Kimberly Inskeep of cabi: The Future Of Retail In The Post Pandemic World

An Interview With Jilea Hemmings

Jilea Hemmings
Nov 14 · 20 min read
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Retailers are focusing more resources on existing customers vs. gaining new ones. This strategy has been critical for us. At cabi, our Stylists have a very loyal client following and during these uncertain times, we have been hyper focused on retaining and rewarding their loyalty, whether through high-touch communication from their personal Stylists or exclusive promotions in which we provided “gifts of gratitude” as a thank you for supporting their Stylist’s small business.

part of our series about the future of retail, I had the pleasure of interviewing Kimberly Inskeep.

Kimberly Inskeep is the CEO of cabi, a women’s fashion apparel company, which has been selling solely through Independent Personal Stylists for almost 19 years. Believing there could be a better way for women to both shop and work, Kimberly was instrumental in the testing, development, and initial launch of the innovative cabi Fashion Experience and Stylist career opportunity. She oversees all aspects of the Stylist organization. Prior to joining cabi, Kimberly spent several years working in finance and international management consulting with BlessingWhite, Inc. and Norwest Corporation (now Wells Fargo & Company).

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

was really by accident.

The person who eventually became one of my business partners asked me if I would want to help him out with an idea he’d been thinking about. He and his wife had run a mid-size women’s apparel company for about 15 years and were tired of the same old circles they would run with the big department stores as their distribution channel. He wanted to find a way to go directly to the customer (long before e-commerce) and wondered if women would buy direct from one another. He told me they had past-season garments at their factory and I should come by to consider what I could do with them. So I went to the factory, loaded a truck with 3,000 garments, my husband racked our garage with PVC piping, and I sorted items into outfits and laid them around my living room. I invited groups of women over, about 8–10 at a time, put out a bit of food and drink, and let them try things on. At one point, I found a group of about 6 women in one of our bedrooms sitting and laying on the floor in their underwear, sipping champagne I had served, talking and laughing with one another. They looked at me and said, “If we could shop this way all the time, we’d never go to the store again.” And I knew we were onto something! Weeks later, I was asked to partner with the husband and wife team to pursue this idea. I remember saying “Why me?” and his response was, “Why not you?” And in that moment, I felt unbridled and released to run after something I knew could be really big.

Can you share the most interesting story that happened to you since you started your career?

Doing the thing I said I would never do, never imagined, nor ever wanted.

Since the inception of cabi, I’ve never wanted the role of CEO. I’ve loved being “one of the founders” and as an entrepreneur, I’ve wanted to retain the role of idea person with talent for seeing opportunity, the challenger who’s not fearful of risks, and the relentless trailblazer who would help the company accomplish what others hadn’t. Where I’ve always been okay with uncertainty and willing to put more on the line, most CEOs are focused on the financials and their big payout in the end. Additionally, the focus on straight-line planning, implementing, and integrating strategic direction to meet financial goals seemed to be at cross purposes with maintaining an entrepreneurial culture.

About three months prior to my planned retirement, our CEO moved on and I was asked to step into this role. The surprise of my career — I said “yes.” And along with a mature and exceptional leadership team, I have embraced and enjoyed the opportunity to learn and develop the skills to become a fully-efficient, effective CEO…while not losing the entrepreneurial tendency to act on promising opportunities, embrace calculated risk, and stimulate a culture of curiosity. Entrepreneurs can be CEOs and CEOs can be entrepreneurial.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson or takeaway you learned from that?

Letting men name a company that’s for women.

My husband and I were at dinner with my business partners (the husband and wife team). She and I got up to use the restroom and when we returned, the two men had come up with the name for the business: “Home Merchants Group.” It sounded like “Home Depot,” which is a fine name for a building supply store, but not a women’s fashion business. We used the name for about five months and then decided we would take over the naming of the company.

Lesson learned: a company for women needs to be led by women.

