Leader Spotlight: Designing for trust and impact within constraints, with Sam Choi
Sam Choi is VP of Product Experience and Digital Design at Centene Corporation. He began his career as an Assistant Professor of British Romanticism, Internet Culture, Educational Technologies at Ohio State University. He later worked as an Internet Product Manager at MRINetwork before transitioning to eSociety, where he led the vision and strategy for its startup IT department. From there, Sam spent 15 years in product and UX at Kaiser Permanente, a national not-for-profit, integrated health plan. Before his current role at Centene Corporation, Sam served as VP of Digital Design at CVS Health, where he led teams working on consumer-facing digital experiences, including CVS.com, MinuteClinic, Pharmacy, Caremark, and Aetna.
In our conversation, Sam talks about what it really means to design for trust and impact in a highly regulated industry like healthcare. He talks about how constraints can sharpen — rather than limit — imagination and why friction alone doesn’t necessarily equate to a negative user experience. Sam also shares signals he looks for that can indicate when an organization is truly ready for digital transformation.
Regulation and designing within constraints
How did your early career in academia change the way you frame problems, ask questions, and evaluate success in digital experiences?
It was quite an adjustment. In academia, you typically walk into a meeting prepared for an intellectual battle, so to speak. In business, that’s often not the case. There’s much more collaboration. Often, the right solution emerges through the discussion itself. That’s very different from walking into a meeting with the solution already formed in your mind.
I had to adjust the way I frame problems. In academia, I might come into a meeting and say, “I’ve thought this through, and here’s what I think we should do.” In a business setting, that approach can be counterproductive — and even overwhelming — for people who want to actively participate in the discussion.
You’ve said that the most enduring creations come from working within constraints instead of escaping them. In large, highly regulated organizations, such as healthcare, is there room for imagination in design or is it about working within constraints?
Some of the designers we hire come from a tech or startup background. They’re very imaginative, and they have wonderful portfolios — we’re excited to bring them on board. But they can sometimes get frustrated with the slower pace of work in healthcare, especially given the number of reviews we have to undergo. Securing reviews from multiple stakeholders can feel like a constraint to some. But often, stakeholders like doctors bring insights into the patient experience that we, as designers, simply don’t have. Their “constraints” can often improve the experience, as they understand what patients would find uncomfortable or unhelpful.
We’ve had to adjust how we evaluate what great design talent looks like in a highly regulated environment. There’s simply less visual freedom in healthcare than in non-regulated industries. We have to comply with a wide range of laws and regulations while still designing for user trust, and not everyone has the patience for that kind of work. Something that’s highly imaginative in healthcare may not look as visually striking or creative when compared to consumer products in the tech industry.
So, how do you decide where it’s appropriate to lean into imagination? What does that look like in practice?
A lot of healthcare design work is rooted in discipline and standardization, especially in a larger company. We recognize that we’re working as a corporate author. We don’t want a design or piece of content made by one person to stand out from something another person created. We’re working for the same organization, and we need to speak from a consistent company voice.
Another way of thinking about it is: how do we come together to create a shared, collective imagination of who we are as a company? That means going deep on brand presence and personality and truly making it your own. There’s still imagination at the individual level — it’s about getting comfortable with the persona you’re stepping into as a designer and then delivering consistently on that corporate brand message and brand persona.
Readiness for digital transformation
A company may think it wants a digital or product experience transformation, without fully understanding what that entails. How do you determine if a company is actually ready for that step?
To truly deliver on digital transformation, you have to be prepared on multiple levels. In one of our transformation journeys, we realized that our platforms, systems, and processes were less mature than we thought. And while the transformation is, by definition, changing those things, you still need to reach a certain level of readiness first. You can’t do everything all at once.
We had to migrate to a more stable state first before we could move toward what we ultimately wanted to build. We spent the first two years focused on that work so we could eventually take the leap. You can’t go straight from complete chaos to an ideal future state — there’s always an interim phase. That’s a critical factor in determining whether an organization is truly ready for a digital transformation. You can’t do that work while you’re constantly putting out fires. In practice, that means you can’t pause the basic business while the transformation is underway.
What signals do you look for to tell if a company is in that stabilization phase?
The biggest factor is honesty. To take that next leap, an org has to accept where it’s at and have a sober understanding of its own maturity. Some companies overestimate their capabilities and aren’t willing to fully reckon with the technical debt they’ve accumulated. If you don’t go in with a very honest assessment of where things stand, as well as what limitations may exist, you won’t be prepared.
When constraints improve the experience
Do you have an example you could share of a time when a deep technical constraint directly improved the digital experience?
