how good you are, right, it's just you're not you're not going to reach the audience.

So like, you put out a press release and on the same day that something giant happened, like there's a big slack outage. You know, your press release is not going to get picked up. It wasn't anything you did wrong. It's just sometimes the the audience isn't paying attention to you. And so I think that was a good lesson.

Like literally on the field, you know, cut your losses, go in. And then when it's a blowout, boy, everybody wants to see Alberta every day. All the little children that people pass, see their babies and be like, here, hold my baby while I take a picture.

Intro: Welcome to how I made it in marketing. From marketing Sherpa, we scour pitches from hundreds of creative leaders and uncover specific examples, not just trending ideas or buzzword laden schmaltz. Real world examples to help you transform yourself as a marketer. Now here's your host. The senior Director of Content and Marketing at Marketing Sherpa, Daniel Burstein, to tell you about today's guest and.

Daniel Burstein: I remember when I got hired at my first agency job out of college. In the interview process, one of the people interviewing me had recently been promoted to creative director. Now he was interviewing me. Okay, but I saw an opportunity to interview him as well because being a college student at the time, that was my goal, my career to grow, to be a creative director.

So when I asked him what it was like, I'll never forget what he told me. He said, well, I used to get to make things to create, which is what I really love. Now I mostly manage people and processes and that insight always stuck with me. I've always tried to keep my pen on the paper, even when I had to manage a team.

So a lesson I read in a recent podcast Guest application really resonated with me. Stay a player coach as long as you can. Joining me now to share the story behind that lesson, along with many more lesson filled stories, is Val Reilly, VP of Marketing and Strategy at Unbound. Thanks for joining me, Val.

Val Riley: So happy to be here, Danielle. Thank you.

Daniel Burstein: All right. Let's take a quick look at Val's backgrounds and who I'm talking to. She was director of content and product marketing at Sharp Spring, VP of content and category marketing at Ipro TV. And for the past three years she's been at Insightly, which was recently acquired by unbound, where she is a vice president of marketing and strategy.

As I mentioned, Insightly is owned by unbound and its most recent funding, round, Unbound, raised $38.4 million and has 15,000 customers. Val manages a team of 16 with a budget of $4.5 million. The Val give us a sense. What is your day like as VP of Marketing and Strategy?

Val Riley: Yeah, well, I'll I'll zoom out and say like what a typical week looks like. I like to front load my week with, meetings that are my team meetings, one on ones and being part of the leadership team. That's a that's a long, a big part of my job. And it's a big part of the, of the meeting landscape.

So Monday, Tuesday and Wednesday, I'm really in a lot of meetings touching base with folks, moving projects along and keeping abreast of situations. And then as the week progresses, I get to be a little bit more creative, a little bit more hands on. We'll have project discussions, brainstorming sessions. We'll have, I'll actually roll up my sleeves and do some work on.

I love to have my hand in writing. I love to have my hand in, and design concepts, etc.. So towards the end of the week, I'm definitely flexing more of that creative muscle.

Daniel Burstein: You know, I've asked a question to a lot of people and a lot of people talk in de parts like, okay, in the morning I got my in the afternoon this I like you're thinking of the big picture, right. Let me get this stuff done in the beginning of the week so I can get that creative stuff going in the end of the week.

I like that.

Val Riley: I also have the, benefit, I think. I think it's a benefit of being across, three time zones. So we have folks on the east coast of the US and the west coast of the US. So you can usually find some time if you're an east coast, to find a little time in the morning when it's quiet and if you're a West Coaster at that time in the afternoon.

So I like to think we chase the sun a little bit and kind of keep those, those quiet times precious. But then the time in the middle of the day, we're just all available to each other and really making the most of those hours.

Daniel Burstein: Yeah, I like that as well. Working with people on the West Coast, I find my mornings I can be a little, a little more undisturbed and kind of get going in the morning and really focus on some things before the meetings hit. The meetings that. Okay. Let's take a look at some of the lessons that Val has learned from her career.

I always like to say that's a really cool thing we get to do as marketers. I've never done anything else. I've never been an actuary or a podiatrist. But, like, I don't know that they make things. We make things. So, the first lesson she learned from the career she has made is take a chance. So how did you take a chance?

Val Riley: Yeah. So I was lucky enough to start with a technology company pretty early in my career, and it wasn't my intention, but I ended up staying there for 16 years. And it's just like every time I was, I was thinking about leaving. Something would happen. For instance, you know, there was the financial crisis that happened, and all of a sudden, like, no one was looking for a job and no one was hiring or, or I would think about taking a new position and then something interesting would happen at the company where I would be like, oh, maybe I should stay a little bit longer.

But, you know, 16 years is a is a real long time. While I was there was a software company. We started when I started, we had mainframe and client server applications and really SAS was born during those years. And so I got to launch the first SAS application that that company had. So it was 16 years.