Are you working on any new exciting projects now? How do you think that might help people?

There are two exciting projects that come to mind first — one that helps women experience personalized styling sessions with their very own personal Stylist through our proprietary virtual platform, called cabi Front Row; and another initiative that is creating a ripple of goodness around the world through our charitable foundation, called The Heart of cabi Foundation.

The core of the cabi experience is in-person styling sessions — a group of friends enjoying time together with the support of a Stylist providing styling tips and personalized help. As you can imagine, it’s a ton of fun! As we sought to serve our clients even more flexibly when, where, and how they want, we endeavored to build a digital environment that achieved much of the same fashion-centered magic that an in-person gathering did. The goal was also to enable our Stylists even greater flexibility — working when, where, and how they want.

We began building this proprietary software, cabi Front Row, 18 months ago, bringing it into beta testing about one year ago — and you can imagine how fortuitous it was to have a platform ready to roll that enabled our Stylists to go from primarily in-person events to primarily virtual when the pandemic hit. While other retailers were scrambling to come up with new ways to reach their clients, we transitioned immediately, escalating our rollout with 2,500 of our U.S. Stylists using it with clients within four weeks. The speed and smoothness of this shift was partially the brilliance of this new technology and partially because of how our Stylists have built such strong relationships with their clients over time.

It’s been incredible to bring our signature relationships-first approach to an online experience. Clients are invited into an interactive space, alongside a group of friends, all in their remote locations where they can connect through video and chat. Our Stylist is at the core of this experience, and she provides styling ideas and personalized help while the guests view beautifully shot runway videos where they can easily “like” pieces as they’re shown. Those “likes” create a virtual dressing room from which to make shopping decisions. The Stylist is available to answer any questions, help with fit, size, color, fabrication, and help create wardrobe capsules. Beyond fashion advice and service, this experience has also provided community — time with girlfriends that is greatly needed (perhaps especially during this pandemic).

The second project I’m especially energized by falls within the work of our Heart of cabi Foundation. We never wanted to be a business seeking to be successful for success’ sake, and we always wanted our success to be a way for us to do good for others. Our 15-year-old foundation does a number of things, including donating clothing for women in need domestically and internationally, supporting women entrepreneurs in the developing world through our one-for-one small business loan program through Opportunity International, and supporting education in Rwanda, and it’s that last piece I’ll talk about now.

Through a number of trips we’ve taken with Stylists to Rwanda to meet women entrepreneurs we support, we saw a clear need…one we could relate to as mothers. The motivation behind all of these women’s business goals is to provide a strong education for their children and empower them to break the cycle of poverty. And so, we saw a need we believed we could help fill — we decided to channel our Make a Change funds (donations from clients who generously round up their orders) to support school fee loans and school improvement loans across Rwanda — alleviating the financial stress on entrepreneurial mothers, as well as elevating the quality of the school facilities. It’s been amazing to join hands and make a huge generational impact in this part of the world.

Atul Tandon, CEO of Opportunity International, cast a powerful vision for us that the potential to eradicate extreme poverty in the world really is possible within our lifetime — if people like us commit to the solution. It’s been very satisfying to see poverty rates continue to diminish. In Atul’s words: “Cabi is sparking transformation at the bottom of the economic pyramid. I’m forever grateful for cabi’s partnership, support, and encouragement.”

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

This is the million-dollar question right now. For many businesses, including ours, every person on the team mustered all of their energy and creativity to get through those first six months to keep business going, exerting themselves at levels that aren’t sustainable. I think there are a few critical aspects to continuing on without everyone running themselves into the ground. And not just keeping just shy of burnout, but actually living healthy, fulfilling lives — even amidst the pandemic.