When I was at Kaiser Permanente, we were always trying to be faster and more efficient, but we often felt constrained. One area where we couldn’t move as quickly as other companies was identity management and entitlement — verifying who the customer is when we interact with them. Many people point to the financial services industry as the gold standard for identity management, but we felt that the bar was actually higher in healthcare. Trust plays an enormous role in the work that we do.
In financial services, if we get your identity wrong and you lose some money, we can give you that money back. If we get your identity wrong in healthcare, we might give you the wrong advice, the wrong medicine, or reveal sensitive information. That can instantly shatter a user’s trust. We can’t give you your privacy — or your health — back.
At Kaiser Permanente, we were working on optimizing account validation. At first, we thought the goal was to move as fast as possible, but we later realized that speed alone was not actually what users wanted. Rather, they wanted validation that felt fast — but within cultural expectations. For example, if you ask your bank for a dollar and they give it to you immediately, that feels right. But if you transfer $1 million and it happens instantly, you’d be worried. In that situation, you expect friction and additional validation.
Our account creation process felt a bit more clunky and awkward than we wanted, and we spent a lot of time trying to figure out how to make it simpler. To create an account that would provide access to medical data, we had to first definitively verify the user’s identity. So, we asked multiple questions that went far beyond collecting a name and email. We even offered the option to request verification via mailed postcard with password — even in this digital age. The process was complicated, but the users we surveyed appreciated these precautions. We realized that the friction that slowed down the validation process actually helped users feel secure and confident that they were taking the right steps. So, what we originally thought was “too slow” ended up being a good thing.
How do you measure the success of digital experience projects? Are there certain metrics that you look at?
Ideally, in healthcare, we’d measure success with our members’ health outcomes. The real challenge, though, is attribution. How can we connect a digital action someone takes today to their health outcomes, especially when the impact may not be visible for 10–15 years?
At Kaiser Permanente, we created personal action plans — things like reminders for mammograms or colonoscopies based on clinical guidelines, statistics, and a member’s demographics. These screens won’t prevent cancer, but they can detect it early and improve survivability. But how do you attribute that impact years down the line? You end up relying on interim measures like adherence, uptake, and engagement. You extrapolate impact from those signals, but it’s hard to predict how today’s actions will affect someone’s health 20 years from now.
The overlooked side of digital transformation
From your vantage point, is there something that enterprises often misunderstand about digital transformation even after investing in it for many years?
It’s less about misunderstanding and more about prioritization. Most enterprises treat the cost of digital transformation primarily as a technology investment. They focus on the expense of migrations, new flows, new UI, and similar work, but they tend to underinvest in people and processes.
A lot of support is required after the experience itself has transformed. The customer service representatives, whom people rely on when they call in with questions or errors, need to be properly trained. The processes, routing, and support models need to be updated to reflect the new experience.
Inevitably, the platform portion of the digital transformation gets funded, while the people and processes do not. Change management, communication, and retraining are all areas that typically receive less attention. I think that’s what holds organizations back from realizing the full value of digital transformations. They see the platform work as “done,” but they don’t continue investing in the people and processes required to make it successful.
How are you seeing AI impact the digital experience space?
AI is going to be transformative to product and design, and I think this year may be a turning point. In the past, AI tools felt more like toys. They could come up with impressive-looking image generations, but they couldn’t adopt the brand standards and design systems required by large Fortune 100 companies. Today, these tools are much more mature. They can ingest a design system, understand brand standards, and even generate outputs that are consistent with what brands had delivered before.
When it comes to appropriate use, leaders need to know where AI replaces work and where it augments it. There’s a lot of conversation about replacement, and that’s where a lot of fear comes from — especially from individual contributors who worry about their roles being automated. Right now, we’re seeing the most value in augmentation — making people more effective and freeing them up for strategic and more interesting work.
At Centene now, we have several efforts underway where we’re using AI technologies not to replace people, but to augment their skills and to make their jobs easier. So far, the results have been quite effective.
So, given the heightened presence of AI, what skills do you feel have become more important for digital experience folks who are earlier in their careers?
Early-career workers, especially in design, are mostly hired for their hard skill sets. They spend their days heads-down in tools like Sketch or Figma, and they can increasingly leverage AI to make themselves more efficient at that work. Later in their careers, designers who are true partners in the business need to understand how the business actually works and think critically about what’s really needed.
A product manager who owned search once came to me and said, “Sam, can you help me think about how we can enhance the search experience so we can get more searches?” For her, success was measured by the number of searches performed. But from a human perspective, no one wants to search — you search because you’re confused or you haven’t found what you need. In that case, wouldn’t a better success metric be a reduction in the number of searches?
That shift in thinking is what comes with time and maturity. Later-career leaders need to focus less on optimizing features and more on essential human and business needs. That’s the difference between execution and leadership.
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