705: Driving Business Success through Digital Evolution | Jen Swanson

Podcast Cover Image: Driving Business Success through Digital Evolution Featuring Jen Swanson
Podcast Cover Image: Driving Business Success through Digital Evolution Featuring Jen Swanson

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Curious about the transformative power of digital strategies in today’s business landscape? 

Tune in to unlock the secrets of digital transformation and evolution with Jen Swanson, a professional with over 25 years of experience in customer relationship management, marketing operations, and IT. Her journey spans influential roles in higher education and healthcare, contributing to organizations like the University of Minnesota, Capella University, Children’s Minnesota, and UnitedHealth Group.

In 2019, Jen ventured into consulting, later founding Tuckpoint Advisory Group in 2023. Explore the realms of Digital & Operating Model Transformation, C-Suite Advisory, and more with Jen at tuckpoint.com. Dive into a legacy case study at tuckpoint.com/legacy-case-study for a deeper understanding.

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Driving Business Success through Digital Evolution


Jeff Tomlin: Welcome to the Conquer Local Podcast! Our show features successful sales leaders, marketers, thought leaders and entrepreneurs who will inspire you with their success stories. Each episode is packed with practical strategies, as our guests share their secrets to achieving their dreams. Listen in to learn the highlights of their remarkable accomplishments and get tips to revamp, rework, and reimagine your business. Whether you’re a small business owner, a marketer, or aspiring entrepreneur, the Conquer Local Podcast is your ultimate guide to dominating your local market. Tune in now to take your business to the next level! 

I’m Jeff Tomlin and on this episode, we’re pleased to welcome Jen Swanson.

Jen is the Founder and CEO of Tuckpoint Advisory Group, a collective of digital transformation experts helping world-class organizations integrate digital technology into all areas of their business, to improve their operations and customer experiences. 

In 2023, over 70% of Fortune 500 companies have embraced digital transformation – from digitizing internal operations to leveraging cloud and AI capabilities and moving into digital-first consumer offerings. However, many companies stall out and never realize their ROI because they only focus on the tech, forgetting that organizations and their operating models have to evolve too.

Companies that work with Jen and Tuckpoint see a total transformation from the C-Suite all the way to the front line. In 2021, Jennifer was recognized as one of the Top Women in Business by the Minneapolis St. Paul Business Journal and Mentor of the Year by TeamWomen.

Get ready Conquerors for Jen Swanson coming up next on this week’s episode of the Conquer Local Podcast.

Transformation in Technology and all Industries Focuses on Efficiency and Operational Impact. 

Jeff Tomlin: Jen Swanson. Hey, welcome to the Conquer Local Podcast, and thank you for taking time out of your busy day to join us here.

Jen Swanson: Of course. Thank you so much for having me. I really appreciate it.

Jeff Tomlin: Well, pleasure to have you on and what great timing, chatting with a number of our hosts lately, or rather our guests lately at the top of everybody’s mind is this idea of transformation. And particularly in the technology space, a lot of companies are going through a transformation right now balancing this idea of growth and profitability, where in the past few years it was grow at all costs and now it’s not so easy to come by capital. So efficiency is super, super important. So it’s a big theme in the tech space, but it’s not just the tech space, it’s focusing on transformation that it’s like almost all industry categories. So first off, let’s start right at the top. When you talk about transformation, there’s a couple of different components as you define it. So walk us through when you’re talking about transformation, what are the big components of it and how do you define each of those pieces?

Jen Swanson: Sure. Well, I mean I think in the last decade or so, the transformation word has gotten a little bit… It’s lost all meaning. The word has lost all meaning to many of us, right? Because everybody uses it in slightly a different manner. I think the technology part of it has become almost like the least meaningful part of transformation, right? So we walk around all the time talking about digital transformation, and the digital part of it almost becomes the least interesting part of it because we all know… The digital transformation for me, when somebody says, “Well, what really is digital transformation?” I talk about digital transformation is taking technology and making sure we are leveraging technology to the fullest in every part of our business. So it’s not just in the old days, do we have a website? Are we e-commerce? Are we marketing online? Sure, that stuff’s all table stakes now, right?

