On this episode of The Founder's Sandbox, Brenda McCabe sits down with Jen Apy, Area Managing Partner and Chief Marketing Officer at Chief Outsiders, to explore how scaling companies can unlock growth through fractional marketing leadership. Jen shares insights from her 30+ years of marketing experience—spanning Mattel, Adobe, Intuit, and now Chief Outsiders—and introduces listeners to the Growth Gears framework: a strategic methodology designed to help small and mid-sized companies grow efficiently and sustainably. Jen and Brenda also dive into key trends such as the rise of "flash teams," how AI is transforming the marketing playbook, and the importance of being a learning organization in a fast-moving world. You can find out more at https://www.chiefoutsiders.com on Linked in https://www.linkedin.com/in/jenapy/ or the chief outsiders leadership page https://www.chiefoutsiders.com/leadership-team and find the Growth Gears assessment here: https://s.chiefoutsiders.com/growth-gears-score?cf3=japy@chiefoutsiders.com transcript: 00:04 So welcome back to the Founder's Sandbox. I am Brenda McCabe, the host of this monthly podcast where I am joined by business owners, founders, and professional service providers that are scaling businesses. 00:34 with great corporate governance. This podcast is now in its fourth season and very excited to have Jen Apy as my guest today. For those that are subscribed to the Founder Sandbox, you always know that we have a story that's going to be told about the origins of the company and the founder and the professional's experience as the introduction here. And we will always come back to the... 01:02 the sandbox where we're talking about resilience, purpose-driven and scalable growth. And when Jen, who I've known now for several years, we work in the same ecosystem, spoke to me about the growth gears, that is kind of the overarching framework of chief outsiders. I was fascinated and wanted to offer the platform of the podcast to get the message out to business owners that are 01:30 scaling and have not yet thought about using fractional marketing services. So welcome, Jen, to this fourth season. um Absolutely delighted to have you here. Oh, I'm delighted to be here. Excellent. So we did choose a title. We're gonna you're gonna hear the word growth gears throughout this podcast. So the title for the podcast today is growth gears for scaling. And 01:56 Jen and I kind of share a similar background in the sense that we've been out there over three decades. I um had my own consulting business. I worked in the McKinsey & Company and reinvented myself uh around really bringing the expertise that I had at multinationals into the ecosystem of growth stage companies. Jen, tell me you are multifaceted marketing professional over three decades. 02:26 of experience contributing to marketing excellence. Tell us a bit about your origin and your currently, I think since five years ago, the area managing partner and chief marketing officer of Chief Outsiders. So share a bit how your role has evolved and what's it like to be with this company that was once a startup itself. Well, thank you so much for having me, Brenda. It's been a wild ride. 02:56 I feel like I was so lucky early in my career to work with fabulous marketers at Mattel and Intuit and Adobe. And now to have the opportunity to apply those skills to help small to mid-sized companies grow. It's really been a fantastic experience. I feel like this is my purpose. Oh, beautiful. To share these enterprise little marketing skills with smaller companies that 03:25 are hungry for growth. you when I, when I meet founders or I meet CEOs, I'm always really curious about, know, what's working, what's not working. You know, how do we create this flywheel that can help them grow in scale? It really is, is something I enjoy. You know, you found your purpose and then I guess your purpose found you working with chief outsiders because you were also a solopreneur for years. What would be your 03:54 tagline if if anybody were to just listen to five minutes of the founder sandbox, what would be. Jen appease tagline such a good question. I think it would be be something like committed to growth. I feel like that is my purpose. That's what I enjoy. And you know now it's part of outsiders. I I now have 125 colleagues who feel the same way. They've all been fortune 1000. 04:23 and larger company marketers from a variety of different industries. think collectively we've probably covered over 80 industries, over 5,000 engagements. I mean, it's just incredible that the people at Cheap Outsiders that I get to work with every day. And I do feel like commitment to growth is almost a shared purpose for all of us. That's why we're here, because we love to make an impact, to see that impact on smaller companies and be a part. 04:52 of their leadership team. We say that we're outsiders, but we're really embedded as insiders and therefore we can have that impact on companies and watch them grow in scale. It's very gratifying as a marketer. m I also work in the small and medium sized enterprise area. And last month I actually wrote a blog on enterprise, forms of enterprise and the like. 05:18 Did some