The first aspect is physical — the discipline of taking rejuvenating breaks. So often our brains tell us to just power through, while our bodies say “enough.” And we must listen to our bodies. This might mean a quick walk, choosing to go to bed early and pick the project back up in the morning, choosing to take a full day away from your computer to spend time outdoors, or choosing to have tech-free dinners with family. With smartphones and watches, it can feel impossible to ever peel away. But we must, or we’ll crash and burn.

The second aspect is mental — we have to shift our mindset. When working very hard with an overfull to-do list, it can start to feel like drudgery…unless we see our current problems as a fun opportunity to learn and provide meaningful solutions. Years ago, when I lamented to a colleague about the mountain of problems I needed to solve, he said to me, “Kimberly, that IS business — business IS solving problems.” That reframing was a game changer. We’ve also adopted a two-part phrase at cabi that’s simple, yet powerful: “This is hard AND this is fun.” We acknowledge the discomfort of being in challenging territory, but we also invite that fun energy that comes when you’re learning a ton through trying things that might not work, but wow, wouldn’t it be cool if they did. This reminder that solving problems is fun breeds innovation, risk-taking, and a drive to push through to realize that thrill of victory. This is a posture that welcomes disruption and keeps us in that scrappy and agile entrepreneurial state of mind, even almost 20 years into our business.

The third aspect is emotional — we need to take care of one another. The vast majority of the workforce works interdependently among a team. When that team commits to investing in relationships, engaging with each other empathetically, stepping in for one another sacrificially when life gets hard for any team member, a life-giving community takes shape. These types of teams are safe spaces where they genuinely enjoy and value being together. That dynamic alone can provide huge reserves of energy.

None of us are able to achieve success without some help along the way. Is there a particular person to whom you are grateful, who helped get you to where you are? Can you share a story?

Building a business is not for the faint of heart and often costs personal relationships. A spouse or partner can make or break your spirit in the pursuit by being either an advocate or an adversary. There were moments in the early days when it seemed like my husband and I had exacted every ounce of tolerance from one another and there was nothing left. My preoccupation with the business and his lack of understanding for what it takes to build a new company meant our initial united advocacy for a great idea turned adversarial and we began to resent one another. Both of us wanted something from the other and didn’t get it. Through some wise counsel, we were challenged to flip it around and go into each day seeking to see what little thing we might give rather than get that day — things as simple as space and grace, and thankfully, things began to turn around. The person who advocates, challenges, encourages, redirects, gives me painful and positive feedback, and talked me into continuing on even after retirement was delayed, has been a significant part of my success and I’m deeply grateful. I’m so grateful for how the tension points have made us stronger and wiser.

How have you used your success to bring goodness to the world?

From the inception of cabi, we knew this business would only be worthwhile for us if we created a lasting impact on the lives of women, and we dreamed that would also include women all over the world. It’s been a deep joy to see how that’s happened.

The core of our business brings goodness to women’s lives every day through the transformative power of our clothing and our game-changing entrepreneurial opportunity. We see it loud and clear — when women feel empowered, phenomenal things happen. And with that truth in mind, over 15 years ago, we created The Heart of cabi Foundation to “empower women in need.”

We’ve donated over $59 million in clothing domestically and internationally. Whenever a domestic natural disaster strikes, we seek to be of service by re-wardrobing women who’ve lost everything. We also partner with organizations that support women transitioning out of vulnerable life circumstances, like homelessness or domestic abuse. Our cabi Stylists have been the hands and feet of love, working one-on-one with women to help them find just the right pieces that make them feel beautiful that they take home for free.

We know that when a woman receives an open door of opportunity, she can take hold of it in a way that not only changes her life, but her family and community as well. We see this with our cabi Stylists. And so, it was a perfect extension of our desired impact to partner with Opportunity International, creating the very first one-for-one microlending opportunity for women — whenever a new cabi Stylist builds her business, we provide a small business loan in her name for a woman in the developing world through our W.E. are cabi Program; over 17,000 loans have been given to date.

