Leading with Empathy & Innovation: Kurt Donnell of Freestar

1. What role does leadership play in ensuring innovation initiatives remain aligned with employee values and customer empathy? 

At Freestar, it starts with a clear vision and strong core values that serve as a compass for every decision we make. Innovation only works when it supports that vision and stays true to what our employees and customers genuinely need. Without that foundation, it’s easy to drift. With it, we can evolve while staying true to who we are.

Evolution and innovation are constants in our industry, and we've worked thoughtfully to build a culture in support of this. But we never innovate just for innovation’s sake. We firmly believe that innovations must be driven by what our customers and partners truly need. That means not chasing shiny objects, not working in silos, talking to everyone, and using stakeholder feedback to shape solutions. We know that sometimes there’s a difference between what the customer actually needs and what they think they want. It’s our job to understand them well enough to decipher that difference. The goal is to create value, not novelty, particularly given our business model where we only win when our partners win.

Leadership’s job is to help carve the initial path, guide pivots, bulldoze the hurdles, and create space for top-down vision and bottom-up insight to meet. When innovation is not just new, but meaningful and values-driven, that’s where the magic happens. At Freestar, we believe we are playing the infinite rather than finite game and always do our best to focus on long-term impact, not quick wins. 

2. How does your organization balance digital transformation with maintaining a strong human-centered company culture?

Digital transformation should enhance the human experience, not replace it. Technology makes the hard things easy and the impossible possible. AI and technology allow us to exceed human potential. But what sets an organization apart is the humans behind it and the customer service.

It’s pretty simple: work smarter, not harder. We use technology for what it’s great at—data collection, speed, automation—so that our people can focus on what they do best: building relationships, solving complex problems, and delivering the high-touch, white-glove service that we pride ourselves on. The key is knowing when to rely on tech and when to lean on people. For example, automation can make a simple transactional process seamless. But when nuance or empathy is required—like with a high-stakes issue or a critical client need—a human should step in. There’s a fine line between using AI to improve outcomes and losing the human element altogether. We’re intentional about always navigating the line with an unapologetic bias for the human side of things.

Ultimately, great technology is only as powerful as the humans behind it. Our culture is rooted in empowering our team with tools that extend their capabilities, again, not replace them. We encourage the use of technology to give time back, offer clarity, and make space to focus on the human-centered work that truly moves the needle for Freestar.  We also try to leverage technology to meet our customers wherever they would like to be met, providing direct access to our teams via tools like Slack and Zendesk, which actually enhances the human connection. 

3. In your view, what elements of the customer journey must remain human-driven despite advancements in automation? 

Ultimately, I believe that sales will always be human-driven. It isn’t just about offering solutions. It’s about uncovering the right problem to solve. Often, the challenge a customer states isn't the real issue. They may articulate a certain pain point or challenge, but not the true problem. That’s where that irreplaceable human intuition comes in. A great salesperson digests more than just words or survey data. They are reading the room, picking up on tone and body language, and gathering those subtle cues to get to the root of the concern. There’s a nuance to conversations that automation, no matter how advanced, simply can’t replicate. The ability to build trust, ask the right follow-up questions, and adapt in real time is key to creating long-term value and successful partnerships. 

AI can absolutely support sales by offering insights, uncovering patterns, and saving time on remedial or repetitive tasks. But the core human interaction is still needed. It’s those person-to-person moments that uncover the underlying needs, create tailored solutions, act as holdovers when the train derails, and ultimately drive success. At Freestar, that human element isn’t a nice-to-have—it’s an essential part of our business. It’s how we solve problems and build lasting relationships.

4. How is your organization innovating to improve customer experiences without making interactions feel impersonal or overly automated? 

We focus on using innovation to enhance the customer experience rather than replace the human connection altogether. Our approach to customer service ensures there’s always a human available to jump in, but only when the customer wants or needs that support. It's about finding that balance of being present without being overbearing.

A key goal for us is reducing friction. We always want to resolve issues in the fewest number of interactions possible. That means getting the right people involved quickly, clarifying the request early on, and offering thoughtful follow-up. No customer wants to hear, “We’ll get back to you soon”—they want the answer right away.

When it comes to utilizing automation, there’s definitely a sweet spot. We always ask: is this helping the customer, or just creating another step? Helpful automation—like being able to track a ticket in Zendesk or receiving a smart notification about travel delays—adds value. But too much automation can feel impersonal and even frustrating.

We talk internally about the creepy vs. convenience scale. If it feels like tech is reading your mind, that’s only great if it’s actually helpful — nobody wants to feel followed. Our goal is to stay on the side of convenience. It circles back to that idea of finding the right balance. We want to deliver faster, smoother experiences without losing the human touch that builds trust and long-term relationships.

5. How do you evaluate whether a new innovation might unintentionally erode human trust or connection? 

Evaluating whether an innovation erodes human trust often comes down to gut instinct. To do this, we put ourselves in the customer’s shoes, asking: Will this improve their experience or be more frustrating? If our offering ends up feeling like a “call-your-cable-provider” to get answers, that’s a huge red flag. At the same time, we try to stay objective. Sometimes automation brings real value. But we always weigh that against the potential for subpar customer service. If the savings or speed improve the experience and build trust, it’s a win. But if it leaves people wishing a human were involved, we’ve missed the mark.

Internally, we focus on helping our team thrive alongside automation by showing them how AI can amplify their potential. It’s about demonstrating how tools like AI can make their work easier, better, and faster, and ultimately help them grow in their careers. We also invest in a broad ecosystem of support—learning opportunities, mentorship, book clubs, and programs that connect employees across teams and levels. This helps reinforce internally that growth isn’t just about tech, but about human connections and knowledge sharing.

While we lean into automation where it adds value, we’re intentional about keeping a human touch. We always want it to be clear to our customers and our team that effort and care remain front and center.

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