research on actually SMEs. How many SMEs in your estimation actually reach or go beyond $10 million in revenues? SMEs are 47%, I believe, for the number of enterprises in the United States. But how many actually scale beyond the $10 million revenue? You know, it's a surprisingly small number, like maybe less than 1%. But you know, that's why we're here. 05:47 We want to increase the chances that those companies can scale, you know, 10 million, 50 million, 100 million. We believe that by really applying the market insights, customer insights, competitive insights into, you know, the strategies around positioning and offers and target marketing will lead to the cost of 06:14 efficient and cost effective strategies and execution that will help companies scale. that really is the heart of the growth gears methodology and approach. Well, that's a great segue. You and I met at the recurring revenue conference, I guess, in the seventh year. And as you walk me through the growth gears, you also have an assessment tool. Would you like to share? 06:42 overarching what is what are the gears, the growth gears, what are the key aspects that one can be surveyed about and then and how to engage with the chief outsiders, because I found it fascinating. And I actually used it with one or two of my clients to kind of get the wheels, no pun intended, right to to start moving, right? 07:12 Yes, so the assessment that we use asks companies and leaders questions about the business, about how much do they know about their customers, their competitors, the company, they looked at market trends? And then starts to ask about, do they know where their revenue comes from, where their growth is gonna come from? they understand what channels are most efficient and are they measuring uh the effectiveness of the marketing? 07:41 programs that they have in motion. And it's not every single question that we could ask, but just enough to get them thinking about where growth is gonna come from. And so we use this assessment, usually around this time actually, we're getting close to Q4. And we use it about this time in order to help them think ahead in terms of what are the priorities that are needed for the following year in order to stimulate. 08:08 enable or actualize growth. So if anyone's interested in doing this assessment with me, it's free. Just, you know, reach out to me on LinkedIn, happy to provide you with the link and then have a conversation about what the answers mean. Absolutely. Jen, we'll put those, the survey or the assessment, pardon me, in the show notes. All right. Great. In addition to other areas. So talk to me a little bit about Chief Outsiders. You did say it was a startup at one time. 08:37 How long has it been around? What's the organization look like? And what are the challenges that you particularly are dealing with with the advent of AI? That's a very little question. That's a great question, though. But Chief Outsiders has been around for over 10 years. I think we've been around before the term fractional executive or fractional marketer was even a term. think 09:01 Maybe early on we might've been discussed as strategic business consultants, right? Because we're helping companies grow in scale. But we've been around for over 10 years. We've been on the Fortune 5000 for quite a few years. I think definitely 10 or more. the way that we've grown is by really focusing on what marketing leadership needs to do. 09:30 for companies, which at the end of the day, it's about knowing who your customers are, where to find them, and then how to grow the company based on that focus on finding and retaining customers, whether it's increasing market penetration within a certain target segment or finding new markets or launching new products, whatever that growth strategy is, how to harness that and help 10:00 a company, um, scale over time and marketing has changed so much. I know over the years, mean, I've seen that with your companies is overwhelming. I pardon. I will get back to the question, but I, many, many years ago, McKinsey, was a marketing expert research. We didn't have all these amazing tools we have today to conjoin analysis, you know, with your Excel sheets, right. And focus groups. 10:29 Right. So the sophistication, channel, you know, growth explosion is, you know, I threw my talent a long time ago. Well, you know, it used to be, you know, direct mail and then websites, right. And then e-commerce and, and then it was about social media and content marketing and then SEO. I mean, it's just daunting. And now we have to be thinking about AI in all facets of the 10:59 the marketing toolkit, right? It's impacting every aspect of what we do as marketers. And we have to be thinking about AEO, like answer engine optimization in addition to SEO. So it really is rather overwhelming. So I think that over the years, Chief Outsiders has recognized that the marketing tactics and strategies are going to change and we need to change with it. But that the focus on 11:27 growth is going to come from really the growth gears, right? The approach to understanding the market, understanding how to go to market, understanding how to execute cost effectively. So recently