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Navigating the AI Landscape: Leadership Strategies for Success with Hunter Jensen
Episode 531st July 2025 • Unstoppable Success • Jaclyn Strominger
00:00:00 00:26:15

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This podcast episode features an enlightening discussion with Hunter Jensen, the esteemed founder and CEO of Barefoot Solutions, who has been at the forefront of digital innovation for over two decades. A salient point of our conversation revolves around the evolving landscape of leadership in the face of technological advancements, particularly artificial intelligence. Hunter elucidates the pressing need for organizations to deploy internal AI tools that safeguard proprietary information while simultaneously enhancing employee productivity. Furthermore, he emphasizes the dual pillars of effective leadership: strategic direction and the empowerment of team members, underscoring the significance of trust within this dynamic. Ultimately, our dialogue reveals that investing in human capital is paramount, as it not only cultivates a sense of pride but also fosters a resilient organizational culture poised for success.

The podcast presents a profound dialogue between Jaclyn Strominger and Hunter Jensen, the esteemed founder and CEO of Barefoot Solutions, a company that has been at the forefront of digital innovation since its inception in 1998. Hunter shares his extensive journey from a solitary freelance web developer to leading a company that has adapted to the evolving technological landscape, including early forays into mobile applications and more recent ventures into artificial intelligence and machine learning. He elaborates on the strategic pivoting of his business model, which was essential for maintaining relevance in a rapidly changing industry. Hunter's insights into the importance of adaptability and foresight in leadership are paramount, demonstrating how a commitment to continuous learning and innovation has been integral to the success of Barefoot Solutions.

Moreover, the conversation delves into the dynamics of managing a diverse team, where Hunter underscores the significance of effective communication among varied personality types—from creative designers to analytical engineers. He posits that fostering a culture of collaboration enhances problem-solving capabilities and ultimately improves project outcomes. This segment highlights the necessity of understanding different communication styles and the role of leadership in bridging gaps between team members, thereby facilitating a cohesive working environment. Hunter's leadership philosophy, which emphasizes trust and autonomy, serves as a guiding principle for his organization, allowing employees to thrive without the constraints of micromanagement.


In discussing the implications of artificial intelligence on leadership, Hunter presents a compelling argument about the necessity for businesses to develop tailored AI strategies that ensure the protection of proprietary information while enhancing operational efficiency. He articulates the trend of deploying private, internal AI assistants that cater to specific organizational needs, thus empowering employees to leverage technology in a safe, effective manner. This proactive approach to integrating AI within business frameworks reflects a broader understanding of the evolving landscape and the responsibilities of leaders to equip their teams with the tools they require to succeed in an increasingly digital world. Ultimately, the episode encapsulates the essence of visionary leadership—strategic foresight, empowerment of personnel, and the commitment to innovation, all of which are indispensable in navigating the complexities of contemporary business.

Takeaways:

  • Hunter Jensen, founder and CEO of Barefoot Solutions, has transformed the company through various technological reinventions over the last two decades.
  • Leadership must balance between strategic direction and employee empowerment, fostering an environment of trust and autonomy.
  • To effectively leverage AI, organizations must develop internal systems that protect proprietary information while enhancing productivity.
  • Diversity in personality types within teams can lead to improved problem-solving and innovation, as different perspectives elevate overall outcomes.

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Transcripts

Jaclyn Strominger:

Well, hello everybody and welcome to another amazing episode of the Unstoppable Leadership Spotlight podcast.

I am your host, Jaclyn Strominger, and on this podcast we hear from amazing leaders and their game changing insights on how they can be better leaders for today and tomorrow. So today I want to welcome Hunter Jensen and he is an amazing individual and I'm just going to pull up his amazing bio.

e establishing the company in:

As a freelance web developer, he has transformed into a trusted partner for renowned brands such as Microsoft, Salesforce and Samsung. So it's quite unique.

He blends a personalized touch of a boutique agency with the capabilities of a large consultancy delivering ROI driven software solutions. So, Hunter, welcome to the Unstoppable Leadership Spotlight podcast.

Hunter Jenesen:

Thanks for having me, Jaclyn.

Jaclyn Strominger:

So it's so glad to have you here.

o when you started it, but in:

So what I'd love to hear from you as the CEO, how has your journey been with coming up with that 12 and the full time and contractors?

Hunter Jenesen:

Sure, yeah. So, you know, when I started this company, it was just me, I bootstrapped it.

I was a, you know, freelance web developer when I was in college and just started doing that full time. When I, when I graduated from college and moved out here, San Diego, and we grew organically for many, many years.

