In Conversation with

Sherry Eckholm

Interview with Sherry Eckholm, Director of Strategy at Loft

Guided by her strong principles and business acumen, Sherry shapes meaningful encounters by introducing innovative business frameworks and value propositions that truly make an impression.


Gregor Mittersinker

Sep 28, 2023






Sherry Eckholm


Director of Strategy at Loft Design

Meet Sherry Eckholm, our newest team member at Loft. She joins us with 25 years of experience in corporate and consulting, spanning product design, user-centered research, design strategy, and recently a venture designer. Her experience building and scaling a design team and toolkit within a corporate startup studio has given her a unique perspective, ensuring Loft's clients invest their time and money into strategic and viable market opportunities. 

Today, we dive into her journey and glean insights into the ever-evolving landscape of innovation and design.

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. . .

Gregor Mittersinker: Sherry, throughout your career, you've navigated the worlds of corporate giants and nimble design consultancies. Do you see any differences in the toolkit and approach each uses in framing and tackling problems?

Sherry Eckholm: The tools might change, but the core approach remains pretty consistent. I firmly stand by "clarity of problem before clarity of solution." Before gearing up to build a new product, spin up a team, or write a single line of code, a crystal-clear grasp of the problem you're tackling is crucial. It's worth noting that new businesses often need help to nail that product-market fit. They deeply understand the market or industry but need a deeper understanding of their customer's core problem before rushing into the solution. Which, by the way, is pretty common! Most people jump from an idea to working on the solution.

I do think this characteristic is amplified in founders and entrepreneurs. They dare to believe that their solution to a problem will do the job better and be more meaningful to customers than what is currently out there. For the record, I use the term "dare" with reverence! Most founders' risk-reward tolerance is high, especially in the beginning, so the toolsets used to test desirability and feasibility should match this pace and risk tolerance.

In the corporate world, they have a "mothership advantage" – access to proprietary data, distribution networks, industry expertise, capital, and powerful connections. It's any of these in combination that gives them the confidence to create something entirely new or deeply valued by their customers. Of course, a corporation's appetite for taking large innovation risks is much lower, and the toolsets and approach to innovation reflect this.

Gregor Mittersinker: One advantage that many founders have is that they have "lived the problem." Famous examples are the founder of eBay, who just wanted a better way to find Pez dispensers, and the YouTube founder, who wanted to watch Janet Jackson's wardrobe malfunction video. So many unicorn startups are galvanized solutions rooted in personal discovery journeys.

Sherry Eckholm: I agree 100%. Take Brian Chesky, the Co-Founder of Airbnb. Who, by the way, is an Industrial Design graduate from RISD and the only designer who is a CEO of a Fortune 500 company! He's always said their success hinged on having a novel idea born out of his lived experience. He and his roommate needed rent money and had an apartment with a sofa as their value proposition. But it's not just about the idea; it's how they obsessively focus on the user experience on both sides of AirBnb's marketplace that matters.

Gregor Mittersinker: Founders have a certain level of grittiness and resilience, even in the face of fundraising challenges and scaling woes. How does that come into play, especially when they're shaking up old-school industries?

Sherry Eckholm: It's grittiness, determination, and OWNERSHIP. They're driven like no other. They live and breathe their solution and are in the driver's seat 24/7. Equity is a powerful motivator! And, because there isn't corporate hierarchy and politics to navigate for approval, they can move at a pace that corporations can't. That is, of course, until they have VCs and board members to answer to!

In a corporate setting, it's tough to measure the equity of an idea across its development journey, from seed idea to celebrated solution. But that doesn't mean there aren't benefits to corporate venture creation. Sometimes, a disruptive solution needs the patience and the capital to weather the volatility of markets and implement emerging technologies. I've witnessed this first-hand with portfolio companies and seen this play out as VCs become much more conservative with their investments.

Gregor Mittersinker: What tools and toolkits do you use in a corporate venture studio environment to mimic or incentivize these behaviors?

Sherry Eckholm: Besides a comp structure that allows for some type of equity? I may be biased here… but a driven and flexible team of researchers, strategists, and designers who speak the language of design thinking and user-centered design. The ability to identify what users need through what they do, not what they say. Actionable insights are not just about delivering customer value; they have to marry with a business model and enabling technology. 

Lastly, and probably the most important lesson for my fellow designers, is that you have to be able to translate insights into a game plan that makes sense for the business. You need to be able to speak the language of business! You have to be able to make the case for why the company should invest its resources. That's why I often joke about getting multiple MBAs during my time at a startup studio!

Gregor Mittersinker: Once you've got a handle on the problem, what is the magic translation to turn those insights into a product-market fit, whether it's for startups or corporate ventures?