in the advent of AI, knowing that it was going to impact so much of the marketing mix, we actually started to develop an AI platform for us to use. Yes, for us to use internally. What it does is confidentially, 11:57 takes all of the insights for all of the engagements that we've done with companies so that when we are working with clients, we can benefit from that collective knowledge and be able to deliver better, deeper, faster insights from day one for our clients. So deeper insights, proven strategies, best practice execution. There isn't a workstream for marketing sales that isn't going to be impacted by AI. 12:25 So we've definitely thought about that and made sure that we can leverage all this knowledge in order to help us be better marketers for our clients. That's fascinating. It's kind of scary, right? So you've basically like in the healthcare industry, you've anonymized, right? The plethora of data, right? Within the walls of 12:54 chief outsiders of the 10 years of experience and I don't know how many clients, right? To then really document and have your own, for lack of another word, I guess, is it? The knowledge base. The knowledge base, but it's kind of an ocean, right? Data ocean. Yeah. And, you know, and this is how the AI tools work. 13:19 We figured we might as well have something that we can use on a proprietary basis and that can help us not only create our deliverables and have better deliverables, but also to help us manage processes. Because as we talked about with marketing, there's just so much going on, so much to consider, so much to do. This AI platform also helps us to manage those processes. And one of the things we haven't talked about yet is fractional resources. 13:47 I believe really are the future of work. And that's one of the reasons why I'm so excited to be a part of Chief Outsiders because we believe that as well. And that's also part of the reason why we built this platform. Right. So one thing that I want to highlight just from the last discussion here is 14:08 AEO rather than SEO or in addition to SEO that I mean, heard it here on the founder sandbox. Not only do we have to be looking to have our SEO optimization, it's AEO optimization. Yes. So answer engine optimization. And that's coming of course, from the AI tools. You know, I think the stat is something like 70, 71 % of searchers, anyone searching. 14:37 They're now using the AI engines instead of, or sometimes in addition to regular search. But it's the reason why Google is losing traffic share, right? Because people are going to these AI engines sometimes exclusively for certain things. And so this has had an impact on marketing in a couple of ways. One is we need to now optimize our content for answer engines, which it's not that much different from SEO. We still have to adopt the same good. 15:06 SEO practices, you keywords, relevance, backlinks, things like that. But now we call it LL or large language model optimization in 2025. uh In order to be able to rank in those answer engines, we need to also consider brand strength and authority, oh citations, quality of content, sentiment. You know, we really 15:35 PR from authoritative sources is really going to become more important. And so we do a lot of testing ourselves in terms of how Chief Outsiders ranks in these engines. I was going to ask you, have you done that? Yes. And that's how we know that it's not just the SEO good practices that's helping to rank in answer engines. um 16:02 It's also these other things, brand strength and authority. The content needs to answer questions. these engines are understanding when content is authoritatively answering a question. And there's so many factors involved in figuring that out. There are a number of tools we use to see how we're ranking. There are a number of tools we use to figure out how we're 16:33 uh how we're able to, uh I guess, for lack of better words, out the competition, right? And score, right? In our content. And we use this knowledge of how it's working for us to help our clients as well. And we've been doing this from the beginning because we were very aware of all the changes. um So you have your own growth gears operating system. 17:00 It's a remote working AI enabled platform, right? That also enables remote and hybrid teams that come together. Speak to me a little bit about that. GrowthGear's operating system is effectively your LM? Yeah, that's the, well, that's the AI platform that we developed is called the GrowthGear's operating system. And so not only does it leverage the best content, the best tools, but because of the way that we're designing it and it's really to support us, right? And how we work. 17:29 we are really enabling fractional resources and remote and hybrid teams to work together effectively on the projects, the marketing, the growth plans that companies need to scale. this is kind of the way, I mean, if we believe that fractional resources are of economic benefit to both companies because they don't have to hire 17:56 A lot, you know, heavy talent, right for long term. They can hire just what they need when they need it. And also as they evolve and grow, they might need different resources, right? So