I, I, when I realized that you can only, you know, make so much money when you're billing your own hours, I decided to really get serious about starting the company and, and hiring folks to do the jobs that I was bad at or that I didn't like doing. And in that way, we really grew organically over time.

You know, we started off as a web development shop and then we've reinvented ourselves probably four or five times since then to stay relevant, you know, for, for example, we got into mobile apps really, really early on. We were one of the first hundred apps in the app Store. So like very early days, I think that was.

Jaclyn Strominger:

like, I just remember like in:

Hunter Jenesen:

Like, yeah, it's funny. Cause I, I'm doing kind of the same thing that I did for mobile right now. You know, when, when it really started to catch on. Yeah.

Everybody was like, okay, so we need a mobile strategy. Does anybody know what that means?

Jaclyn Strominger:

Right.

Hunter Jenesen:

And it was a brand new concept, so, you know, people didn't really know how to approach it. And so I did a lot of speaking and kind of educating folks on different strategies and what makes sense for their business and all the rest of it.

Exact same thing's happening in AI right now. Right. We need an AI strategy. What is our AI strategy? Does anybody know what that means?

And so we do a lot of consulting work for companies in that space right now. But to get back to the journey, so we were a web shop and then we were doing mobile apps.

And then we got really into the Internet of things and building software for medical devices and smart connected devices. Then we got into crypto and blockchain for a little bit when that was hot.

And then about seven or eight years ago, we did our first machine learning project, which I would say is like our entry into AI, because this has been around a lot longer than generative AI has.

And the way that I had been running the company was hiring folks in San Diego to manage client relationships, to manage projects, to do graphic design, user interface, user experience design and that kind of thing, and then contract out the actual development of a lot of these projects. And so I did that for many years. I did it all across the globe. I've done Southeast Asia, I've done South America.

I found my sweet spot in Eastern Europe. And so I was working with several contract teams in Eastern Europe. I like their education model. They have great IT infrastructure.

The pricing is not the cheapest in the world, but it's a lot less than than in America for engineers. And so I was working with these contract teams and I came in touch with one in particular that offered to buy controlling interests of my company.

So in:

And so I have my team that used to be based in San Diego, now has kind of distributed and is all over the country. And then we ramp up and down on developers as needed as projects and clients come, come and go and projects get completed.

So that's why I can't give you a great answer in terms of how many people are working on barefoot projects today because it changes very, very regularly. So that's been, our structure works very well. It allows us to price competitively versus all Americans. Gets very, very expensive.

And so we were able to pass that on to our customers. So that's kind of why we're set up the way that we are.

And what, it's a differentiator for us in that you get the like white glove kind of high touch boutique agency feel. But if you need like 15 developers, I can have them started, you know, in a week or two.

Jaclyn Strominger:

Right.

Hunter Jenesen:

And most age, most boutique agencies can't do something like that.

Jaclyn Strominger:

Right.

Hunter Jenesen:

They're always managing a bench and maybe have a few people ready, ready to work on a new project. So that's a, it's a big differentiator for us.

Jaclyn Strominger:

That's huge. So, so from a leadership standpoint, how do you, you know, how do you manage the personalities and you know, of all of that?

Hunter Jenesen:

Yeah, well, it's, it's really interesting and I, I, I hate to generalize, but I've been doing it long enough that I can generalize a little bit in that we've got two or three types of personalities. I have my creatives who are doing UI UX design and branding and copywriting and all things like that.

And they have a certain personality, typically not all of them, but. And then I have engineers and they have a very different personality.

And then I have my project managers who are extroverted and relationship people and you know, they're the ones that engage directly with our, with our clients.

And you know, often I am or kind of top leadership is serving as a conduit between those types of personalities because they don't always speak the same language. But, but I need my UI UX designer to be able to communicate to my engineers what needs to be built.

Jaclyn Strominger:

Right.

Hunter Jenesen:

So there has to be that level of communication between these different personality types.

And you know, it's, it's actually really fun because they tend to approach problems differently and when you get, you know, a diversity of opinions and voices, it lifts everything up.

Jaclyn Strominger:

Right.

Hunter Jenesen:

Like the friction is, is good, it's a positive, you know, if, if they're not agreeing on something, the outcome is going to end up being better than if just one person made the decision and then we ran with it. Right. It elevates all of it.

And so I actually really love that we have diverse personalities in the organization and there's typically not much conflict between them. But sometimes the communication styles need to be, I need to remind them that they're talking to engineers and the engineers think in a certain way.

And that's easy for me as a retired engineer, we'll call it. I still do some architecture and stuff.

Jaclyn Strominger:

But so when you're thinking about the team, I mean obviously that communication and obviously, you know, with the different personalities, do you, as you're looking at people, how, how important is it for whether they're contract or full time employees to have a certain set of values?