Nobody goes around saying, “Hey, we’re going to have a web launch party,” right? Because everybody assumes you’re 24/7, 365 online, and nobody gets excited about that. The technology is ubiquitous. The parts that I think people don’t talk about, and frankly where I’m finding the most meaningful work in consulting with companies is in the operational impact of transformation and the leadership, sort of the human side of transformation. What’s the impact of the people, the organization, when you are trying to keep up with the pace of the technology change in our world, right? So a lot of times what will happen is I’ll talk to companies that it doesn’t matter what industry you’re in, everybody’s competing on experience. And when you’re competing on experience, it matters as much about how you’re delivering your service or your physical goods as it does how you’re delivering the billing and the payment ability or the servicing ability or anything that sort of surrounds the product itself. And that’s the part that I think honestly has been the most overlooked as companies have transformed from a technological standpoint, is forgetting what the impact is to operations and customer service and service delivery. And I think that’s really where frankly, most companies are catching up now and why we’re still talking about this, right? Because everybody’s sort of taken on digital transformation, not everybody has taken on that operational part of things or that operating model or that operational aspect of things.

Transformation Projects require addressing Multiple Aspects, Co-Creation Reduces Costs. 

Jeff Tomlin: Let me ask you a question. So a lot of the companies that you’re working with, is it typically a small component that ends up needing to be adjusted or transformed, whether it’s software or whether it’s an operational practice? Or do you find that a lot of the companies that you’re working with really need to change a number of different aspects of the way that they’re not just operating, but the way that they actually deliver things?

Jen Swanson: Well, so Jeff, there’s two answers to that question. Usually they come to me thinking it’s one thing, but I help them discover pretty quickly that it’s kind of everything. It’s really hard to just isolate and say, “Well, if we can just fix that one team or we can just fix that one process, it’ll be fine.” I find that generally when we are talking about transformation, it’s kind of like pulling a thread on a sweater. You pick at that one little thread and all of a sudden the whole thing comes unraveled, right? It’s very hard. And the reality is because most companies aren’t built in small, neat little isolated packages where you can just take sales over here and they’re just working over here in this nice little silo and they’re meeting kind of walled off, and then you’ve got your operations team and they’re kind of walled off and you’ve got marketing over here and maybe you’ve got IT over there. That’s not how companies function right now. And even if they are walled off like that, that’s probably not working for them either, right? So the fact is that once you start pulling on any one of those parts, you sort of start unraveling the whole sweater and you can start to see where there’s more systemic issues, there’s broader cultural issues, perhaps there’s broader leadership issues. There might be some structural issues that teams are not cross-functional, teams don’t know how to work together. One of the symptoms I often see is this idea that businesses over here working on stuff and they throw stuff over the wall at IT so that IT can fix things, right? And as soon as I hear that anybody’s throwing anything over a wall, there’s a problem because there should not be any walls in a modern organization, right? There should be teams working together towards a common goal. And so that’s where you start to nitpick at some of this stuff and you start to realize there’s broader issues than maybe a single symptom.

Jeff Tomlin: I’ll tell you what I’m hearing, giving the perspective that I have and things that we tried to change in the past in our company. Fine, when we start trying to change something, the projects always seem to get bigger and bigger, sort of the way that you’re describing. You pull a thread and then at some point, the project gets so big that it’s like, well, we can’t afford to do that. And so my question to you is, as you start to pull the thread on the sweater and unravel it, how do you approach working through transformation in sort of… Do you break it up into bite sized pieces and how do you approach getting it done? Because I imagine it could be overwhelming to an organization as you cover more and more things that need to be changed.

