1703 – Court Avenue As Your Go-To Experts for Digital Strategy with Kenny Tomlin

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Co-Founde & Partner of CourtAvenue, Kenny Tomlin.

Court Avenue primarily works with Fortune 1000 companies and emerging challengers in the venture-backed and private equity-funded space. They offer various services, including managing and operating clients' digital presence, utilizing AI and emerging technologies for customer engagement, developing digital products and software, and optimizing platforms like Salesforce and Adobe.

Kenny shared that the industry has evolved significantly due to the rapid emergence of new technologies. This evolution presents both challenges and opportunities for their clients.

Court Avenue is known for its expertise in digital strategy, helping clients navigate the competitive landscape and improve their business by adopting emerging technologies. They also specialize in the shopper e-commerce category, assisting clients in succeeding in omnichannel retail, including online and in-store experiences.

Kenny believes digital transformation has a return on investment and can help companies operate more effectively and efficiently. He mentioned that Court Avenue is expanding globally, with an office in Latin America, and they are actively looking for new clients.

Key Points from the Episode:

  • Introduction of Kenny Tomlin, co-founder and partner of Court Avenue
  • Court Avenue's specialization in digital transformation and working with Fortune 1000 companies
  • Services offered by Court Avenue, including managing digital presence and utilizing AI for customer engagement
  • Court Avenue's expertise in digital strategy and helping clients navigate the competitive landscape
  • Focus on shopper e-commerce and assisting clients in omnichannel retail
  • Brands Court Avenue has worked with, such as General Mills and Dell
  • Growth and future plans of Court Avenue, including expansion globally and seeking new clients
  • Ideal client for Court Avenue, someone in the C-suite who recognizes the importance of digital transformation

About Kenny Tomlin:

Kenny Tomlin, a prominent figure in the digital transformation realm, boasts a remarkable career spanning over 20 years. Notably, he founded Rockfish, a pioneering digital innovation agency celebrated globally for seamlessly merging strategy, creativity, and technology. Under his guidance, Rockfish experienced explosive growth and was eventually acquired by WPP in 2011.

Tomlin's entrepreneurial spirit led him to co-found ventures in diverse sectors, including real estate (AnthemIQ), hospitality (Superstition and Frame Hotels), and immersive technology (Subvrsive).

His track record includes incubating award-winning software products like YouEarnedIt, acquired by Vista Equity in 2018. Currently, at CourtAvenue, he spearheads the product innovation lab and acquisitions, underscoring his enduring influence in shaping the digital landscape.

About CourtAvenue:

CourtAvenue, established in 2020, stands as a beacon of digital innovation crafted by a cadre of entrepreneurs, agency veterans, and business experts. This dynamic entity empowers some of the world's largest and most ambitious brands to expedite digital transformations. With a robust foundation rooted in expertise and entrepreneurial spirit, CourtAvenue catalyzes businesses aiming to navigate the complexities of the digital landscape.

By leveraging a wealth of industry knowledge and innovative strategies, the company facilitates seamless transitions into the digital realm for its clients. Embracing the challenges posed by the ever-evolving digital sphere, CourtAvenue emerges as a trusted partner, steering organizations toward success in the digital age and making significant strides in reshaping the future of businesses globally.

Tweetable Moments:

09:54 – “Building a great company is about relationships over time, which have huge compounding dividends.”

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Links Mentioned in this Episode:

Want to learn more? Check out CourtAvenue website at

Check out CourtAvenue on LinkedIn at

Check out CourtAvenue on Instagram at

Check out Kenny Tomlin on LinkedIn at

Check out Kenny Tomlin on Twitter at

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Josh (00:00:05) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach, or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my influence and click on podcast. We'd love to have you. With us right now. It's the co-founder and partner of Cort Avenue. It's Kenny Tomlin. Kenny, your website is Court Avenue. Kenny, thank you so much for joining us.

Kenny (00:01:09) - It's a pleasure to be here. Thanks for having me. Josh.

Josh (00:01:11) - Absolutely. Give us an overview of your work with Court Avenue.