It was a long time. There was a lot of change. But I do look back at that time and wonder, maybe it was I stayed a little bit too long, because there does there you hit a ceiling with your growth sometimes or and you're I remember I went to a conference and I had been at that point, it had been 15 years.

I went to a conference, and I was just sitting there and hearing terminology and acronyms and seeing tech that I was not familiar with. And I sort of started feeling like the the industry, the career was passing me by. And so I got a little worried, thought, okay, well, maybe I'm not doing myself a service with this long tenure at this company.

And so I was reached out to by a recruiter to go work on a startup and it was a startup that had product market fit. So it wasn't brand new. Crazy craziness, but it was really early stage. And I looked at myself and I thought, this is the opportunity that's knocking, and if I don't take it, I'm going to stay at this company and I will probably retire here.

But I could take this chance and go work for this startup and see if I have what it takes. And it was really crazy. My friends told me not to take the job. My husband told me not to take the job. My colleagues said I was nuts. I had this really cushy job. I was coming and going as I please.

I had a private office, like everything was great and I just knew in my heart that this, this was it. This was my chance to see if I could really do it. And so I left that cushy job and went to a startup, and it just kind of skyrocketed my career. So I'm glad I did it.

Daniel Burstein: Okay. Something I always like to do with our guests on how I made it in marketing. Like, it's not like, you know, with like, oh, we all agree on everything and let's move on to that thing or this thing I always like. Let's look at the opposite of that. Okay. Let's look at the opposite. What you're doing. I agree with what you're saying.

We should take a chance and make sense 16 years to go to a new firm. But in those 16 years at that company, did you ever take a chance and take on something new and still be able to grow internally at the company? And I ask you this because, well, two reasons. One, I've been here 16 years. It's funny, this is my 16th year in partnership with Mac Labs.

I but the other reason is I kind of hear this thing always, especially in our industry and a lot of industry, especially in our industry, where it's like every 18 months, you gotta be moving. If you're not moving, you know, you're not moving up, then you're moving down, you know, and it seems like, when I look at, you know, some LinkedIn's or, you know, or just hear about some people's careers, it's just this constant churn in these different companies.

And I can see a benefit in that. But one thing I will say and have been in, having been here 16 years is, it's like that famous quote, like, you can't step in the same river twice. It's not like it's been the same company for 16 years. We're in a fast moving industry, like what I was doing in 2009, where it's like a blog was a key point of what we were doing in like a webinar and stuff.

And now, you know, AI and all these different things we've done. And so what I've always tried to do is even reinvent my career with the opportunity within here, because the longer you're at a place more influence you have, the more ability you have to shape the company and not just your career to shape the strategic direction and to launch new initiatives that you want to do without necessarily having to externally.

Now saying that, of course, what you did was right. A lot of people should go to different jobs. I just wonder if you have any thoughts or examples of in that 16 years at the company wasn't necessarily just I'm sure you weren't sitting on your hands. You seem like a very, you know, outgoing and, adventurous person, like were there examples of you're like, okay, let me either take my personal career or department or company in a new direction without having to leave yet.

Val Riley: There were some spots in there where I do feel like I had growth. I mean, I was promoted multiple times. I think my skills and talents were definitely recognized. I also feel like no one will ever look at my resume and say, well, this, this is a person who isn't loyal, right? Because I definitely have proven that given the right circumstances, I'm not a job hopper.

I will definitely stay long term and and write out good times and bad times with the company. So I think those were both positives. Also, you know, again, during that time software made great changes that where we had basically launched software as a service. Right up until then everything was client server. And so I got to be on the team that launched the very first web app and that company.

And so to be there for the birth of sass, really to experience that, but in an environment that was very safe and stable was really a blessing because I got to really understand what it took to put put sass together and get it out the door. But I wasn't in an unstable environment or an environment where funding was running out.

It was a very stable, slow growth company, and so there were those benefits as well, of being able to learn and not being under the gun for results, because the it was a privately held company that had very, realistic growth expectations.

Daniel Burstein: Well, when you talk about growing in your career, I really love this next lesson. Stay a player coach as long as you can. I feel that I felt that my career, like I said in the beginning, tell me the story. How did you learn this lesson? How do you live it now?

Val Riley: Yeah, it's super important to me, for a lot of reasons, but mostly because I feel like marketing changes so fast. I used to joke with my old CFO, who was great. I mean, we had a great relationship. I was the head of marketing. And she, I always came within 5% of budget every month. So I think that's why she liked me.

But I think she really, genuinely liked me. And, And I would joke with her about, like, sometimes your job looks really great to me because when I look at, I can't imagine there are a lot of different ways to read a balance sheet. I can't imagine that technology in finance is that is that disruptive? Right? Like essentially at the end of the day, we're making budgets, we're doing producing statements.