Hunter Jenesen:

Yeah, it is different. It is different. At the end of the day with my contract team at my parent company, I am not their boss, I am not their CEO.

They work for my parent company and that's where they get their paycheck. And so I have to be very aware of that as I tend to act like a CEO, you know, regardless.

But I have to be very conscious of letting them do their thing to a certain extent. You know, as an example, like we'll do an all hands with just the, just the American folks once a month that the contract team doesn't come to.

We also do other meetings where the entire group comes. But you know, the contract team is, is a, it's harder to manage because they're coming in and out.

It's not always the same people, it's often new people.

And so getting them to kind of understand how we operate and how client relationships work for us and all the rest of it is kind of a constant education as people are coming in and out of our projects.

Jaclyn Strominger:

Yeah, that's actually kind of interesting.

So one of the things that you're working on and you know, you said, you know, chatbots and, and obviously custom software development, but I want to kind of talk a little bit about the chatbot and people and what you're seeing in the, in out there as you're talking to businesses. How, how is AI in your opinion, affecting leadership at companies?

Hunter Jenesen:

That's a really interesting question. So I'm actually, as I talk to these businesses, I'm actually seeing a trend right now, a very clear trend.

There are, there is a segment of businesses, a large segment of businesses that can't really use ChatGPT. And the reason that they can't is they're dealing in proprietary, confidential, confidential information all day.

And they need the large language models, they need the AI to know that information to really be effective for them.

Jaclyn Strominger:

Right.

Hunter Jenesen:

And so what we've been seeing a lot of at these types of organizations is the desire to deploy you know, I'll call them assistants because chatbots doesn't do it justice. But deploying these, like, private, internal, on premise, you know, AI assistants and agents to help do their job more effectively.

And so this has all sorts of interesting implications, right? For lawyers is a great example. You know, they want to be able to do this to help them draft contracts or applications for patents or what have you.

But maybe it's as simple as, you know, an HR assistant, right?

When Sally wants to know whether or not Invisalign is covered by her dental benefits, right now she has to email HR and HR has to go look up her records and figure all that out. And it takes a lot of time.

And there's no reason that we need humans to do that kind of stuff anymore with the new technology that's come out only in the last three years.

Jaclyn Strominger:

Right?

Hunter Jenesen:

And so what we're seeing is rather than like trying to go after particular use cases, we're seeing leadership deploy platforms, their AI platform that touches all different parts of their business.

Because, you know, employees or employers, CEOs should be worried that their employees are leaking confidential information to these large language models because they're doing it. And so you need to give them the tools so that they can level up and be more productive and more efficient using this amazing technology.

But you need to give them in a way that is safe for your business. Right? Boundaries, Exactly. In kind of a walled garden, if you will, bubbles them up. And so that's where I see leadership really driving, right?

Whereas, you know, someone that's an employee might think, I really need a tool that can help me do X. And leadership is thinking we need to empower all of our employees to use this technology. Right? Because leadership is really just two things, right?

It's strategic direction and then empowerment and then just get out of the way, right? Make sure we're all rowing in the same direction. We have a clear vision of where we're headed.

You have all the tools and people and resources and knowledge that you need to do your portion of that, and then call me if you need me, if you need anything, right? And otherwise, I trust you to get the job done.

And so I think that's kind of how those two things tie together is we need some new tools to give to our team so that they can use this incredible technology. Because right now there's a whole lot of people that are getting a little bit left behind because of the confidential nature of what they're doing.

You know, you're a wealth advisor, you're an accounting firm or you're a law firm, you know, you name it. We're seeing companies spend and deploy these type of solutions like now, like this year.

Jaclyn Strominger:

Yeah, I find it truly fascinating and something that you just said. And so listeners, I really want you to hone in on this because I think it is so truly important.

Hunter just said leadership is kind of two key things. It's your strategy, where you're going and empowerment. And part of that empowerment is trust.

And so, and so like zone in on that because it is so important for you, you know, as leaders and for all of us as leaders to know that strategy, but also to empower, like we are here to empower our people and to trust our people and to work with them to get to know them.

And then, you know, I think what's great about having AI in that realm of it is that there are ways that you can even use that to help your, to help your people become more empowered as well. It's really, I think it's fascinating.

Hunter Jenesen:

Yeah, yeah. You know, you know I mentioned at the beginning, right, that we've reinvented ourselves four or five times over the course of the last 20 plus years.

That's the strategy part, that's the CEO strategic vision. This is what we're doing now. And it's not always easy or obvious.