Jen Swanson: Yeah. So I mean, I think there’s a couple of answers to that. One is that we look for repeatable patterns whenever we can, right? So the idea is that we try to suss out some things that we might be able to try in… I mean, you can call what you want. I don’t really love the word pilot, because there’s some baggage with those kind of concepts, but the idea of some front-runner teams that we can kind of experiment on, right? And once those teams get good at it, maybe those teams help evangelize to more teams, kind of becomes a good virus that can start to spread some of these behaviours and try different things, right? So sometimes what we do is we say we’re just going to try it in a small scale experimentation and see what we can learn from it and then see if we can replicate it, right? And spread it around in a positive viral sense, right? So sometimes that’s a way for us to limit our costs. I will tell you though, that the best way I have found to limit that cost exposure for clients is to have it be something that we co-create together. So what I bring to the table is a couple of experts who have been there, done that, got the T-shirt, right? Like we’ve been to that goat rodeo before. We know exactly how it’s going to be run. We know exactly where the clowns are going to pop out, right? And all of that kind of stuff. But internally, they staff it with their people. So the man power isn’t all coming from outside the house, right? The man and women power is not all coming from outside the house and that we’re creating it together. And that has a couple of really powerful effects. One is that… I mean, clearly it keeps the cost down, right? And we become a little bit of train the trainers on some things, right? Where we can come in with our expertise, we can teach some key concepts. We’ve got sort of a lot of the tools and artifacts, and again, that expertise, we can come in and teach a small group of people sort of what good looks like. And frankly, most organizations have a couple of people in engineering, in R&D, in a nascent product organization, in UX Design who have worked in organizations that have run a product led organization before or have done product management or have done some of these different disciplines before. And we’ll say, “Put them on our core team for a while, right? Lighten their duties in their day job and give them to us and they’ll become a part of the consulting team,” right? So they’re not seeing it on their bottom line. It’s not an expense, right? But we become the team then that is working together and we manage them to deploy it. And not only is that more cost-effective, but it like the hockey stick on adoption and feeling like it’s coming from inside their culture versus it being something that some wackadoodle consultant from outside that doesn’t know anything about their culture is trying to do to them is very low because they feel like it’s coming from their peers, from somebody who knows them. And so adoption goes way up and cost comes way down, and we are co-creating it together. And so that has really helped us, that pattern has really helped us to be way more successful in companies and do it at a lower price point.

Organizations can Gain Efficiency through Transformation but not Total Net Efficiency Gain. 

Jeff Tomlin: Yeah, that makes a lot of sense. I think about the agile sort of software method of building things, and if you get a big project, it might take you three years to build a car and your client needs some transportation, but in a week you could build them a skateboard and then maybe in a month you can build them a bike and you can work your way there and do it piece by piece.

Jen Swanson: Yeah. And taking that metaphor even further, they may think they want a car, but what they really need is a motorcycle because they don’t actually need a car or they need something different. They need an airplane, right? And so part of what you need to do is kind of experiment a little bit and to do that with people who have some… Like they say, skin in the game, people who have their vested interest because they’re a part of the company and they’re not just from outside. Because no matter how much you say… And frankly we mean it, we care a great deal about whether or not our advice is taken seriously by our clients. It matters to us personally, but there’s a lot of consultants out there that have ruined that line for us. So they have to see it to believe it, and they’re much more likely to believe it when it comes from their peers inside the company.

Jeff Tomlin: Right. Is it possible for organizations… I think I know the answer to the question, but I’ll throw it. Is it possible for an organization to work through a pretty large transformation or maybe the right question is, is it typical to see that they can bring costs down, operational costs down and gain efficiency? Or do you see that maybe some of the fixed costs typically go up, but the efficiency of their organization improves and does it take time to get one or the other?

Jen Swanson: So I’m going to be super honest with you, Jeff. I have never seen a total net like efficiency gain, right? Now, what I have seen is that there are some areas where you get a huge gain, but they are often offset by expense increases elsewhere in the organization. Now, what I will tell you is that the efficiency gain may be in areas of lower value, right? Where, for example, in one of my clients, we were working with an operations’ organization that was working on digitization and they were spending a ton of money on call centre staffing that was literally picking up the phone and telling people how to find a link to print out a claims form online. Like, “Do you have a computer? Can you go to this URL? Okay, click on the blue button and then do you have a printer? Okay, print that claims form, fill it out and mail it in.” And they were doing that 300 times a day, okay? That is an exceptionally expensive way to allow a customer to self-serve, right?