Sherry Eckholm: Prototyping. And keep it simple, especially in the early stages. You don't need to go overboard with details and fidelity. Feel free to assemble a rough prototype, even if it's just simple Sharpie sketches on half sheets of paper. When you're talking to people to validate a concept or solution, they need to know that what you're showing them isn't precious but a work in progress. And it allows them to feel empowered to build on the solution. The more polished something is, the harder it is for people to give you honest feedback. Most people don't want to hurt your feelings or call your baby ugly. Timing is everything; no one has the time or money to waste polishing something that will never see the light of day.

Gregor Mittersinker: OK, but often, people are afraid to show rough prototypes because they don't want to confuse the user. How do you manage the narrative at this point? How do you create an early prototype so the user sees the value proposition in something that still needs to be finished?

Sherry Eckholm: The best approach is to listen carefully as you walk through the prototype. You're taking them on a journey and learning from their perspective. This process involves asking open-ended questions, listening, and adapting to their feedback. What do they think this is for? Where would they expect to find something like this? What would they expect it to do? What part of their life would benefit from this? Essentially, you're giving them a platform and prompts to react to. In user experience research, you want to understand how they make decisions, the drivers behind these decisions, and watch out for confusion as they interact with the prototype.

Gregor Mittersinker: You spent six years in the insurance industry, which is one of the most heavily regulated industries next to financial services and med tech. Insurance has its own language and areas of expertise, and it isn't exactly known for innovation. What is your advice in navigating that institutional bias? And how do you leverage user research to make actionable strategic decisions?

Sherry Eckholm: Regardless of industry, you've got to speak the language of business, know the terminology, and understand the various functions and why they matter to the overall value chain. A legacy industry with deep institutional knowledge will only trust your hard work if they are confident you understand the business. If you deliver something that feels like magic and aligns with business expectations, you have a much better chance for success. 

Insurance premiums and coverage are based on data and insights from the past, not current and future trends, so it's no wonder we continue to see customer satisfaction drop. Insurance needs to be able to keep pace with customer expectations. Rapidly evolving technologies in AI, combined with changing weather patterns, wildfires, and more frequent catastrophic losses, are forcing the industry to rapidly adapt to survive. It's an industry that initially feared disruption but is now embracing technology to gain efficiencies, streamline operations, and become more proactive rather than reactive - ultimately making better use of policy dollars. Once these pieces are in place, the industry can innovate new products and services that fit customer expectations better than today.

Gregor Mittersinker: You've successfully worked in a diverse range of industries and settings. When you advise clients on venture building, either as a company or an entrepreneur, when is the ideal time to engage with an innovation and design agency? Why would they want to talk to a design company, and when? And how do you right-size the venture's needs for the agency to still be profitable?

Sherry Eckholm: Ha! Are you asking a design evangelist and serial innovator where clients should put their money? The answer should be obvious! Just kidding - it's a great question. 

As a designer, I jumped at the opportunity to build a corporate startup studio because corporations have the capital to provide startups with upfront human-centered design, something that a cash-strapped startup may have a hard time justifying. And, traditionally designers have two career pathways - corporate or consulting. But rarely do we have the opportunity to experience and assist in creating something entirely new to the world and see it from start to finish.

Even in the corporate world, investing in user-centered design upfront is a smart move. It's the foundation for nailing that product-market fit. Sometimes, a long-term business or design strategy requires a larger investment of time and money. Other times, a few loops of prototype-test-learn are all you need. Listen, no matter how many of your buddies love your idea or how much cash you throw at it, if it doesn't solve a real problem better than the current solution, it's a total non-starter. Understanding your user is gold. When building a new business - whether internally facing or an external startup, you're about to embark on the most important journey of your life. You're going to put everything on the line to achieve success. Wouldn't you want the confidence that you are on the right path, as opposed to just hoping? Seems like money well spent to me!

A big thanks to Sherry for sharing her valuable insights. Her broad experiences illustrate how the designer's toolbox crosses business models and industries. We're excited to have her on board at Loft as we continue shaping meaningful experiences and pioneering ventures. Stay tuned for more insights from Sherry and the Loft team!

About the Author



Gregor Mittersinker


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Austrian-born Gregor is in his element while dissecting most complex business & technology challenges and creating their next level business outcomes.

Prior to starting Loft, Gregor led a Strategy & Design team at Accenture Interactive where he helped launch new multi-billion dollar businesses for global fortune 500 companies. He also led creative teams at Rollerblade, InMusic & Cross.

Outside of business hours he teaches Service Design & UX at RISD, and hosts a weekly think tank with global business & political leaders around the world.

He has worked in the US, Europe & Asia over the past 30 years has earned numerous design awards as well as holds well over 100 patents for product innovations around the globe.

A natural motivator, leader, collaborator, and innovator, the only thing that takes Gregor’s eyes off of design for long is his love for winter sports, kitesurfing and DJing in local clubs.

Many have tried to keep up with Gregor, few have succeeded.

Next level inspiration … Japanese wood craft and joinery, minimalist forms that are functional and proportioned.

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