they can they can cycle through the skill sets they need, but but also because there's economic value because workers, if they want to be more flexible, if they want to leverage a specific skill set and not necessarily be tied to one company gives them the freedom and flexibility to. So I think for for both reasons, there's there's a lot of. uh 18:26 momentum toward this style of working. the platform that we have, you know, it can enable these operational fractional resources, not only marketing, but any part of the organization in the future. Let's go. Let's take that idea or what you're observing in the market and actual client work a little bit further. So how would a potential client 18:54 engage with chief outsiders. They're at, you know, 3 million AR, they have not yet hired a marketing full time, right? How, what would would walk us through a typical, for lack of another word, engagement, or how do they engage with chief outsiders? And particularly, the second part of that is, if you're talking about 19:21 Flash teams, I think is the term that you and I discussed, right? Yeah, it's actually the title of a book being launched by a professor from Stanford, Melissa Valentine. She's coined this phrase flash teams, which essentially is what cheap outsiders does, right? We pull together the resources that a company needs at that moment in time in order to solve their growth problems. we're essentially a flash team enabled by 19:51 the growth gears operating system. Cool. So I'm not I'm the CEO. I've got to hit some revenue milestones. I've interviewed some candidates. I'm not yet sold for you know, bringing in full time, full time chief marketing officer. Jen gives me a call. How do I how do you how do I engage with you? Yeah, well, the first thing I want to understand is, is what what keeps you up at night? 20:21 Right? What, what are some of your growth challenges that, you're struggling with? Because the first thing I want to do is really understand, you know, what resources do you need at this moment in time in order to get you from A to B? so oftentimes we'll look at this and say, is this, is this going to be solved by a marketing led team or sales led team? Sometimes that's the first thing that we're thinking about. And then how much do we know already about the situation in terms of. 20:49 customers, competitors, market insights, customer buying journey, channels that are working and not working. We're wanna know all of that so that we can figure out the most efficient way to approach solving those growth challenges and what work streams are needed. So we'll bring in a fractional executive that's a good fit for that company and then orchestrate the resources that are required to get to the next step. And then when that engagement is through, 21:18 we'll figure out what the next level is. Maybe the next level is bringing in full-time permanent resources to help execute and to help scale where we paid ourselves out of the picture. Or maybe it's just dialing back to more of an advisory role and then bringing in fractional resources from different places in order to be able to test and scale and see what's going to work, what's going to land before we orchestrate on a more. 21:48 So we're very flexible with what a company needs at any point in time. And no two companies are alike. You when you're a $3 million company, you might have talent and skills and gaps that are different from the last client that we had. And we know that. We can recognize those situations just because we've had so much experience working with so many different companies. We can very quickly figure out what's needed for the next step and just give a company exactly what it needs. 22:16 to it. You do tap into your, your network of your 125 professionals with them, know, goodness, the years of experience that you all have obtained while at fortune 1000 companies. Amazing. Oftentimes, I've seen you with as keynote speaker, you do give conference speak and you speak at conferences. What one of the most recent 22:42 conferences. I'm not uncertain where it was, but you the topic you spoke to, Jen, was winning website traffic in the age of AI, what CEOs need to know? Can you without sending us to you know, that I don't know whether it's on online, we can put that in the show notes. But what's the top, you know, line messages from that conference where you spoke about winning website traffic? Yeah. 23:10 Well, I did it with a couple of my colleagues who are very experienced in digital transformation and now how to win traffic with the answer engines. And so we talked about some of the uh tactics that we're finding work nowadays and how that's going to change how companies need to think about orchestrating their marketing mix. So Mike. 23:36 Colin Angela gave an example of a very specific example of an article that had been written for SEO that now needs to be written for AEO just so that people could see the difference. But I think the main message that we were trying to send uh to companies is uh marketing is not static. Just because you've figured out your marketing mix doesn't mean it's going to work two years down the line. It's constantly evolving. And so you need leadership. 