Jeff Tomlin: Right.

Jen Swanson: So think about that, 300 times a day, times 30 call center agents, right? Think about how expensive that was. Now that was offset. I’m not going to tell you that we eliminated 30 call centre agents because we didn’t. And a lot of executives at that client got real excited about the idea that they were going to see these year over year expenses were like 30 call centre agents. We were going to be able to cut that head count. It was going to be so exciting. No, but do you know what those 30 call centre agents were doing less than six months later? They were spending time with clients telling them, helping them navigate really complex healthcare, like choices and how to find people. So they were taking… They had much longer call times, which if you’ve ever talked to anybody in a call centre, what do you want? Short call times so you can help more people. All of a sudden they were having these long conversations that were very valuable to customers. So all the metrics went in the wrong direction for what was typical, but all of the value metrics were through the roof because customers were way more satisfied. They didn’t have to wait as long. They got white glove treatment from these customers because we freed up these call center agents to do the high value work. Instead of saying, “Click the blue button, hit print, fill out the claim,” right? So we didn’t have to hire more agents to do the higher value work, we shifted. And I think instead of what are you going to cut versus what are you going to gain, I think you have to start thinking about the… Most companies have to think about a shift in value on both the expense and the revenue side, right? It becomes a shift towards value when you transform. And that’s I think, what’s really powerful.

Improving Customer and Employee Experience is Crucial for Organizations. 

Jeff Tomlin: And so in that process, you’ve just greatly improved the customer experience, which is what we should all be focusing on at the end of the day.

Jen Swanson: Always. Yes.

Jeff Tomlin: The only thing that matters is the experience that the customer has. And so that goes up through the roof. I feel like you’ve answered my question because I was going to ask you why is it important to focus on how work gets done in an organization? And that’s clearly one of the answers anyways.

Jen Swanson: Right. Right. And so I think that’s the other part though, Jeff, that you’re asking about is that I think it’s really easy for a lot of companies to spend all their time thinking about the customer experience and no time thinking about the client experience… Sorry, the employee experience either, right? So that same client that I had in all the years that they had spent millions of dollars on the customer experience, super fancy website, all these bells and whistles that they could do really cool stuff on the website. Nobody had ever looked at what that was doing to the call center agents. And we sat down with call centre agents and looked at it and they had to serve one customer sometimes had 30 tabs open on their desktop to serve a client because nobody had ever thought, when we introduce a new functionality to the customer, maybe we ought to integrate it on the call centre agent’s side of things. Instead, they would just make the call centre agent open a new tab. How satisfied do you think those call center agents were? And how crabby do you think they were every time they had to take a call, right? And so if we could spend a 10th of what we did on adding some new bells and whistles to a customer side of things to fix the agent side of things, we actually could put customer satisfaction through the roof. So if you don’t pay attention to that whole value chain, you start to miss some of these really obvious low-hanging fruit on how you can impact the customer experience.

Importance of Comfortable Working Conditions and Effective Operating Models in Businesses. 

Jeff Tomlin: Well, there’s that little bit of wisdom that everyone should pay attention to is that your customers will never be happier than your employees, and there’s something to that. So you got to make the working conditions really, really comfortable so that the team that’s serving your customers, they’re having a great time too, and they can deliver that service there in the mindset.

Jen Swanson: That’s exactly right.

Jeff Tomlin: Talk to me a little bit about the operating model. You guys focus on the operational model in your consultancy, and why is that important and what’s the work to be done around that?

