Jessica Bogart Kasper, Head of Operations, Proximity Health

We interviewed ID alum Jessica Bogart Kasper (MDM 2020), Head of Operations at Proximity Health, via email and video call. Jessica discussed her evolution from visual design to service design, her work building operational infrastructure at a health-tech startup, and her advice for emerging designers navigating AI and career ambiguity.

Previously, Jessica served as Director of Organizational Systems Design at Kalderos, Design Strategy and Organizational Communications Lead for Global Media Operations at NBCUniversal, and co-founded PB&J Publishing, a startup reimagining how children experience storybooks on touch devices, where she served as Founder and Creative Director.

What are you doing professionally today?

I lead operations at Proximity Health, a health-tech startup focused on automating and simplifying how hospitals manage access to discounted medications through the 340B drug pricing program. As one of the company’s first employees, I’ve had the opportunity to design the internal systems, processes, and infrastructure that support everything from investor operations and business strategy to finance, HR, and day-to-day enablement.

My work is deeply influenced by my training in systems and service design—making complex, often invisible workflows visible and actionable. At this early stage, I’m building lightweight, flexible processes that meet the needs of our team today, while intentionally designing them to evolve as we grow. I see operations as an ever-adapting ecosystem: the goal is not just efficiency, but resilience and clarity, so the company can scale.

What’s your background, and how did you decide to come to ID?

I’ve shaped my career by following my curiosities and building on each opportunity as it came. I started in visual design, drawn to how communication can clarify complexity and drive impact. Over time, I realized I wanted to move beyond artifacts and messaging to shaping more holistic experiences and systems. That shift started with a children’s book app startup I co-founded—an early experiment in blending storytelling, technology, and user experience.

Around that time, I started at NBCUniversal. There, I defined my own role focused on helping leaders communicate strategy across large, complex teams. It was rewarding work with an exceptional team, but I reached a point where I felt my instincts outpaced my toolkit. I wanted to take on more complex business challenges, lead through ambiguity, and grow as a designer and operator. That’s what ultimately led me to ID—where I could expand my skills, deepen my thinking, build my network, and prepare to take on whatever challenge came next.

What was your path from ID to where you are now? And what has surprised you on this path?

Coming out of ID, I was drawn to systems and service design—particularly designing for the humans within those systems. I wasn’t entirely sure where that would take me, but I knew I wanted to help organizations work better from the inside out. Through recruitID, I connected with Kalderos, a healthcare data startup led in part by an ID alum. They hired me to help shape organization and culture design, which became a crash course in how startups function as living systems.

What surprised me is that this path led me to operations. I hadn’t set out to become an operator, but in hindsight, it makes perfect sense. My pragmatic mindset, empathy for users and employees, ability to collaborate across functions, and systems thinking all pointed in this direction. When I joined Proximity in early 2024 to lead operations, it felt like the perfect synthesis of everything I’d built: a chance to design a company from the ground up, creating the systems and processes that make growth possible.

ID helped me get here—not just by giving me the tools to think in systems, but also by creating the relationships that opened doors. The degree gave me the skills, the confidence, and the network to land in what has turned out to be my dream role.

How would you describe systems design today? Both at your organization and in the larger world?

Systems design is about intentionally shaping the interconnected parts of a whole—tools, people, processes, and data—to work together toward a shared goal. At Proximity, we think of the company as a web of systems that need to support both automation and human interaction. With a lean team, we rely heavily on well-designed systems to do the heavy lifting—whether that’s managing data flows or streamlining internal collaboration.

Because we’re early-stage, I have the rare opportunity to design from a blank slate. That means building for today’s needs while staying flexible and future-ready. Every decision is a balancing act between structure and adaptability—between what works now and what will scale.

More broadly, as organizations become more reliant on AI and automation, systems design is only becoming more critical. It’s no longer just about efficiency—it’s about ensuring that tools, people, and processes can speak the same language. Done well, systems design enables clarity, responsiveness, and resilience in a world that’s moving faster than ever.

What is exciting you now in design, and what do you foresee happening next?

At Proximity, design is deeply embedded in how we operate. Our CEO started his career as a product designer, our Head of Product is an ID alum, and our culture reflects that foundation. We ask better questions, challenge assumptions, test ideas quickly, and deeply value user research. Design helps us move fast, stay grounded in real needs, and build with clarity—even amid extreme amounts of ambiguity.

