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2021 Top Women in Grocery Trailblazer: Shipt CEO

Kelly Caruso describes how diversity informs her vision of leadership, what it’s like to head up a tech company, and more
Gina Acosta, Progressive Grocer
2021 Top Women In Grocery Trailblazer: CEO of Shipt
Kelly Caruso (Illustration by Jason Seiler)

Since becoming CEO of Birmingham, Ala.-based Shipt in 2019, Kelly Caruso and her team have grown it into a leading same-day grocery delivery marketplace, scaling to more than 5,000 cities, tripling its membership, adding more than 300,000 shoppers and partnering with more than 120 retail partners – much of this during a catastrophic pandemic. Caruso has more than 25 years of retail experience, holding roles in operations, supply chain and merchandising. Before taking over as CEO of Shipt, she was SVP of merchandising at Minneapolis-based Target. Prior to that, she was president of Target’s independent global sourcing business, supporting the company’s owned-brand growth. Earlier in her career, she held a number of merchandising and inventory planning roles at Target, May Merchandising, and Abercrombie & Fitch.

PG: Did you ever think, while at the University of North Dakota, studying accounting, you would be leading one of the world’s top grocery delivery companies in 2021? Can you talk about why you decided to pursue a career in retail and how your career has evolved?

KC: I did not! But what I did know at that time was that I did not want a job as a CPA.  I had an interest in design and travel, and wanted a career that had both a creative and a numbers side.  I also knew that I wanted to be part of a family.  Retailing allowed me to do that in a way that accounting didn’t. Throughout my career in retail, including my time at Target and now at Shipt, I’ve been able to live a life where I can have a career that feeds my soul with art, travel, design, different cultures and new ideas. And importantly, this career gives me the opportunity to focus on being an executive, a mom and a wife. Having a career that supports that balance is critical, and it was part of my value system early on.

PG: Can you talk about some of your early career influences, who they were and what lessons you learned from them?

KC: Early on in my career, I had examples of the type of leader I wanted to be, but also the type of leader I did not want to be. I had bosses that were not inclusive and who prioritized style over substance. I learned early on the power that leadership can have in creating cultures that people thrive in. That has stayed with me – I have always wanted to create inclusive, creative environments that allow people to thrive and reach their potential. A sense of belonging and fulfillment are also incredibly important to me. When I was at Target, I learned the importance of fostering a culture that allows everybody to bring their most authentic selves to work. It’s important to the culture, but it’s also important to the business. Engaged team members from a diversity of backgrounds contribute more and think more creatively as a whole.

PG: Retailing was a male-dominated industry when your career began. Were there female role models that you looked up to early on?

KC: I’ve had two sponsors in my career, both of whom were women. They advocated for me when I wasn’t in the room and gave me opportunities to stretch myself. But equally important, they told me hard truths. Because I knew it was coming from a place of trust and respect, I embraced their feedback and was able to learn and grow, becoming a better leader.

Progress is not linear, however. Due to the pandemic, women’s participation in the workforce is at the lowest level it’s been in the last 30 years. It’s on today’s leaders to ensure we’re supporting women to stay in the workforce and to provide those opportunities. I’m proud that Shipt has a number of female leaders that younger women and men in our organization can look up to. That progress was earned, and if we don’t put a re-energized focus on this, coming out of the last year, some of that progress could be lost.

PG: Target, which owns Shipt, has done so much for the causes of diversity, equity and inclusivity. Talk about what’s being done to move the needle on diversity among senior leadership at Shipt, but also at other levels to ensure that there’s a strong pipeline of diverse female talent.

KC: I believe that creating a diverse and inclusive culture is not only essential, but also what is best for our team members and for the business. By “diversity,” I’m referring to both diversity of ethnicity, gender, and sexual orientation, as well as diversity of thought, experiences and worldviews.

To me, an inclusive culture means that everyone in your organization feels they are able to bring their most authentic self to work. It means they have a true understanding of purpose – it’s what gets them out of bed every morning. That includes clear rules of engagement, what’s acceptable and what’s not. It means more honest conversations.

We are laser-focused on keeping diversity at the forefront of all we do at Shipt. It’s always been ingrained in our culture, but in the last year we’ve taken steps to formalize processes to ensure equitable seats at the table for our team. As a seven-year-old company, we’re still at the beginning of the journey.

We’ve done a number of things over the last couple of years to further diversity at Shipt and in our communities, including increasing the diversity of our executive team, our tech team and the entire Shipt team. This year we’ve launched Shipt’s first employee resource groups, which include groups dedicated to our diverse team members and allies. We’re also investing in the diversity and equity of our home city of Birmingham. We’re engaged in a local program called VITAL, which exists to ensure locally grown businesses are engaging with diversely owned vendors and suppliers, and we’re investing in Birmingham Promise, which offers college scholarships for Birmingham City Schools students, and apprenticeship opportunities at local companies like Shipt.