24:04 who can be thinking about how are customer behaviors changing? How do I reach them differently? And the fact that 71 % of searchers are going to answer engines, that's a huge shift and marketers need to be ready to address that. So if you're a smaller company and you just don't have the resources to keep retraining your staff. 24:29 every year or so and you need that expertise in the know how do I compete now today? How do I set myself up for success? That's where we as Fractional Resources can come in and help you be that learning organization, that resilient organization that's going to survive through the next sea of change. 24:51 That is fascinating. Yeah, it's it's a living beast, right? marketing and it's moving so rapidly, it would be hard. I'm to actually have the inside resources, the talent inside unless they're constantly being retooled. So it is an opportunity to use fractional resources, depth of expertise that you have. Yeah. And that's one thing that I value about the chief outsiders culture is the fact that I think what's made us 25:21 so resilient is the fact that we're really a learning and sharing organization. We've recognized that change happens rapidly. To be resilient, we need to change and constantly be learning and retooling ourselves. And that is something we highly value. But to be able to do that quickly, no one person can do all this on their own. It's nearly impossible and very overwhelming. You can't do it in a silo. So we have a culture of sharing where 25:50 If we learn something new, um we'll share with the rest of the organization. So that, that, uh, that webinar that we did was just as much for us and our executives as it was for the clients that we, that we serve in this culture of sharing really creates resiliency in the sense that if, a company brings in one of our fractional executives and let's say they encounter a market challenge or a sales challenge that that particular 26:19 executive hasn't seen before, they can turn to the other 125 marketers and say, hey, let's get together. Let's put our best brains on this business and determine what things we might be able to try or what things we should put in place in order to benefit this organization. And I think there's no individual fractional out there that has access to that much talent and expertise. 26:49 on a moment's notice as we do. And that's part of what's going to create the resiliency that we need as an organization to survive in the next decade, because everything is just going to start to move faster and companies are going to just need that much more speed. So, but we also believe that's a value that we can bring in addition to being interim and not being full-time and bringing in the expertise they need to write at that moment. We can also draw on the collective expertise of the tribe. So the brain trust. 27:19 Well, that's a good term. love that. Right. Brain trust. I love that brain trust. One technical question of the 125 professionals within chief outsiders and interim roles. Is it solely in the marketing area or do you also offer maybe in the sales? there other interim roles? That's a really good question. So we do focus on marketing and sales primarily, but sometimes we're actually brought in as fractional COOs. 27:49 as well or division heads. And it's because of our broad leadership expertise. And some of our executives have been CEOs of their own companies. They founded companies, they've sold companies. So they do have that broader business perspective, but primarily it's marketing and sales. Excellent. We're going to switch gears, to the standby. No pun intended. 28:17 That's right. That's here in the founder sandbox. I'm passionate about building resilience, scalable and purpose-driven companies. And I like to ask my guests briefly, what is the meaning of resilience? What does that mean to you? Or does he chief outsiders? It's a fascinating part of the podcast for me become that you have very different definitions. And that's the beauty of asking this. Yeah. Well, I think that resilience, at least for for me, for us, a chief outsiders means 28:46 being able to survive and move forward and grow in the face of massive change. Right. It's not, it's not bending to the will of the market. It's, it's, it's basically saying, you know what? We know how we can add value at this moment in time. And we have the tools to address this change and add value. that, you know, it is one of the reasons why we constantly are thinking about 29:15 how do we bring more to the table for our clients? So in addition to the growth years operating system that we created, we also have an ecosystem called team outsiders of fractional marketing execution resources that we can draw on at any point in time and create our own flash teams for our clients. So let's say we've gone through the strategy and we've determined that we really need an e-commerce expert 29:45 that can optimize Amazon or we really need somebody who can take charge of developing the content that's going to address not only SEO and or but also AEO and we'll draw from our pool of team outsiders resources and we'll put together that fractional team for the client at a moment's notice. So we believe that that is going to make us a lot more agile. 