Kenny (00:01:14) - Yeah. So Court Avenue works in that sort of broad category of digital transformation. We primarily support fortune 1000 customers, although we also work with some of what we call emerging challengers. Those tend to be like the venture backed, private equity funded businesses that are looking for technology partners. So the digital transformation sort of area that we primarily focus on is emerging technologies. And that expresses itself in, you know, evolution of e-commerce and shopper experience, digital products and platforms and just sort of customer engagement and marketing activities. So everything from, you know, managing and operating the digital presence of our clients. So customers like we we help partner with our internal teams. We built that site. We manage and operate that site for them to using AI and emerging technologies and how that can support clients customer engagement and workflows to digital products and software development, the martech stacks and supporting those and helping make sure customers at licensed products like Salesforce or Adobe or are getting the most use out of those platforms, etcetera. So it's a pretty broad category.

Kenny (00:02:27) - That industry has evolved significantly because emerging technologies are, you know, come at us so quickly and present a lot of new opportunities for our clients. And so we're one part strategy and consultative firm, and we're one part sort of execution and delivery firm. So not only do we support our clients with great ideas that they can execute to stay more competitive and more relevant, but we also have delivery teams that deliver against those ideas. So we're kind of full service end to end with our clients.

Josh (00:02:56) - In addition to key, which you mentioned, you've worked with General Mills, Dell, US Air Force, the US Air Force, Epson, among a number of other brands. When you begin work with a client, what are what are you typically seeing and what generally? And again, I know that these goals can be varied, but are there some general things that that you're well known for in terms of like if the outcome is X, then you really need to be working with Court Avenue.

Kenny (00:03:28) - Yeah. So I think, you know, this is the second company specifically that I founded in this space, as well as my co-founder and our third partners worked in this space as well.

Kenny (00:03:39) - So our team is pretty senior in terms of its experience, our leadership team and delivery teams. So I think first and foremost, like what we're really highly regarded for is our kind of digital strategy chops. So like making sense of all the opportunities and transitions that companies are faced with right. Because like I mentioned and you name some of the brands, these are incredible businesses. Many of have been around for many years. The competitive landscape for large companies in today's marketplace isn't just there. They're sort of large peers. Right. So Procter and Gamble is only competitor. Isn't Unilever as an example in today's marketplace, well funded, venture backed, private equity backed startups who from the ground up are built around emerging technologies, tend to be strong competitors. And that's why I think you've seen in the corporate America space a lot of R&D in buying a lot of M&A, I should say, in buying, you know, these venture funded startups because it helps them accelerate sort of their own agendas. So for us, I think first and foremost, it's kind of like helping them, helping our clients really have a strong plan for how these emerging technologies, one could impact their business from a competitive standpoint, but more importantly, improve their business.

Kenny (00:04:50) - Right. We're optimistic about technology. We think the technology gives our larger clients, in many cases, a competitive differentiator because they've got the resources to invest early. And so companies trust us to help them with that roadmap and that strategy. And then I think a category that we're in particularly well versed as that shopper ecommerce category. Again, we've got a long history and working in that space. And that's not just direct to consumer. That's not just, hey, building my e-commerce presence and helping me succeed online, although it is that but it's also digital retail channels like,, target, you know, the list goes on. But really helping our clients be successful and omnichannel retail. So what does digital mean in-store? But what does it also mean online? And how do you do a combined experience that that involves true omnichannel for our customers, which even even automotive like Kia. Right. Many customers, even though you don't buy your Kia at Kia, many customers decide what they want to buy.

Kenny (00:05:50) - What yeah, is they configure it and then they make that final decision in store. So how do you blend that online? Offline experience is a big part of what we do for our clients as well.

Josh (00:06:00) - Yeah, certainly. I can't imagine, you know, it's got to be a significant percentage that if someone if a consumer is decided that they are going to buy a new vehicle and you know, they have the opportunity to put all of that together, I'm really I bet that number's got to be really high. Total number of new car buyers who actually take advantage of that car building experience online. I want to know what my options are. I want to know what the total package or the total price is going to be before I go into a dealer. Those aren't decisions I'm going to make on the spot, but again, I'm probably biased to my own personality style, but that would be a great example of like, you know, meeting the demands of where consumers or your client's customers are and what their expectations.

Josh (00:06:50) - Is there a lot of consumer research that you do, or is that something that the client is already coming in to you with?