The last year has been difficult for all of us, but we recognize it has been especially challenging for communities and people of color. Our leaders have worked to create spaces and programs for our team members to reflect on what’s going on in the world around us, including acts of violence and hatred against the Black community and the AAPI community. In these instances, it can’t be “business as usual” – for us, we seek to meet team members with empathy and flexibility through employee assistance programs, days of reflection, and extra time off to help team members unplug in a way that’s meaningful for them individually.

PG: At Shipt, how do you remove barriers for women and other groups to advance?

KC: Each and every day, we remain focused on advancing diversity and inclusion in all aspects of our business, and at Shipt, women are at the heart of our business. Many of the Shipt Shoppers across the country are women, and in households across the country, many women are making the purchasing decisions in the home, so it’s important that we can understand and relate to the most common needs of our people. This means it is imperative that we have diversity at all levels – first, so that our team members can see themselves reflected in our executive team and understand that there are career and growth opportunities right here at Shipt, and second, to fully unlock the power of mentorship. I believe that mentoring relationships can be even more powerful when grounded in a shared understanding and a relatable background. I’m excited about how we are bringing that to life at Shipt to create trust, respect and deeper relationships that can unlock professional and personal development for our team members in a meaningful way.

PG: How would you describe your leadership style, and how was it developed?

KC: There are three pillars at the core of my leadership: being values-led, being approachable, and caring for our employees, shoppers and customers. I’ve really embraced this approach by being authentic, vulnerable and letting my guard down. By taking note of different approaches and mentorship styles, I’ve discovered a leadership identity which is core to who I am and enables me to show up as my best, most authentic self.

PG: How do you strive to inspire others, to instill a spirit of helpfulness and service in Shipt employees that drives success?  

KC: Everything we do at Shipt is guided by our purpose – to spark the connections that show why every person counts. This lays the foundation for a business rooted in relationships, trust and care, which is what truly sets Shipt apart.

To me, an inspiring culture means that everyone in your organization feels they are able to bring their most authentic self to work. It means they have a true understanding of purpose – it’s what gets them out of bed every morning. I believe strongly in creating this kind of workplace for each and every individual at Shipt.

PG: How has your average workday changed due to the pandemic?  

KC: As a company founded in Birmingham, with an office in San Francisco and retail partners all over the United States, we were adept at leveraging remote tools well before the pandemic hit. Given this existing use of these tech platforms, we were able to seamlessly take our work fully online, all while rapidly scaling our business to meet the growth in consumer demand. While our teams are slowly beginning to return to the office in person, tools such as Slack and Zoom will continue to be a part of our culture and toolkit.

Although it was not difficult to functionally adapt, we’ve made high-impact changes to our culture to ensure employees feel valued, productive and engaged. Early on in the pandemic, we recognized the reality of employee burnout and implemented wellness initiatives to provide support, including incremental days off when the office is closed, no meetings on Friday afternoons throughout the summer, a day of observation on the anniversary of George Floyd’s murder, and a day of service for Juneteenth.

PG: What do you consider to be the most essential keys to food retail success in 2022 and beyond?

KC: Coming out of the pandemic, more than ever, consumers are craving experiences. As the world reopens and we’re faced with the choices of what we’ll return to doing, companies who prioritize the customer experience will continue to thrive.

For Shipt, this translates as a need to continue to prioritize the connection between shoppers and customers as well as our retail relationships. Over the next year, our team is focused on both expanding our capabilities for retailers and adding new verticals to our marketplace, including national, local and regional retailers, and deepening our existing retailer relationships so we can continue to grow our businesses together.

PG: What one new retail trend do you believe will have the biggest impact in 2022, and why?

KC: While it may seem obvious coming from my point of view, convenience will be king for consumers in the coming years. Last year saw an unprecedented spike in the demand for same-day home delivery. While the COVID-19 pandemic initially fueled this growth, indications are that online shopping and fast delivery are here to stay; same-day delivery services like Shipt are no longer a “nice-to-have,” but rather a must-have. Shipt was the resource individuals relied on to stay out of public spaces and keep others safe, all while keeping the household running. In addition, our customers have found value in the convenience and time saved through using Shipt, and we anticipate that will remain the case even as pandemic restrictions are lightened.

PG: Can you share how technology and supply chain solutions are changing the way we shop?

KC: At Shipt, we’re constantly testing and looking for new ways to diversify and grow our business with the latest technology and fulfillment solutions. Shipt is in the early stages of a test in Minneapolis to help Target deliver packages to local Target guest doorsteps daily. In this test, Shipt picks up a batch of packages destined for a specific neighborhood from a sortation center and delivers them to guest doorsteps. In addition to increasing efficiency, this innovation lowers the retailer’s cost to serve all while providing an amazing experience for the customer by infusing the human element to an otherwise contactless transaction. We look forward to seeing how this innovation helps us grow in 2021.

This test is one of the many ways we’re focused on reaching and connecting with more people through Shipt, as well as building a differentiated business in the industry. Connection is at the heart of all we do at Shipt. While we’re always looking for new ways to innovate and be more efficient, we believe that technology without human connection is not relevant for the future.