30:13 for our clients because sometimes they just need to get started, but they don't have time to go higher or they don't have time to go evaluate a new agency. We can bring somebody in. We can, we can set the stage. We can get things going and then let them have the time to decide really who they want on a longer term basis. So, you know, agile teams, flash teams, it comes from our ability to be able to, draw on this network of. 30:42 team outsiders and to be resilient. How about purpose? What's purpose mean to you? Purpose. You know, I think that when I look back on my career and also what I'm doing here at Chief Outsiders, I get the most satisfaction from seeing smaller companies grow from helping founders make their dreams come true. You know, there are so many great companies out there. 31:12 that just need a shot at the big time, right? And we can do that because we've seen it. We know how to get a company from one to a hundred. We've seen it. We know what a company at one or a company at zero, what they're faced with from the standpoint of challenges, time, resources, focus, right? And so we can adjust what we do in order to adapt to that environment. But we know what an organization is going to need 31:41 to be competitive and to need to grow at 30, 50, 100. And we can keep our sights on what that needs to be and advise the companies we're working with on how they're gonna get there. So yes, we're implementing this today, but it's gonna look like this tomorrow, but we're not ready for that yet. We're just gonna do this here today because you don't have the time or the bandwidth or the money to do that many things. But this is, we've done the analysis, we've done the research, we've done the testing. 32:11 This is what you need to scale for right now. So, you know, being able to do that and then see these companies grow from 10 to 30 to 50 million, it's a thrill. it is very, very rewarding. So I think that, you know, I found my purpose and this is the, in speaking with my colleagues, they're all, we're all here for the same reason. So we really do have that shared. 32:39 purpose and we really enjoy what we do. Fantastic last one and then we'll move to how to contact you scalable growth. I'm certain you're going to talk about those the growth gears, but what's scalable right? What's that mean to you? Scalable growth to me means we figured out what works and we can replicate it cost efficiently and cost effectively. So that is 33:07 our focus when we're working within the growth gears methodology, we're looking for the way to scale most cost-efficiently effectively. I know that one of the things that you are really big on with your companies, the companies you invest in is governance. Yes. You're really big on governance. And when I think about governance, I think about responsibility and accountability. And what that means to me as a marketer, 33:35 And as a revenue leader is making sure that the spend that we commit to in marketing and sales is going to drive revenue and growth cost effectively. so by making sure that we've done the analysis, that we figured out what's going to work, that we've tested before we scale is that responsible governance approach, right? To marketing and so 34:05 You know, I think that there are some companies that are in situations where they have to scale no matter what. They just throw money at it, you know, scale no matter what. And there are situations where that needs to happen. But we find with the companies that we work with that the more responsible, prudent, accountable, you know, organic growth is what the founders are looking for. And we know how to do that. 34:35 Replicable, right? Replicable, yes. Amazing. So Jen, um last question before we listen to how to contact you. you have fun today in the Founder's Sandbox? Oh, it's always a pleasure to talk with you, Brenda. I really enjoy our conversations. We're of like minds. That's true. That's true. Avid readers and bringing the best to our clients. So thank you. How can my listeners 35:04 find you and best reach chief outsiders. Yes. So they can find me on Jenna, but they can also find me on the chief outsiders website on the leadership tab. And from the chief outsiders website, you can also learn about all of the things that we do. can meet all of the 125 executives that we have. You can learn more about growth gears, OS and team outsiders. Excellent. And 35:32 In the show notes, will provide the assessment so that you listeners that are actually considering, you know, what do I need to do at this last quarter of the year, right? To plan my marketing resources, just download the assessment. It's a very interesting tool. So thank you. Well, to my listeners, if you enjoyed this episode with Jen Appie of 35:56 chief outsiders. I'd encourage you to subscribe to this monthly podcast where we have founders, business owners, corporate board directors and professional service providers that are really building scalable, purpose driven and resilient companies with great corporate governance. Signing off for this month. Thank you for joining us here on the Founder's Sandbox.