We're closing out the month. I really feel like in marketing, if you don't keep your finger on the pulse, you will be so lost so quickly. Like every week, every maybe even every day. There's new terminology, there's new acronyms, there's new tech. There's always something new happening in our field. And so it can feel, if you don't keep hands on, if you end up becoming like, oh, well, I'm just somebody who manages people who do the work, and you remove yourself one step from the actual hands on work.

I feel like in marketing that is like signing the death warrant of your career. I can't imagine that's the same in finance. I really do feel like you could be a little bit less hands on, for example. But with the the way martech moves, with the way, just different, technology, different methods. You know, we had our funnel, then we flipped our funnel.

It was all ABM. And then it was all, you know, like waterfall, like it's there's always something new in marketing and if you are just managing people, in my opinion, you're you're doing yourself a disservice. I was I, I feel comfortable personally and with maybe for direct reports. I feel like that's the right number for me. I was recently challenged by my CEO.

He's like, you know, you should really have more like 6 or 7 direct reports and I have done that. I have added more direct reports because that's the the company that I'm in right now. But I will tell you, I'm just working extra to still keep hands on because my fear was adding two more direct reports, two more one on ones every week.

I feel like that's taking me away from the real work of marketing. And it's a fear of mine because I. I don't want to lose touch with the day to day, hands on work that marketers do. It's also the most fulfilling thing that we do. So you really don't want to lose that if you're just end up managing people?

I feel like it just takes the spark out of what is an amazing career.

Daniel Burstein: Well, I'm glad you mentioned that fulfillment. That's what I was to say. I remember I was an advertising major at UF. There's something we have in common and I don't know why you chose it, but I remember I think, I think it was we'll haul whatever it was. When you first meet your admin, you sit down before your freshman and they're like, watch what major do you want?

And so University of Florida is a big school and there's a lot of majors. And I remember looking like I really want to be a film major. Like that's what I want to do. But I'm like, I am not going to get a job as a film major. Like, I should probably be a business major, but that sounds boring.

And then I saw that major advertising and I'm like, well, this scene's kind of half and half, right? You got the business piece and I was a business minor, but you get to have the creativity of it. So it's like that fulfillment piece. I love that of like, okay, this is business administration. I don't know, I'm sure there's some people who are operational folks and that's great for them.

That's not why I got into this, you know. But the piece I really want to ask you about, because I'm glad you mentioned your direct reports, is, does staying a player coach help you make sure your team executes better? Like, do you have an example or a story of that? And having that hands on acumen helped you execute better because, for example, I interviewed, on how I made a marketing.

Jeffrey Kyle holds the SVP of Marketing and Broadway Licensing Global, and one of his key lessons was execution sets people apart, right? And that's so true in marketing. Yes, we're an ideas industry, but I know a lot of people who can come up with a lot of ideas and they're not leaving marketing departments because they can't get it done.

And so what I've seen, like when I've managed teams, is when you have that hands on experience, you know how to overcome the bottlenecks, right? You know, when the budget is off, you know, when the, you know, timelines are off, projects are off. So even though it's like, you know, any good business manager operational person can manage some of those things to some extent.

They don't understand what that creation process, budget all all that all those elements are like. And that's where it really makes a difference. Still having your hands and things. So I wonder for you if you had any example or story you can think of, of like, oh, being that kind of player coach person, it's not just okay that my personal fulfillment or staying up to date on things, it's I can make sure our team executes because I know, like, I know what I'm told, the right thing or the wrong thing, or I can help my team just overcome the bottlenecks that they're facing.

Val Riley: Yeah, I feel like one example, like a picture is worth a thousand words, right? Like I can sit here and describe what I want the landing page to look like. And I can say, well, take this from here, take that from there, etc. but I also can hands on enough. I can go into Adobe XD I can open up, open it up, I can paste in different parts of different landing pages, type in the words that I want, and kind of make a very rough, rudimentary mockup and give it to the designers and say, this is what I'm thinking, and then they can take that.

That's their iteration one, and they iterate. And then from there, I'm getting exactly what my vision is versus me having to, like, not have the ability to use XD I mean, I just can't imagine being a marketing leader and not having access to the Adobe Creative Suite. Like I just have to be able to communicate in the language that my team uses.

So, you know, just again, just doing a quick mockup, just or even for an ad or we can here's what I'm thinking. And so they know what my vision is. And I'll tell you 90% of the time they take it and they make it so much more amazing than I ever envisioned it could be, which is great, but I just feel like because I'm hands on, because I have those tools, I get us to first base a lot faster, and then they take it and they hit the home run.

So just one example, but I feel like there are a million now.

Daniel Burstein: That's great. Clarity of direction. The worst thing to do for your team is not a good clear direction. I remember working on a tagline once at an agency, and I wasn't hitting it, and I didn't know what I was missing in my boss was it had a big, thick dictionary on his desk and just puts his hand on the dictionary.