Kenny (00:06:57) - It is a partnership. In many cases, our clients aren't, in most cases naive to sort of that customer engagement experience and who their core demographic is. But there's so much data, right. And that's one of the you know, that's one of the sort of interesting times that we live in. And we're seeing that with our experiences using ChatGPT and other AI resources is like how much data has has aggregated over time and how that data can influence the customer journey and customer experience. So yeah, I mean, that's a regular like that is an ongoing challenge. That's not a point in time. And so we have a great data analytics practice. We have a great leader over that group. And a big part of what we do is looking at data and insights and analytics to really influence and inform future states. And that's an iterative process. That's not something you do once and you're good for three years.

Kenny (00:07:45) - That's something that should be a regular part of the wheel, the flywheel. And you should be looking at that and iterate in real time. And that's some of the exciting opportunities with with AI, right. Like we we're using technology that makes real time iterative changes to content, to ads, to, you know, your digital presence based on analytics and insights. And so it's well said. And I think, Josh, you're right. It's not just auto shoppers. It's you know, we work with Taylor Guitars, which is a smaller but iconic brand. You know people like to go online. They like to research their options. You walk into your local store and you know, even your local dealership. There's a limited selection of inventory that they might have on hand. And so doing that pre search, you know, looking online in advance that's a part like I think that's a regular part of consumer experience. And that's what we really emphasize to our clients. The like the like. We think digital innovation is defined by sort of three pillars speed, convenience and trust, transparency.

Kenny (00:08:47) - And if you think about your personal engagement, Josh, with like digital businesses that have been sort of transformative use Uber use Amazon, use Netflix, you know, the list goes on. You recognize that those were the three pillars that they checked all at one time. That's where combining digital and technology with consumer experience really check those three boxes simultaneously and was a difference maker for that industry. And so that trust transparency component of making sure your customers have access to the information they want, that it's available online, that it's easy to find. Again, AI helping significantly with this is a big part of building consumer trust between a brand and their customer. And so we really focus on that for our clients.

Josh (00:09:27) - And you're the co-founder of Court Avenue. And, you know, in just over three and a half years, you've managed to do some pretty significant work. How were you able to hit the ground running at such a high level, and be able to have the kind of impact that you've had in, you know, relatively short amount of time and also during, you know, a period of great disruption and upheaval.

Kenny (00:09:54) - Yeah, we started the company in January of 2020 and then of course March of 2020 Covid and we were small. We had very little overheads. So frankly, it was much easier for us to navigate than a larger company. And then and then Covid accelerated digital transformation. It exposed to a lot of companies weaknesses that they had in their digital ecosystem. So when everything moved from physical, in-person to digital and virtual, it created a lot of a lot of momentum for digital transformation because companies saw their where they were exposed and they recognized that they needed to accelerate their budgets in that. So from that perspective, it gave us some tailwinds in terms of our our fast growth. I would attribute that just to years of experience in network. I tell young entrepreneurs, you know, your network is more important than your net worth and building a great company, because sometimes when you're young, you're like, if I just had more money, I could grow faster. And the reality is, relationships over time have a huge compounding dividends.

Kenny (00:10:56) - And I mentioned that my co-founder and I both sold firms, so we built businesses in this same category. Mine was called rockfish. I started it in 2005. His was called Digital Aria. He started in early 2000 and we both sold those businesses. They were separate companies. We didn't know each other during that process, but we sold those to WPP. We're a part of that big global network. Our third partner in the company, Michael Stic, worked with me at rockfish, but then stayed on with WPP well beyond my tenure there and had a great global leadership position. So, you know, you just build trust and credibility and you never know, like this is an industry where like that director that you worked with 15 years ago today is the CMO or the CIO or the CEO. Right. And so building good relationships, building relationships of trust and credibility pay long term dividends. And with Court Avenue, so many of our relationships and kicking this company off became early clients. And, you know, I attribute a lot of our rapid growth to just that long history of trusted relationships.

Josh (00:11:56) - Your lips to God's ears on that. Kenny couldn't agree more with you. And you know, that is you know, people sometimes, you know, I've done over 1600 interviews here, and I cannot tell you how often among leaders that is the sentiment. And unfortunately, I think, you know, in a noisy entrepreneurial world that's not maybe communicated enough from some of the louder voices. But today, you know, Court Avenue is a company. I mean, according to LinkedIn, you're around or over 100 employees. Congratulations on that. What does growth look like over the next year or two?