You know, a lot of, I love my job because a lot of what I get to do is tinker with new tech because I'm trying to figure out where the puck is going, right. And so I'm always evaluating new technologies.

I was, you know, early beta user for Chad, GPT, all, you know, all of that sort of stuff and that's all. And I read like two hours a day, I just read news about technology and tinker with things and all the rest of it. So that's the strategic part, right?

And that's a big part of, of, of every day and of longer term thinking and planning and all the rest of it. And then there's the empowerment part, right? And for the empowerment, you know, I hate a micro management, right. And that's not my style.

That's not how we operate at barefoot. And so it's, it really is a lot about trust, right. I hire the types of people that I can trust to do great work because we do great work here, right.

We have a high bar of excellence and I can trust them to be autonomous. I don't need to direct them every day. I don't need regular stand up meetings with all of them or any of that stuff, they're just great.

And if they're not, they don't last very long here. It's just not. It's just not in our culture. Like, if you need to be micromanaged, then this is not the, you know, just not the place for you.

And so a big piece of empowerment is trust. And then there's just the nuts and bolts of it. Do you have what you need? How can I help you? What would make you level up? What would make you better?

What would you like to spend time learning? Which is a big one for me. Right. Like, you know, we're.

We're embarking in this new space, and I'm extremely knowledgeable about it because I get to read for two hours a day and all the rest of it, but they don't. They're in the trenches.

So how do I educate them on what is happening in the world of technology right now and get them up to speed so that they can deliver better outcomes for our clients? So trust is really important. Education is really important. Autonomy is really important. And then just make sure they have what they need. Right.

All the tools and the time and all the rest of it. If you can get those pieces right, then they'll. That they'll love to do great work. Right. You create a place where they are proud of what they do.

One of our core values is actually just be proud of your work, because if you're proud of it, it means you worked hard, it means it's high quality, it means that you care.

Jaclyn Strominger:

Right.

Hunter Jenesen:

And so if, you know, I really try to instill that sense of pride in our work because I feel like it trickles down into all these other things that we want from our team.

Jaclyn Strominger:

Yeah. So again, huge key insight, you know, trust and, you know, you know, what to almost like to put it all together in a.

In a package is to also say, invest in your people. And they will. And if they feel that investment, it's going to come back tenfold because they're going to appreciate it.

And then if they can, because then you're taking pride of them, and they feel that they're going to also then really want to have the pride in the work that they're doing, and they kind of go hand in hand.

Hunter Jenesen:

That's right. That's right. Invest in your people. I mean, my. My chief operating officer I hired as an intern.

He was the very first person I hired 19 years ago or 20 years ago, and. And he's still with us. And it's very rare that someone quits Here, because I think they feel that investment.

They know that I care and that we as a company are working together to, to solve problems and to, you know, drive ROI for our clients. Right. Like, that's what, that's what we do here. And so when you invest and they know and they feel it, they stay.

And I mean, and that's like just a very practical thing. The cost of losing someone, especially with a smaller team, you can't even put a number on it. I mean, you can't. They're so valuable.

And the longer they stay, the more valuable and the more productive they become and the more helpful for the business and all the rest of it. And so, you know, the people is the most important thing, period, Full stop. It's the people.

Jaclyn Strominger:

Right.

Hunter Jenesen:

It's also one of the hardest things.

Jaclyn Strominger:

Right, right, right, right.

Hunter Jenesen:

It's. It's.

Jaclyn Strominger:

It is so valuable. You know, Hunter, you have such great insights, and I. And I would imagine that the.

What you do for your clients as a company is absolutely quite remarkable because you, as a human are quite remarkable, and you're a great leader, and I could tell you're a great CEO. How can our listeners connect with you, learn more about you?

Hunter Jenesen:

Absolutely. Please don't hesitate to reach out. You do not need to be a potential client to get on the phone with me. I'm very active on LinkedIn.

You can find me there or just send me a direct email, hunterfootsolutions.com I will reply. So please don't hesitate to reach out. I love talking all things business and technology, and so I'd love to. I'd love to speak to your listeners.

Jaclyn Strominger:

Awesome. Well, fantastic. So, listeners, we've had some amazing insights here on the show today.

I would love for you to do me the favor and reach out to Hunter, connect with him, and then please go one step or two steps further, actually, and hit subscribe if you haven't already. And also, please share this episode with.

With as many people and friends and colleagues as you can, because there's some really amazing insights in here to be a great leader. And again, if we can create more great leaders, we'll have greater people in our society. I'm Jaclyn St.

The host of Unstoppable Leadership Spotlight Podcast. And thank you, Hunter, for being a great guest.

Hunter Jenesen:

Thank you, Jack.

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