It's like it's in there somewhere. Like, I mean, I need a little better feedback than that, but all right, let's talk about kind of some more of that kind of business element in the growth of your career. You said M&A equals opportunity. So kind of take us through the story. How did that how did this happen?

Val Riley: Yeah. So I mean, if you're in SAS right now, you have either been purchased are about to be purchased, about to be merged like it's just all over. It's prolific. I really do feel like 2025 is going to be huge for that to like. I think you have all these PE firms sitting on money and and it's their job to deploy capital and like listen, they've got to start deploying capital.

So if you haven't been a been a part of M&A activity I'm telling you it's coming. And so this is my third time being involved in M&A activity. And I had always had this fear of oh well, like if that happens you know people lose their jobs. And and it's true sometimes in mergers and acquisitions there are, you know, redundancies in my experience though, and I think it goes back to being a player coach.

In my experience, I have always come out on top of M&A activity. I have always advanced, gotten a new title, additional responsibility. I was always retained and again, because I'm hands on and I manage because I think I'm a hard worker. I think I'm someone who produces, I it has always worked out well for me. So I say to people don't necessarily see a merger or acquisition coming down the road and think, oh, panic time, let me get my LinkedIn ready.

Let me start applying for jobs like crazy, because it could end up, if it has for me two times, knock on wood, that it has. I have ended up in a in a higher position with additional responsibilities and sometimes even additional pay, just because I brought to the table like a quality skill set of player coach that, was deemed valuable by the acquirer.

Daniel Burstein: Okay, so give us a playbook if you will. Right. So let's say someone listening right now, right before they tune in. They're they're driving home right before they drove home. They got the email were getting acquired, were merging with whatever. They're going to go into work tomorrow morning, the next week, the next month. Like what are the three things they should do?

Because what you mentioned about player coach, I think that's so important. There are some of these things obviously we should do way before a merger acquisition happens, just in general to position ourselves in our career, do the right things for our company, do the right things for our career. But let's say it just happened. Now, what if you said that if you sat down with them, you know you've gone through this three times yourself, what are a few things they should do tomorrow morning, next week, next month as this kind of M&A rolls out because this tends to be like an instant hit, a shock to the system.

And then this kind of I don't know, would you call it messy marriage over several months? Partly depends also if the companies are public or not. And then there's a lot of stuff going on in the news too. But but what advice would you give?

Val Riley: Okay, I love the term messy marriage. I'm definitely stealing that. So here's something I this is a real tip that I learned and I did not know before. Just before our merger, our CEO was able to go into a stealth mode and view the LinkedIn profiles of all of the team members of the marketing team that was being acquired.

So and in this case, there was, there was a, an opportunity for marketing leadership, right? That the CEO saw. And he said, well, we're about to buy this company. Let's see who's in, who's in this company to see if maybe somebody here could end up leading the team. That was me. But the lesson is my LinkedIn was perfectly up to date.

I told a good narrative, a good story about what I do, what I bring to the table and what my skill set was, even though in my current role. But just before the, merger, I was not leading a team. I had previously led a team before, and so my narrative and LinkedIn talked about that experience. And so that's why I was tapped to lead the joint and bounce insight team after the acquisition.

So people can look at your LinkedIn and stealth mode. They have the skills. I had no idea it was happening, but luckily my LinkedIn profile was up to date and it was a good representation of my skills and what I bring to the table. So I would say everybody who can hear my voice, just make sure you've got a really good story there and you're accurately representing your skills because you don't know who is looking and you think you know who is looking because LinkedIn says so.

And so I looked at your profile. There is a stealth mode. They can see without you seeing. So big takeaway.

Daniel Burstein: That's interesting. I never knew that. I never knew about it.

Val Riley: I did not either.

Daniel Burstein: So well, maybe when you go to your LinkedIn to get a few referrals from former colleagues, and then we're going to talk about Nexus. We just talked about some of the things about how valve built her career. But in just a moment, we're going to talk about some of the people she built them with, because that's what we get to do as marketers.

We build things, we build a career. We will build them with people. But before we get there, I should mention that the how I Made It a marketing podcast is underwritten by McLeod's. I, the parent company of marketing Sherpa. You can get conversion focused training from the lab that helped pioneer the conversion industry in our AI guild.

Grab your free three month scholarship to the AI Guild at Joint Mech Labs ai.com that's joining NEC labs B.Com and learn how to use artificial intelligence and conversion optimization to improve your results and your career. All right. Let's talk about some of the people, from your career that really had an impact on you that you learn from.

The first person you mentioned was CMO Andrew Dodd. And from Andrew, you said you learned that marketing is like a soccer team. How did you learn this from Andrew?