Because we’re all about relationships, we’ve taken multiple trips with our Stylists to Rwanda, as I mentioned earlier, getting to know some of the incredible women who are truly changing their nation through the businesses they’re growing because of the loans they received. We couldn’t help but look for more ways to contribute, and a consistent refrain we heard from women we talked to was that their first financial goal was to support their child’s education. And so, we created a program that directly supports education in Rwanda, as I mentioned before. Rwanda is rewriting their story from one of tragedy to one of victory, and we’re humbled to play a role.

Our foundation work is active in 62 countries — bringing goodness and life-changing opportunities to countless women and their families. And we have great expectations for deepening our impact in the future.

Ok super. Now let’s jump to the main questions of our interview. The Pandemic has changed many aspects of all of our lives. One of them is the fact that so many of us have gotten used to shopping almost exclusively online. Can you share five examples of different ideas that large retail outlets are implementing to adapt to the new realities created by the Pandemic?

In our business, we are constantly reading, doing due diligence, and studying the macro environment, especially in light of the pandemic. We look at trends, consumer buying behaviors, shifts in marketing strategies, and of course we go straight to the source, listening to our loyal clients. All of this directs how we think about the positioning of our sales, marketing, and growth strategies. Over the last 5–7 months, there are five key trends and ideas we have been watching most closely, some of which retailers are beginning to implement in order to adapt to the new realities.

  1. Providing live, online/virtual styling sessions.

I read an article recently that shared how Levi’s and Tommy Hilfiger are turning to live, online sessions hosted by influencers and celebrities, especially in an effort to appeal to the consumer who may be wary of returning to the store. This concept is similar to what we set out to do with our cabi Front Row platform, which has allowed our personal Stylists to take our signature experience of providing in-person styling experiences guided by their expertise and provide it in a seamless, virtual environment. Our cabi Front Row styling experiences, similar to what Levi’s and Tommy Hilfiger are doing, have allowed our Stylists to style and serve their clients virtually in a highly personalized way, and in our case, deepening ongoing relationships with clients.

2. Retailers are focusing more resources on existing customers vs. gaining new ones.

This strategy has been critical for us. At cabi, our Stylists have a very loyal client following and during these uncertain times, we have been hyper focused on retaining and rewarding their loyalty, whether through high-touch communication from their personal Stylists or exclusive promotions in which we provided “gifts of gratitude” as a thank you for supporting their Stylist’s small business.

3. Investment in SMS/text messaging.

The concept of text-based commerce has surged during COVID-19, as consumers are spending more time than ever before on their screens. This strategy allows brands to break through the ever-increasing noise that’s hitting consumers’ inboxes and reach consumers where they are — their mobile phones. Brands like Burberry, Kenneth Cole, and others are testing the waters with texting to deliver just-in-time promotions or exclusive access to insider tips from sales associates. At cabi, we’re finalizing a text messaging platform, allowing us to communicate with our loyal Stylist and client base in a new way, a new methodology we suspect will have a warm reception due to how we’ve invested in those relationships all along the way.

4. Focusing on personalization.

Brands are challenged, more so today than ever before, to stay connected and engaged with their customers, and focusing on personalization is key to doing this well during the pandemic. Rag & Bone has done this well by pivoting to offering virtual, one-on-one personal styling appointments with their store sales associates to offer curated recommendations. Many companies are upping the ante on shoring up data insights to provide personalized ad targeting. At cabi, our Stylists offer the benefits of personalized help in the moment, but often times are also working from a well-founded relationship that has built over time.

5. Rethinking the customer experience with a focus on human connection.

More than ever, consumers are looking for human connection right now, and successful retailers are the ones that are finding unique ways to deliver connection in this remote/virtual environment. I read that Kiehl’s is offering digital skin care consultations. Vogue recently reported on the rise of “squad shopping” where experts are creating platforms for friends to social shop together virtually. For us at cabi, human connection is at the core of everything we stand for and deliver to our clients. Our desire is to provide highly personalized fashion styling experiences that ultimately bring women together with their friends, either in person or virtually. Women think of our product and our community as a combined entity — cabi is both fashion and community, and that’s why thousands of women choose us again and again.