Kenny (00:12:33) - So we're optimistic about growth partly because we have tier one clients that you mentioned. And we have a lot of room to grow with those clients. And as our capabilities expand, they do more with us. So we're in a bit of a, you know, build it and the opportunities will present themselves. And we're building based on what we're hearing from our clients. They they're asking us to build more capability.

Kenny (00:12:52) - And so a lot of our growth will come from continuing to mature existing relationships. But, you know, like we we started in 2020, we're still fairly under the radar as a brand. And business court Avenue is not a company that's gotten a lot of press or awareness because it is a very new company, and even some of the industry awards and recognition require three plus years of financial performance. ET cetera. You kind of got to really get through that validation phase of opening a business and starting it to say, okay, this thing's got some stickiness. It's going to be around. We don't want to jump the gun until you know and say, hey, Court Avenue is this great business and only for them to kind of implode. And so we're kind of moving into that next sort of operational phase of a company where we're starting to do better to in terms of telling our story. I mean, we we have grand goals and ambitions for this company. The people who we've hired are people who want to be a part of a growing organization.

Kenny (00:13:44) - They're excited about what they do. And and so we we're also going out looking for new clients to work with. And we're using our network to make introductions. I'm doing more interviews. Press et cetera. To create more awareness about who we are and what we're doing, because we believe we can compete with the best of the best. And we like our chances. We like, you know, our our portfolio of work speaks for itself. Now it's second to none in terms of quality and and and results. And so we are now in that sort of awareness phase of, okay, now let's start really telling our story. And so, you know, the economy is still questionable for companies like thankfully, you know, there's there's if you there's a lot of negative narrative related to the economy because negativity, you know, sells better than positivity in media. And and there are some unpredictable elements to the economy with the rising rates, etcetera. So there's a lot of companies that are still seeing pretty strong business, but sort of wondering if the if it's going to soften.

Kenny (00:14:43) - So like every company were navigating sort of a new, you know, economic circumstances that are in front of us all. But we're optimistic about it. You know, we think digital. Transformation actually has ROI all over it. We think it actually helps companies operate more effectively, more efficiently, and grow their business. And so even in a softer economy, that's where you want to make investments. If you're a company and and we think we're great partners to help companies kind of navigate through this. So we're expecting continued growth. Josh, we're also we opened an office in 2020 in Latin America. I was just there last week. Latam is actually booming. It's a you know, and we're in Mexico City, Argentina, Costa Rica right now and expanding in Latam. So we're also growing globally now. And and we're optimistic. But we recognize, you know, that it's you got to you got to hustle. You got to work hard. You got to give it every day and make phone calls. And and you know, we're still a small emerging challenger type company.

Kenny (00:15:39) - So we fight hard.

Josh (00:15:41) - Yeah. To our friend that's been listening to our conversation, they'd likely know someone that would be a really great introduction if not themselves. What does that profile look like? I mean, what are some of those things? If you define or describe who your ideal connection or ideal client like, not so much about who they are, but you know, kind of what they believe and what their values are. Yeah.

Kenny (00:16:04) - Yeah, that's a great question. Obviously, you know, you mentioned some of our clients earlier and it's diverse in terms of industry. We're working across insurance and technology and and you know automotive and health care and the list goes on. Right. And so we're not we're sort of industry agnostic. You know, our typical client tends to be kind of in the C-suite. So not that we don't work across the organization, but who brings us in. Might be a CMO, a CIO, a chief growth officer, chief digital officer, someone that has that sort of purview and responsibility for digital transformation, which is almost every C-level executive now in corporate America.

Kenny (00:16:43) - But we like we like working with companies that recognize the importance of making investments in digital transformation, that understand that. Marc Andreessen popularized that statement that software is eating the world. And in our opinion, almost virtually every company now is a software and a technology company. Right. Like, I don't care if you're in the consumer goods space or retail or what you do. There is a huge software sort of digital technology component to your business that you need to be making investments and leaning in on to maintain relevancy. So we like clients that sort of recognize that truth, that lean in and that want to be great partners, right? We we are. You know, when I was building rockfish and started it in 2005, digital transformation, like our customer, was a director level person and they almost outsourced all of it. Today, companies have built some pretty great capabilities in-house, but the need stay is larger than what most companies staff and can internalize. And they're looking for sort of boutique experts that can go deep in certain areas.