Val Riley: I love this analogy and I think it's so true. So basically, if you think about a basketball team, right, the court is fairly small. You've got five players. If you've got Michael Jordan or LeBron James or Steph Curry on your team, you're going to score a lot of points and you're going to be in contention for every game.

Again, the field is the court is fairly small. The number of players there's only five. So really one player can have an impact. But Andrew said that marketing is like a soccer team. The field is huge. There's a ton of players and just one person does not make a difference. And if you really want to take the sports metaphor, you can look at David Beckham when he went and played in the States and how he lost a ton.

Right. And you would think if you have David Beckham on your team, you're going to win. Not necessarily because soccer requires coordination. It requires the pass. So think about marketing, right? Your content writers can have the best copy, and if it gets in an ad and the design is poor, it's not going to convert. Or maybe the content team writes a great copy.

They give it to the design team. The design team kills it. Super great visual and you're paid media person runs that ad in the wrong to the wrong audience. Guess what? It's not converting. You know, or you know, same thing. You can write a great email, but the marketing person sends it to the wrong segment and it fails.

So like we all need each other. There isn't a superstar. Everybody relies on the pass. So we are a soccer team, and you really have to like the players that you're working with. You really have to respect them. You have to trust that when you pass that they're going to do what they need to do and then do the next pass.

That's the only way we score. And so I really felt like that analogy rang true for me. You know, you could be on a team of four, eight, 1030, but you still have those passes and you still need to rely on other people. The only way we're successful is if we all are working towards the same goal and on the same page, so that, you know, it's not a it's not a Michael Jordan, it's it's more of a David Beckham.

And I really feel like that analogy resonates with folks.

Daniel Burstein: I love analogies as marketers. It's like part of the creative. We just we just don't understand the world. So I want to extend this analogy. I'm going to try here. Let's see if this works. Okay. So we got marketing is like a soccer team. Then the customers come like the fan right. Is that does that work. So I want to ask you an example of okay you're together with your team.

Do you have any examples of how you put the customer first as a team? Because I think that's one of the biggest challenges we have is market. So as marketing we've done research. We found customer first marketing so much more effective, which is great. It is difficult to put the customer first. But so one example, to use a literal example of a company, a brand, I wrote a case study with Valencia C.F., the soccer team, and during Covid, right.

They had a significant challenge because they could not during the pandemic. They cannot have people come into their stadium. They literally could not serve their customer. And so what they did is, you know, they went digital. They came up with all these digital interactive formats, quizzes, polls, test games, you know, voting on favorite jerseys, getting prizes. And so the way they did was they put their customer first during all this craziness or like, here's some ways we can interact.

And they also put this other customer that they have first, because they had Ted sponsors who now couldn't get in front of people in the stadium right? So they had kind of some inventory for the sponsors. And so they found even in they were this difficult way. They found a way to like, okay, let's let's raise up the fan or the customer.

So using your knowledge, you may be painfully extending it. Do you have any examples of how your soccer team, you know, puts the customer first? Sometimes that's a trade off. Sometimes, you know, there is something short term we're going to take a hit. But long term it's going to help the customer.

Val Riley: Yeah. Well I think the essence of the soccer team puts the customer first. Right. So again like LeBron James takes the ball and he's going to the basket. No one's stopping him right. It could be good. It could not be good. He could be thinking about the customer. Or he could not be thinking about the customer. But the essence of the past is that, you know, the writer is relying on the designer.

The designer's relying on the on the paid media person, the operations person. But each of those people can have a customer lens. So you get like a check at every point. It's not like you're just saying, oh, one person is going to run with this. You everybody's in it. So everybody has a chance to say, hey, maybe this copy isn't perfect copy team, or maybe this copy isn't working with the visual.

Maybe we should huddle and see if we can make this better, or the paid media person gets it and says, you know, hey, I'm just going to I'm going to push this back a little bit and say, hey, I'm not sure if this I have the right audience for this. What are we trying to achieve? So I think it's just those little checkpoints that are just inherent in the past that put the customer first, because you have so many people bringing their customer lens to everything versus just one person, you know, railroading something down the down the lane.

Daniel Burstein: So, yeah, well, what we're doing now, even in talking about this and something I've heard from a lot of guests, is when we're done recording is you like, wow, you know, I didn't really reflect on my career that much. I kind of just went through and did these things, and I never really took that time to to do that reflection.

I think it's so helpful. So I love one of your lessons. You said literally reflect on the day. This seems like it's something you do every day and you learn this from CFO Barry Pruitt. So how do you learn this from Barry, and how do you use this kind of mindset every day?

Val Riley: Yeah. So, another one to another startup and led the marketing team and was fortunate to work with Barry. And he, had this, this kind of habit that he did at the end of every day where he would, go home and, and before he went to bed, he would just think back to, how did I do today?