PG: What are the most rewarding and most challenging aspects of being a woman CEO in food retail and tech?

KC: Only 8% of CEOs are women, so the privilege I have to serve as CEO is not lost on me, and I don’t take it lightly. As a woman in my role, I have the opportunity and the challenge to create pathways for other women who want to forge a similar path.

As CEO, I prioritize three things: I work with Shipt’s leaders to bring our purpose and values to life, I challenge our team to root all that we do in strategy, and I invest in nurturing the amazing talent at Shipt.

It’s been difficult at times to look around and realize that I am the only woman at the table. But in those moments, I remind myself of what a challenge and an opportunity I have as a female CEO to ensure that I’m doing what I can to get other women to the table.

PG: How do you inspire your workforce to be innovative and inclusive?

KC: At Shipt, we believe that technology without a human component isn’t relevant for the future. This is why we maintain a trusted community of more than 300,000 personal Shipt Shoppers who provide an unparalleled experience for our customers.

Over the past few years, as we have expanded our marketplace of goods to connect consumers directly with the fresh foods, kitchen goods, wellness products and essentials they need the same day, the personal relationships between Shipt Shoppers and customers have only strengthened. For example, customers can build their cart and place the order days to hours in advance of their scheduled delivery time, allowing their Shipt Shopper to review and then ask any questions in real time while shopping the order, to cater to any substitutions or product preferences.

PG: What advice would you give to a Shipt Shopper on their first day?

KC: It’s an accomplishment to become a Shipt Shopper! Our recruiting team is incredibly choosy, only onboarding three out of 10 shoppers who apply. That’s because we know that Shipt Shoppers are our secret sauce.

Even before they deliver that first order, we know that Shipt Shoppers will go above and beyond for customers, shopping the way they’d shop for themselves.

So, knowing all of that, I would encourage shoppers to be themselves, shop for their customers as if they were shopping for their own family, and let their personality and attention to detail shine through.

PG: What advice do you have for women climbing the ladder in retail and tech?

KC: There are a few pieces of advice I would give to anyone looking to advance their career. First, know your personal why. This means knowing your personal value system and making decisions about your career through that lens – it will help you find work and an environment that is meaningful to you. Second is to surround yourself with people that know different things and come from different backgrounds than you do. When I’ve been put in roles outside my comfort zone, I develop and lean on a network around myself to learn and grow alongside the job opportunities I was given. Finally, be an ally. Know what allyship and sponsorship look like, and what they mean. This has been incredibly important to me, and I would not be where I am today without the help of so many great women and men who coached, developed and led me along the way.

PG: Who are Shipt Shoppers? What communities and lifestyles gravitate toward becoming a Shipt Shopper?

KC: Shipt Shoppers are a reflection of their community – men, women, racially diverse and belonging to a wide range of socioeconomic backgrounds. What makes shopping with Shipt special is the ability to work as much, or as little, as you like – we find that everyone from parents to college students embraces Shipt shopping to create a flexible channel of income.

PG: What is your proudest accomplishment?

KC: I’m so proud of the work we’ve done to create a dynamic, diverse team at Shipt. The fact that the majority of our executives are women means something, not just to Shipt Shoppers, but broadly to women in business and young professional women. We no longer have to say that it can be done hypothetically; this is our reality at Shipt, and we’re proud of it. We wanted to create a company where team members could look to their executive team and feel that it reflects them.

PG: Do you believe same-day delivery is the future?

KC: Yes, I do believe that last-mile delivery services will continue to fuel both retail and grocery growth, whether the fulfillment be same-hour, same-day or next-day. It will certainly look different based on the retailer, but the demand from consumers is what is crucial, and will drive Shipt’s future success.

From the early days of Shipt, we placed a bet on the power of the personal shopper. We’ll continue to scale and to innovate, but we’ll keep connection at the heart of all that we do.

PG: How do you work with your grocery partners?

KC: Shipt exists to enhance the retail experience, not replace it. We care deeply about being good stewards of our partners’ brands and an extension of their in-store experience. Our team takes great pride in ensuring a mutually beneficial relationship with our retail partners. We put great care into building these relationships and work to find solutions that meet each individual retailer’s unique needs.  Each retail partner we work with has a dedicated partner success manager who is backed by an entire cross-functional team within Shipt to ensure full support of our partner’s business. We provide our retail partners with data and insights into their Shipt marketplace business and take a collaborative approach with our partners in order to drive the business. And of course, Shipt does not share data or insights about retailers with anyone but that retailer.

PG: How did COVID-19 impact your business?

KC: Since the onset of the COVID-19 pandemic, Shipt has experienced substantial growth. We rapidly scaled to now serve more than 80% of the U.S. and more than 5,000 cities nationwide, and have grown our shopper community from 100,000 to 300,000 to meet this exciting increase in demand and need. In the most recent holiday season alone, Shipt witnessed order volumes increase 200% compared to 2019’s holiday season. We’re excited to further fuel this growth as we enter this post-pandemic phase.

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