Looking ahead, I see a growing need for designers who can think in systems, navigate complexity, and lead in spaces where there isn’t a clear playbook. Personally, I’m already in that space—most of what I do day-to-day, I’ve never done before. I’ve never managed finance operations or built and implemented a CRM. I’m learning constantly, stretching both my design skills and my leadership capacity. I’m excited for the next stages of Proximity, where I’ll have the chance to evolve our culture and support our team’s wellbeing and success. These are some of the most complex and rewarding design challenges I’ve ever taken on.

The more design thinkers we bring into the core of organizations—not just to shape products, but to shape how we work and grow—the better equipped we’ll be to meet the challenges ahead.

What would you tell emerging designers about how to position themselves for tomorrow?

Here are a few principles that have shaped my own path:

Never stop learning.
The world is constantly changing—tools, systems, technologies, expectations. Part of the designer’s edge is how we see and approach problems differently. Keep your toolkit sharp, stay curious, and explore new methods, even if you’re not sure when you’ll use them.

Define your superpower.
It can take time, but everyone has one. Figure out what energizes you and where you bring unique value—whether it’s storytelling, systems thinking, facilitation, or something else entirely. Then nurture it. Just know that it might evolve, and you should evolve with it.

Think of your career as a snowball, not a ladder.
This is something I first heard at ID, and it really stuck with me. You’re not just climbing up—you’re collecting experiences, skills, and relationships that will shape your direction in unexpected ways. Be open to pivots. Some of the most meaningful roles don’t look linear on paper.

Be patient and intentional.
Early in your career, it’s easy to want to sprint. But it takes time to build the foundation you’ll stand on later. Plant seeds—skills, relationships, ways of thinking—and give them time to grow. Eventually, those investments will compound in surprising and meaningful ways.

Learn to lead through ambiguity.
Many of the most rewarding roles—especially in startups or unstructured environments—won’t come with a playbook. That’s where design training becomes invaluable. Trust your process. Start with questions. Map the system. Prototype your way forward.

Relationships are just as important as skills.
So much of career growth is about timing and connection. Stay curious about the people around you. Listen well, contribute generously, and nurture the relationships that energize you. Many of the best opportunities won’t come from applications—they’ll come from conversations. And if you’re anything like me, and your superpower doesn’t fit neatly into a single box, those relationships can help you create a role that truly reflects who you are and what you bring to the table.

How should designers entering the job market be thinking about AI?

It’s a complex moment to be entering the job market. Organizations are experimenting with ways to reduce costs (often headcount) and streamline operations through AI and automation. For new designers, that can feel intimidating—but it’s also a signal of opportunity.

If we know companies are trying to maximize AI and automation, the question becomes how? The real challenge lies in implementation—translating strategy into systems that actually work at scale. That’s a design challenge as much as a technical one. It’s about understanding people, processes, and the ways technology can augment both.

Mastering AI takes time and curiosity—qualities that emerging designers often have more room to cultivate than busy leaders. Leaders can explore or dabble, but they may not have the hours to deeply learn, build, and integrate. So, if you can bring AI fluency—an understanding of how it works, how to use it creatively, and how to talk about it intelligently—you’re offering something many organizations don’t yet have.

As a student or early-career designer, one of your superpowers is time to learn and experiment. Dive into tools, create small projects, test integrations, and push the boundaries of what AI can do for design. The more you can show how to make AI real and valuable within an organization, the more indispensable you’ll become.

What have been some of your biggest lessons and proudest moments?

Challenges
One of the biggest challenges throughout my career has been figuring out what’s next at each transition point. My path hasn’t been a straight line—it’s more like a scatter plot of dots, each connected by introspection, opportunity, and crucially, relationships. I’m not someone who lands roles by applying to job postings. Almost every position I’ve taken was offered by someone who truly understood my potential and trusted me to lead in unfamiliar territory. This ties directly into one of my biggest principles: careers are as much about relationships as they are about skills. Every opportunity I’ve taken has involved stepping into something I’ve never done before—and succeeding because someone believed I could figure it out.

Lessons
I’ve learned to be comfortable with being uncomfortable and expect ambiguity. It’s like building the plane while flying it. But I’ve learned to trust my skills, my judgment, and my ability to ask the right questions. When a problem feels daunting, slowing down to understand it often reveals the next best steps.