How did individual interactions go and where do I think I had my best self, and where do I think maybe I could have expressed myself better or communicated better? And, you know, we all want to think back on the positive stuff that makes us feel good. But thinking back on the negative stuff or things that you feel like maybe didn't go as great is hard.

That's but that's where the growth is. And so what I noticed was, as he was my supervisor a few times, he would just towards the beginning of our relationship, he would come into my office in the morning and say, hey, yesterday when I said this, and he would, you know, backtrack or he would clarify. And I sort of just started noticing this pattern.

And I said to him once, like, I noticed sometimes you you come back in and you tell me something that, you know, we did yesterday that you want to kind of switch up. And he's like, well, here I have this, I have this habit that I do. But every evening I review the day and I was like, wow.

Like that just seemed to me to be such a mature way to approach your professional life. I guess even your personal life, truth be told. Yeah. And so I thought, well, maybe there's a lesson there for me too. And so I started doing it, and I'm going to warn you, it can feel a little uncomfortable because you can think back to stuff and think, oh, like, I really didn't handle that very well.

And so it, it pushes you to become a better professional, a better coworker, a better supervisor to go to your direct report and say, hey, when we had this call yesterday, I wasn't in the best headspace. I think I may have, you know, not come with my full energy. I apologize for that. If you want to reschedule, let's do it.

You know, really coming in and and owning your behavior, is a very mature thing to do. And I think that's a great lesson. And and not the easiest one. But it's definitely one that I've tried to emulate.

Daniel Burstein: Now, I love that. And you said, you know, hey, sometimes we don't want to reflect on the negative. We just reflect on the positive. I mean, for what I've found, really where we are today. And this is kind of where my career has changed since I started imprint. And things have just fast forwarded, you know, with digital. And so it's not even that we're only reflecting on the positive.

We just don't reflect because there's the next deadline and the next results and the next quarter and the next, and we're just on to the next thing and we're on to the next thing. So I love that lesson. But as I mentioned, something we do is reflect on our career. And one thing I've noticed, you know, we often reflect on there's a there's a kind of a timeline in our life that we consider our career.

And when you mentioned LinkedIn, it's funny, it usually starts post college and our first professional job, but sometimes what I've learned is some very early roles we have that seem unrelated to to marketing we can learn a lot from. And an interesting thing about your background is you were Alberta the alligator and I have to ask is there anything you learned from that time being a mascot that you have applied to your career in a specific way?

And for those who don't know, I'll just mention. So again, as I mentioned, you are both alumni of University of Florida. If you haven't heard of it before, I'm sure it's a very big school. And so being Alberta, the alligator being the mascot, I mean, you could be on the field in front of 80,000 fans. You could be on the front and the field in front of millions of people on TV.

So there I think that that is, similarity to content marketing, to marketing, to kind of being out there. But you also, I would imagine, have to do one on one deal with a lot of people, maybe children, maybe drunk frat guys, I don't know.

Val Riley: I would say two big lessons came out of that. So yeah, so number one is sometimes if, if the, if the if the game is really good, the fans don't care about you. Right. And what that means is like, if the game is tight, everybody is really hyper focused on the game, and you could be doing the craziest antics on the sidelines and no one's paying attention.

And I think that that's a good lesson for marketing, because sometimes, no matter how good you are, right, it's just you're not you're not going to reach the audience. So like you put out a press release and on the same day that something giant happens, like there's a big slack outage, you know, your press release is not going to get picked up.

It wasn't anything you did wrong. It's just sometimes the the audience isn't paying attention to you. And so I think that was a good lesson, like literally on the field, you know, cut your losses, go in. And then when it's a blowout, boy, everybody wants to see Alberta every all the little children that people pass, see their babies and be like, here, hold my baby while I take a picture.

Meanwhile, by the way, we can't see. I'm holding your baby. And all I see is, like, straight ahead. So very, very, nerve wracking. But the other huge takeaway, from being a mascot or from, like, any crazy job you may have had before your professional career started, is it is the number one conversation starter in an interview?

Every single job I've ever had. So people will start the interview and they'll say, you were a college mascot. Tell me about that. It's it's an icebreaker. It's a way you people can relate to you. It's I always have a funny story. It was it. It's something that is a great way to begin any sort of conversation on any sort of job interview.

So I look back at it and it was only I only did it for a little over a year, but it has helped me throughout my career because it is it's just the number one icebreaker. It's such a great way to start a conversation with anyone, and people who are into college sports people are into professional sports, people that even aren't into sports.

Everybody has a question about walking around in a giant fur suit. So super easy to to make a connection.