Kenny (00:17:46) - So we love partnering with great companies. We work well with our clients. We're a complement to their team, not a replacement in many cases. And so that's what we're looking for. Like every services company, you know like it's you want partnerships. You want collaboration. You want to look and operate like you're an extension of their team. And not just this vendor that you outsource to stuff too, because it's the things you don't want to do in-house or, you know, because there's some cost efficiency to outsourcing it. You want those customers that are looking for a good strategy, partners that can also deliver, that are hiring the best of the best talent, and work alongside your internal teams to really move the business forward. Those are the kind of profiles that we like, and probably almost every company would raise their hand and say, no, that's me, right? And so I get it that it's fairly cliche to say those things, but but that's that's who we love to work with. And so today, all of our client relationships have been very sticky and growing.

Kenny (00:18:42) - And I think I would describe the customer, the customers we work with exactly like that. So so more of that is what we would be looking for. And yeah, that's kind of how I'd addressed that question, I guess. Yeah.

Josh (00:18:56) - Kenny to our again to our friend that's listening. What is the next step. So someone that's been listening, maybe even part of their due diligence. They found this podcast and now they've been hearing our conversation. And what is that kind of those initial conversations or what what do you generally recommend people's first step be?

Kenny (00:19:15) - Well, clearly. I mean, these relationships can be long term when they're healthy and they start off by getting to know each other. And so a lot of our big engagements start as single projects and they grow from there. So a lot of our engagements start with a strategy assignment where they'll come to us with a specific challenge and say, hey, we're trying to figure out this, this challenge or how we think about this, and we'd love to engage Court Avenue to help provide a strategy engagement.

Kenny (00:19:42) - It's kind of we would compete more with a McKinsey, you might say, in that space. It's very consultative and strategic. And so that's where we'll start in many cases and then expand. But but it's also true that there are times like. Again, we've got a pretty good case study of work that we've done with clients like Kia and the Air Force, etcetera. So we get to know each other, we walk them through the work we're doing. We share with them how our relationship and partnership is structured with these key clients, and in many cases, they are looking for a full service, fully integrated partner. So it's not just a specific project, but they want like sometimes you might call it digital agency of record or digital transformation agency. They'll bring us in from depth. Step one with a very large retained relationship where we're building team to support their business together. So either are possible, but we're more than happy to start with a single project and get to know each other through that engagement and then grow the relationship from there as it makes sense.

Josh (00:20:37) - Now, your website, Court Avenue, what should they do when they get there?

Kenny (00:20:44) - So if they want to, if they want to talk about work together, they can go to the contact information. And there's just a quick contact form. You can email me direct Kenny at court Avenue as well, and I'm happy to connect that way. I'm also on social media, just my name Kenny Tomlin. So on Instagram particularly. But yeah, just if a company is listening and wants to learn more, just reach out to me, direct Kenny at Court Avenue and we'll schedule a call to get to know each other. But if they want to explore a little bit more, we're going to be launching a new website soon. You know, the the one challenge in our industry, it's the painter's dilemma, right? It's like we're so busy supporting our clients that our website gets a little dated, but we're we're very close to launching even a new version of that with some more information. There's a way to learn about us there.

Kenny (00:21:28) - We post a little bit on LinkedIn and other places as well, but just reaching out to me direct would be a great way to learn more about the company and talk about ways to work together.

Josh (00:21:36) - Yeah. By the way, I think your website looks perfectly fine.

Kenny (00:21:41) - It's not bad. It's just when you go, you know that there's a lot more, a lot more story we could be telling than our website tells right now. You think, man, I wish we had more time to keep it updated. But but we do and we are working on it. That's again part of that sort of operational phase that I alluded to earlier. As we've grown now, we're we're hiring more people to just focus on our own business and our own brand, telling our own story. And that's just kind of part of the evolution of this company.

Josh (00:22:04) - Fantastic. Again. Kenny Tomlin, co-founder and partner, Cort Avenue, your website, Cort Candy, thank you so much for this conversation.

Kenny (00:22:14) - Pleasure, Josh, thanks for taking the time.

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