In your opinion, will retail stores or malls continue to exist? How would you articulate the role of physical retail spaces at a time when online commerce platforms like Amazon Prime or Instacart can deliver the same day or the next day?

I absolutely believe physical spaces to buy product will be around in the long term, although they will likely look quite different than they do today. Traditional mall formats with jammed turnstiles and insufficient customer service will surely die off as the race to the bottom of better-faster-cheaper reaches a natural end. And yet, we are tactile, experiential, and social creatures — wanting to show up in person and engage with people and environments is core to our beings.

The showroom concept we’ve been seeing more and more of in recent years will likely continue — a space where people can experience and interact with product with the help of a knowledgeable expert and then place a product order. People crave experiences, and we’re wired to want to connect with people to help guide and affirm our choices. (People also spend more in person than they do online.)

So why do we shop so much online (barring the uniqueness of these pandemic times)? We think it saves time and is more convenient. Schlepping to a store seems like a greater time demand in the mind of the consumer, but in many cases, Internet trial and error ends up being a greater time suck with endless searching, no experts to interact with, and inevitable returns. In the long run, getting to touch and experience the product, learn from an expert and ask questions, and even build a relationship with that person that continues in the future saves time ultimately. You actually get what you want and need. Digital can certainly still play a role — at cabi, we have a virtual platform that provides an experience and live expert support that is proving to be a valuable complement to a physical experience.

The category where Amazon Prime and Instacart are winning is quick-use consumables. You don’t want to wait a week or reroute your day to go pick up the dishwasher soap you’re out of or the chicken you need for dinner tonight. But when it comes to products you’re inviting into your life and home to stick around, consumers know the right product is worth the wait. Just look at how many months people have shown they’re willing to wait for a Peloton after shelling out a few thousand dollars — a company making great use of the showroom concept.

What we’re seeing, of course, is not a binary choice between physical and digital — smart retailers recognize that consumers want both in a seamless, omni-channel experience supported by technology. Amazon’s ultrafast Prime Now grocery offering is now complemented by Amazon Go, tech-enabled physical grocery stores. Instacart is just a conduit between the consumer and a physical store. Consumers want the choice of in person and online, and most often use both.

The so-called “Retail Apocalypse” has been going on for about a decade. While many retailers are struggling, some retailers, like Lululemon, Kroger, and Costco are quite profitable. Can you share a few lessons that other retailers can learn from the success of profitable retailers?

Relevance is the key to any business’ success, and in a lot of ways, the recipe for relevance is unique to every brand and product category — it’s the amalgamation of thousands of little decisions. Lululemon, Kroger, Costco, and many others are successful for many different reasons including cashflow, branding, and product strategy, but more than anything, they are relevant.

There are two rules of thumb that go across categories to maintain relevance:

  1. You must always be willing to change HOW you do business and WHAT you sell.
  2. You must stand firm in not changing WHY you do business.

On one hand, you can never rest on your laurels. What draws consumers today may very well not drive them tomorrow. You might have product development, delivery, and technology dialed in, but consumers may want each of those to be different tomorrow. You must stay in close relationship with the consumers and hold none of your “top products” or “best practices” sacred. Top companies are in touch with consumers and agile to make quick changes.

On the other hand, relevance is unequivocally wedded to the WHY of your business — and it’s the part of your business that doesn’t change. If your reason for being doesn’t meet a relevant need in the hearts and lives of people, you’re sunk. This is the bigger purpose that will be as real today as it is 20 or 100 years from now. This is where your business plays the infinite game versus the finite game (ideas popularized by Simon Sinek). At cabi, why we do business is to affect lives through relationships. As we grow and evolve into different product categories, like adding jewelry or providing virtual shopping environments, that doesn’t change.