Daniel Burstein: I love that. And also talking about reflecting your career, I wanted to ask you, you have had, a long and prosperous career. It's worked well, and I think you've done it the entire time. We mentioned university of Florida in Gainesville, Florida, and I wonder if there's any specific lesson you learned from that. And I ask you because, I remember my first agent I started here in, in Jacksonville, we had a big sign up on the wall and it said, to hell with New York, because marketing and advertising, this industry new York, San Francisco, I mean, maybe now you can say Boston, Chicago, Austin, there's some other cities.

It was a very concentrated in a few specific megalopolis. It's at least here in the United States, and I'm sure in other countries as well. And, you know, in my time in and obviously things have changed where remote work has become more common. I mean, I started remote work in like 2004 and have gone back and forth to remote and in person.

But, you know, it used to be a thing of like, you needed to be where the action is. You need to be one of those key cities and make sure it's happening. So I'm sure there's a lot of other people listening that might prefer a lifestyle somewhere else. Gainesville's a lovely city. There's a lot of other, you know, small towns.

I shouldn't even say city, maybe town that that people live in. Remote work. Yes. It has grown in the past few years. But did you learn anything from kind of building a career in this town? That that we can learn from?

Val Riley: Yeah. I will say early on in Gainesville is is a fairly small city. There's a big concentration of academia and health care. And I had a fascination with tech. And pretty early on I thought, I'm going to have to if I want to stay here and build my career here, I'm going to have to either switch to academia or get somehow involved in in medical, because there is a lot of medical centers here.

I like hospital PR, and I just in my heart, I really just didn't want to do that. And so I held strong. I went to work in economic development and this economic development organization was focused on tech companies. And so that's where I finally started to see the number of small tech companies that were in Gainesville. And I was like, oh, hallelujah.

Like, there's something here. And it was small and there weren't a ton of them, but I was able to make connections in the tech community and stay with the field that I wanted, and then eventually just work for software companies here in Gainesville. So, I almost gave up hope because the proliferation of, of tech companies in a small town, a small southern town, not so great, but I was able to find what I was looking for.

If I if I just made those connections and looked hard enough. So I would say, hold on to what you really feel passionate for, because you can find it. Certainly not the scale of New York. It's certainly not the scale of the Bay area. But you can find it. And then, as you mentioned, with remote work, you know, the company I work for now, the original company I was hired for is in the Bay area.

So they, you know, I interviewed and got got the job completely remotely. And the company ended up during the pandemic going 100% remote distributed workforce. So, I feel like in the end, it paid off that I stuck to my guns. And I did get the quality of life that I wanted being in a small city. So I really do think it's possible now, but I would say if your passion is somewhere you can find it, it might not be the scale that you're looking for, but I really believe you can find it if you stick to it.

Daniel Burstein: So in a small city and just even in an industry, a lot of times your reputation precedes you. And so it's really important to make sure you've got the reputation out there that you want to represent you. And so I really like your your last lesson here. Kind of heartwarming. But I like like it. That is true.

Nice people still win. Like I, I got to imagine that's really important for being a small town. But just in any industry. You said you learned this from CMO Chip House. So how did you learn this? And how can you convince us that this isn't just something we want to feel like? It's true. That is actually true.

Val Riley: So, Chip was the CMO at Insightly and he was like the quintessential midwesterner. And, like, I had always heard that Midwestern people were nice, but holy cow. Like, if he wasn't the nicest person and, you know, as CMO, it's it's a difficult role here, you know, I'm feeling it now, just in my role. It's, you know, there's never enough leads and never enough quality.

There's never enough quantity. You know that kind of get beaten down by the sales team and, you know, the budget's never enough, and you're always shoe stringing stuff together and trying new things, and some things fail and some things don't. And he never cease to have a positive attitude. He and he never was, one to blame other teams or or place fault with individuals or their efforts.

He was just like, we're just going to keep on going. We're just going to stay positive. We're going to keep on going. So he was the CMO at Sharp Spring, which was where I worked previously, and then we worked together at Insightly and just two high pressure environments, and he just never became a jerk. And I was like, there's a lesson.

There's a lesson there for sure. I mean, I'm a New Yorker and so at heart and so I feel like I can very easily go down that path of, you know, being having a New Yorker attitude. And I think Chip just taught me that, that, you know, being kind, being nice, that's the way to get the most out of people.

And, and, you know, you can still be a kind person and really be an effective marketing leader.

Daniel Burstein: So I love hearing that. But I also wonder how that applies to how we treat our customers, because one of the things you said about Chip is he was able to deliver feedback in a supportive way. So when you have to deliver feedback to customers or potential customers, sometimes you have to show them there's a pain point.

Is there anything you've learned and how to do that in a kind of positive and supportive way? Because for us, for example, one thing that's work, because, you know, I'll get these messages like your website sucks or SEO sucks, this is horrible. And I'm thinking like, that's the first relationship you want with me as a potential customer. You're going to insult me like you might be, right?