Jen Swanson: Sure. So just to make sure that everybody knows what I mean when I say operating model, it really is a… Like that’s the nexus point of when we think about a company’s strategy, right? Where to play and how to win, the business model, how do they make money? Literally, what’s the interchange in the marketplace, right? Their people and their technology all coming together. And the operating model really is thinking about how is work organized and how does work get done inside of an organization? I’ll be super transparent, I have a bias towards product management versus project management. I am all in on product management with the… Tightly coupled to agile software development, right? So I don’t believe in agile without product, and I don’t believe in product without agile. I think that they go together like peanut butter and jelly or peanut butter and chocolate or however you like your peanut butter. And those two things together are my bias as a operating model. And that idea of organizing teams around products and products can be things that are sold, but they also can be experiences or capabilities or platforms that have to be managed over time. Just like the things that you sell, right? You may sell streaming services, right? Like a Netflix or an Amazon, but you also have to be thinking about authentication and you have to be thinking about billing and you have to be thinking about security and safety and all of those different things all have to be managed because those are all parts of the experience, just like the way that the movie is delivered to my eyeballs, right? And so all of those pieces together have to be managed and how those things are managed, that’s really the operating model. So it comes down to teams and roles. It comes down to how all of that work comes together and is governed, how success is measured, how teams are funded. All of those pieces together are the operating model. And I think why that matters is that for many years we’ve been bringing in technology that… I don’t know. You’re a youthful guy, maybe you don’t remember this, but there was a day where you used to be able to go and buy software. It came in a box. Remember we used to talk about software out of the box, right? Yeah. Raise your hand.

Jeff Tomlin: Not that young.

Jen Swanson: And you would put that disk into your tower and you’d be like, “Great, I got my software,” right? That’s not how software works anymore. The minute you buy software, it’s already obsolete. There’s 1. 1. 1. 1. 1, right? That’s going to be released tomorrow and tomorrow and tomorrow. And if you’re integrating that software with anything, it requires somebody to give it… I always think of it as care and feeding, right? Somebody who’s going to tend that software over time and make sure it doesn’t break anything else, that it evolves, that it continues to fill the needs of the company and of the customer. And so you have to structure a team around that. You can’t just plunk it on an old manufacturing model of a company that makes things in an assembly… Make software in an assembly line. You have to think about how you structure a team differently. And that’s really when we’re talking about operating model, we’re thinking about what’s the care and feeding of some of those elements over time. What’s the people, what’s the process? What’s the funding? All of that kind of stuff.

Being Product-led means Prioritizing Customer Experience and making Decisions Accordingly. 

Jeff Tomlin: I imagine so thinking product first as opposed to project, it seems like that’s a mindset and-

Jen Swanson: 100%.

Jeff Tomlin: And I would imagine that having that type of mindset probably gets you focused more on the experiences at the end of the day, whether that’s the experiences that your team has doing their work or that your customers at the end of the day experience using those systems too.

Jen Swanson: Yeah, I mean, I think that this idea of becoming a product-led organization is a concept that I think has been misunderstood, in the last couple of years, this idea of product-led growth, that’s a very specific term that applies to I think very few companies. When you think about companies that are truly growing through the product with freemium different pricing tiers and things like that, that’s a very specific part of the market that does not apply to a vast, vast majority of companies. But being product-led outside of that idea of product-led growth, really all that means is that you are putting the experience at the centre of everything you do as a company and that you are making decisions and valuing the experience of the customer, however you define the customer above all else. That’s not a bad way to do business, right? You are choosing to say, “We believe that the experience is our competitive advantage and we’re going to make choices accordingly.”

Jeff Tomlin: What a great way to think about things. And then your decision criteria when you’re picking systems that you’re going to use, whether it’s a customer-facing system or an internal system, is what’s going to give us the best experience or what’s going to give our clients the best experience at the end of the day.

Jen Swanson: And how you’re going to integrate it. Is it going to improve the experience? Is that integration going to further the experience or is it going to get us further away from the experience that we want to deliver, right?

Transformation Never Ends; Start Now and Seek Help. 

Jeff Tomlin: Yeah.

Jen Swanson: I mean, it helps you make a whole world of decisions.

Jeff Tomlin: Yeah. We could talk about this for a long time. Boy, we’ve gone through a lot of transformation just here at Vendasta, all the different systems that we’ve used, just integrating a bunch of new systems right now, and it seems like it’s never ending. As you grow and go through different phases, this constant change in the systems you use, it never ends, but you have to adapt as you grow it in different sizes.

Jen Swanson: That is probably the adage that maybe we could end on. I’m sorry to interrupt, but the thing that I always have to say to people is that if you’re asking when transformation ends, you’re asking the wrong question. Because transformation never ends. It’s ongoing.