We can all think of the once-iconic Blockbusters and Pan Ams and Borders Books and Compaqs of the world that appeared to have staying power. They either failed to change how they did business and what they sold, or they changed their purpose — or didn’t have a strong purpose to begin with.

Amazon is going to exert pressure on all of retail for the foreseeable future. New Direct-To-Consumer companies based in China are emerging that offer prices that are much cheaper than US and European brands. What would you advise to retail companies and e-commerce companies, for them to be successful in the face of such strong competition?

Few companies could stand a chance of out-Amazoning Amazon. And if that’s their goal, they’re destined to fail (there’s certainly a reason why Amazon was named after the biggest river in the world!). But there is no reason to cede ground to Amazon, believing consumers will always value their offering more than yours. The better-faster-cheaper competition reaches a natural end. Consumers value more than free, quick shipping. They’re also willing to pay for quality products and service…if you find a way to matter to them.

Amazon’s model is to cast a wide net — total market domination, selling everything from A to Z to every consumer on the planet. And yet, there’s an opposite and highly viable business model where the goal is to matter more deeply to fewer people — find a select audience, serve them really well, and they’ll pick your brand every time. At cabi, our personal Stylists offer one-on-one personalized styling advice, reaping the benefits of ongoing human connection with every purchase. And human connection doesn’t scale in the way Amazon approaches business, so despite their behemoth size, we’re not threatened by them.

When Amazon (or other retailers with their eyes on market domination) cater to the masses, set your sights on a select group of followers, and give them all the humanity that Amazon can’t.

Thank you for all of that. We are nearly done. Here is our final ‘meaty’ question. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I’m passionate about facilitating human connection in a world where connection has been replaced by technology.

We’re living in an interesting time, where technology is king, but when it comes to what really contributes to emotional and mental health and life fulfillment, relationships are king. We need community, and yet isolation is currently a health epidemic and technology is a large culprit. Not only is it a time suck, but it has changed the way we communicate, stripping away empathy and connection, text by text. The nature and depth of our interaction has become something totally different. Our connections have gotten broader, but more shallow. So it’s no wonder people feel alone. And while we may think “That’s not me,” who among us can avoid the ways we engage in more efficient modes of communicating and the way the world functions with less and less actual community? We’re becoming complacent with the illusion of relationships that demand very little emotional labor from us…and yet we know something is missing.

In the social sciences, there’s a phenomenon called “clusters” — small communities of people who impact each other — and then there is a ripple effect where those individuals impact the people in other circles they’re a part of. Within cabi, I’ve dreamed of starting “cabi Conversations,” dinners that happen all around the country, centered on intentional dialogue from which thoughtful communities are born — clusters of connection where we reclaim conversation, relegating technology to what it does best (communicating information), and using our human skills for what we do best (connecting and building real relationships).

How can our readers further follow your work?

While much of my work is published internal to the cabi community, you can find my work on the HuffPost and cabi blog, and I’m also on Facebook and Instagram as @kimberlyinskeep.

This was very inspiring. Thank you so much for joining us!

bout the Interviewer: Jilea Hemmings is a staunch believer in the power of entrepreneurship. A successful career revamping Fortune 500 companies was not enough for her entrepreneurial spirit, so Jilea began focusing her passion in startups. She has successfully built 6 startups to date. Her passion for entrepreneurship continues to flourish with the development of Stretchy Hair Care, focusing on relieving the pain associated with detangling and styling natural black hair. For far too long, people with tender heads have suffered in pain. Until now.

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Jilea Hemmings

Written by

CEO & Co-Founder at Stretchy Hair Care I Author I Speaker I Eshe Consulting I Advocate For Diversity In Beauty

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Jilea Hemmings

Written by

CEO & Co-Founder at Stretchy Hair Care I Author I Speaker I Eshe Consulting I Advocate For Diversity In Beauty

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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