But that's that's your foot in the door. Right? And so one thing we've done as a company that's worked well is, as I mentioned, we have live events. And so we would run these contests right where we would get like a nonprofit or maybe a sponsor and be like, okay, we're going to test our landing page or test or email or something.

And we would get the whole audience involved in doing it to see what won. Right? So we we work together to create some hypotheses with the audience. We actually test them during the event, and then they would see the results by the end of the event. And this did two things that was really helpful. One, it removed their brand from it.

Right? Because when it's your own brand, you can be defensive. Like, what do you mean? I worked so hard on this. I remember starting at a position and I came in. I came in badly because I was saying everything that was wrong. And then someone pulled me aside and like, you know, all this stuff is wrong. But we worked really hard to get it this wrong.

It was way wrong. Or before right. That's one thing. But the other thing is also we took them on the journey, right? It wasn't just day one of the event. First five minutes, like, you guys are horrible and don't know about landing page optimization, right? It was like, okay, here's our goal. Let's work together on it. And then as they work through the journey, they realize, oh, I wish I knew this better or that better that, you know.

So by the time you get to the end, you've got a real world test. It's like, okay, now there's an openness in them. They got that feedback. Hopefully we were nice people to do it. They got the feedback, I want to learn more and I want to improve here. Right. So for you, Val, a a pain point, we all know it's an important in to a customer.

Some companies use FUD fear, uncertainty, doubt right. They kind of come up with these negative ways. Have you found to be like still a nice person, a nice brand, but to start getting across to the customer, hey, there's a pain point. There's there's a place you need to improve here.

Val Riley: Yeah I would say we had a recent instance where there was some tough love. So our CRM had a freemium which was an extremely generous freemium. You can have two users like tons of storage free for in perpetuity. And the idea was as you grow as a company, you, you know, need, more seats, more powerful CRM that you would stick with insightly and and grow with us.

But I think it ended up being a little too generous. And so we decided as a company, we're going to end this free program, and we're going to offer to move folks to a paid account. And we gave them a long period of time where they could decide to upgrade or not. And, and honestly, like people who had used our free CRM for seven, eight, nine years never paid us a penny.

And we're just so like, just had the audacity for them to say like, hey, this absolutely should still be free forever. I was just like, okay, so let's just kind of shocking, like again, like the audacity. And so we had this whole communications plan and with this whole rollout and we gave them this very generous coupon code and we're like, hey, we'd like for you to stay with us or whatever.

But just dealing with those folks, during that process really taught us a lot. Like, you know, this is a mission critical piece of software. The CRM is and these people were relying on it, and now we have switched it up on them. So how can we have grace for this change while also moving them in the direction we need them to move, either convert to a paid customer or decide, hey, I'm going to take my business elsewhere.

Like those are both fine outcomes. And so in the end, we ended up converting a pretty high percentage of folks to a paid account. But having the grace during that time period for people who were just so upset that, you know, again, like this gravy train had come into the station a little bit, I think that there were some good lessons there in understanding the customer and putting yourself in the position of the customer and trying to advocate for them as much as you could while still having the goals of the company in mind.

Daniel Burstein: Yeah, I think that's a kind of nice summation of what it is to be a marketer advocate for the customer, but to have the goals of the company in mind. Which brings up my final question is, okay, what are the key qualities of an effective marketer? Val?

Val Riley: So in my opinion, if you are going to have a career in marketing, you have got to commit to always be learning. If you are someone who wants to learn a skill set and then sit back and just rinse and repeat for the rest of your career, you can find a lot of great things to do. I, you know, but marketing is not one of them.

You know, every week, every month there's new technology, there are new acronyms, there's new strategies, there's new philosophies. I personally listen to multiple marketing podcasts. I subscribe to multiple marketing newsletters. And still sometimes I'll log in or I'll see something and I'll be like, gosh, I don't know what that is. And it's just it requires a lot of time outside of your day to day work to just stay abreast of what's happening in the market, what's happening in technology, how is this career continuing to evolve?

So if you're not interested in doing that, this isn't that the career for you? But if you are a lifelong learner, I think that's the number one quality for an effective marketer.

Daniel Burstein: That's great. And hopefully everyone listening gets multiple, we don't care what the other ones are, but how I made it a marketing podcast for marketing. The marketing company is like, this is the one you should be listening to.

Val Riley: So all the above, right?

Daniel Burstein: Anyway, thanks so much for your time. Val is a real pleasure. I learned a lot.

Val Riley: Thanks so much for having me. This was great and it's always nice to meet a fellow Gator.

Daniel Burstein: Thanks to everyone for listening.

Outro: Thank you for joining us for how I made it and marketing with Daniel Burstein. Now that you've got an inspiration for transforming yourself as a marketer, get some ideas for your next marketing campaign. From Marketing Sherpas extensive library of free case studies at Marketing sherpa.com. That's marketing rpa.com and.