Proudest moments
I’m proud of many milestones, but here are a few that stand out:

1. • Taking the leap to go to ID: This might sound a bit cheeky since this is an ID interview, but deciding to pursue my master’s was a big leap for me. I was in a comfortable role that I could have stayed in for years, but I chose to step into the unknown to learn and grow. I miss many aspects of that job, but I know this decision was the best investment in my future.
   • Demoing Proximity’s first product: For over a year, we exhibited our vision without having a real product in anyone’s hands—just strong hypotheses about the market. Finally demoing our product in February and witnessing the strong reactions from customers was incredibly validating. It represented years of work—from fundraising and prototyping to hiring engineers and designing the user experience—all coming together in a moment that proved we’re onto something big.
   • Being a mom while building a career: The transition into parenthood is challenging on its own. Adding the demands of a passionate, dedicated career creates its own complexities. I recently returned from parental leave with my second son and feel proud of the balance and juggle I’m managing so far. It’s not easy, and to all working parents out there—I see you and you got this!

What’s an image or a moment that comes to mind when you think of ID?

Graduation. I was part of the Class of 2020—we were in person for just one semester before the world shut down. But true to form, the graduating class came together to design a sendoff that was personal, joyful, and uniquely “ID.”

We didn’t want to end our experience alone in our living rooms, staring at a Zoom screen. So we collaborated with the administration to co-create something that felt meaningful. We mailed balloons and disco lights to all of the graduates to enjoy during a virtual party. We submitted videos of ourselves “walking the stage,” which were edited into a celebratory graduation montage we watched with our families. We built a Miro board with each graduate’s photo, where classmates and faculty left notes of encouragement, gratitude, and reflection.

But what really made that moment special was how it came together. It was only possible because of the deep relationships we had formed with each other—the kind of bonds that made us want to build something together, even in the midst of chaos. It was also a reflection of the relationship we had with the administration, who consistently went above and beyond to support and celebrate the students. And finally, it was a moment where we got to live our design education: co-designing across many voices and perspectives, breaking into working groups, rapidly ideating and delivering ideas, and staying focused on creating something human and heartfelt.

That’s what ID is about—creativity in the face of uncertainty, and community at the center of everything.

What do you most value about your ID experience and why?

One year wasn’t enough to “learn it all,” but it was more than enough to change my trajectory. ID opened the front door to the methods, mindsets, and community that continue to propel my career forward. The curriculum and faculty pushed me to develop new skills and frameworks, especially around how to lead in complex, collaborative environments. I learned not just how to solve problems, but how to frame them—how to navigate ambiguity with curiosity, empathy, and rigor.

And I can’t talk about ID without talking about the community. The strength of the ID network is incredible. There’s a deep generosity that connects alumni, students, and faculty—if you reach out, someone will help. That spirit of support and shared ambition continues long after graduation, and I feel lucky to be a part of it.

Where do you see design increasingly providing value or taking a larger role?

I believe design can powerfully influence any industry. As an operations leader, I see how design can shape the interconnectivity and productivity of business operations—especially as AI becomes embedded in how we work. Narrowing in on a field I’ve grown deeply familiar with: healthcare.

Healthcare is a complex, high-stakes system that touches everyone yet remains fragmented, opaque, and often dehumanizing. Tremendous effort and investment go into innovation, but without thoughtful, human-centered design, even the best ideas risk becoming noise instead of solutions.

Design is uniquely positioned to help—not just by improving patient experiences, but by making systems legible, workflows intuitive, and decisions more equitable. The value of design is shifting from how it looks to how it works: how we make sense of ambiguity, align diverse stakeholders, and create solutions that hold up in real-world complexity.

As AI becomes more central to how we work and make decisions, the need for human-centered design only grows. These tools are powerful but not inherently human. Without intention, they can reinforce bias or erode trust. Designers play a critical role in ensuring AI is ethical, transparent, and aligned with real people’s needs.

More broadly, design is evolving into a discipline of leadership. We’re shaping culture, building teams, and setting strategy. Designers who can move fluidly across levels—from system to service to detail—and who can navigate the intersections of technology, operations, and human experience will be indispensable.

Learn more about ID’s Master of Science in Strategic Design Leadership (MS-SDL), formerly the MDM program.