Jeff Tomlin: Yeah. And we say around here, or at least inside of our walls, you really ship your structure. It’s not just your org structure, but the way that you organize how work is done. That’s what you ship at the end of the day and in terms of the experiences, so it’s important. If you wanted to leave the audience with a couple of takeaways, what would they be, Jen?

Jen Swanson: Oh, boy. Well, I think first of all is it’s not too late to start. I think there are leaders out there that are like, “Oh, we’re so set in our ways. We’ve been around for 150 years. We can never change. We’re old and more stodgy.” It’s just not true, period. I can guarantee it. It’s never too late. And you can always start somewhere. There’s always some place in the organization that you can start. We were talking about those front-runners. There’s probably people in your organization right now that wish that they could try something new, try to work in a new way, try to experiment with some different approaches to things. They have an idea and they don’t know where to go with it. Like I can guarantee you someone in your organization is thinking that way. So if you can figure out how to tap into that, you can start to find that little thread that you can start to pull on. So I think you’re never too stuck in your ways, and there’s always somewhere to start. And then I also think I’d be remiss if I didn’t say, and you don’t have to go it alone, right? There’s lots of people out there that have been… They’ve been to the rodeo, they know how to do this, and then you’ve got help, whether it’s peers at other companies that have gone through it, consultants that can help you. There’s a wealth of knowledge out there to help you with going through it. So that’s what I would say.

Jeff Tomlin: Change is difficult when you’re sitting there thinking about it, but it’s not so difficult once you go do it. My wife made me finally get rid of my Campfire Club Monaco sweatshirt that had 45 holes in it and tattered arms and sleeves, but she finally threw it in the garbage and bought me a new sweatshirt. And you know what? It was all right. So you just got to jump in and find a place to start.

Jen Swanson: That’s right.

Connect with Jen Swanson and Continue the Conversation.  

Jeff Tomlin: That’s right. Hey, it’s an absolute pleasure chatting with you on the Conquer Local Podcast.

Jen Swanson: Thank you so much.

Jeff Tomlin: Thanks so much for joining us, Jen, and if people wanted to continue the conversation with you and reach out, how do they connect with you?

Jen Swanson: Well, LinkedIn really is the best place to go. Tuckpoint Advisory Group is on LinkedIn. That’s probably the easiest way to go. I’m also at J.G Swanson on LinkedIn. I think we’re going to link to that in the show notes. And the other thing I will say is that I believe we’re going to have a link, I’ve got a white paper on transforming legacy organizations. So how we were talking about maybe some of the older organizations, they think they’re too big or too old to transform. We just did a case study on one. So we’ve got a link to that, I think, in the show notes that people can use. And there’s a contact form there as well.

Jeff Tomlin: We’ll make that available to everyone. Jen Swanson, it’s been an absolute pleasure. Take care of yourself, and I hope to see you back on the Conquer Local Podcast down in the future so we can pick up the conversation.

Jen Swanson: I would love it. Love it. Thank you so much, Jeff. I really had a good time.


Jeff Tomlin: Hey, what a fantastic chat with Jen! The first nugget I took away was around the initiation of transformation. It’s crucial to understand that transformation goes beyond technology. It involves operational impact and leadership. Start the change process by identifying repeatable patterns, experimenting, and fostering a culture of co-creation.

The essence of continuous transformation is another takeaway. Jen said that the journey never ends, it’s an ongoing process. Leaders can jump in at any point, encouraging innovation and seeking the necessary support to navigate the ever-evolving landscape. Embrace the idea that the pursuit of improvement is a journey without a final destination.

If you’ve enjoyed Jen Swanson’s episode discussing Digital Transformation, keep the conversation going and revisit some of our older episodes from the archives: Check out Episode 623: The PepsiCo Way: Lifelong Learning and Leadership with Jorge Alzate or Episode 622: The Art of Traditional and Digital Marketing Strategies with Darren Anderson 

Until next time, I’m Jeff Tomlin. Get out there and be awesome!