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Shipt CEO Kelly Caruso: “Your team needs to hear from you; Connect with them”

Connect with your team. Sometimes that’s large touchpoints like all-hands meetings or professional development, but it can also be smaller opportunities like small group lunches or coffee meetings. Your team needs to hear from you — whether it be in person, over video messages, or Slack. As a part of my series about strong female leaders, I had […]

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Connect with your team. Sometimes that’s large touchpoints like all-hands meetings or professional development, but it can also be smaller opportunities like small group lunches or coffee meetings. Your team needs to hear from you — whether it be in person, over video messages, or Slack.

As a part of my series about strong female leaders, I had the pleasure of interviewing Kelly Caruso, Chief Executive Officer of Shipt, Inc. Kelly Caruso is a seasoned retail professional with vast experience in retail merchandising, technology, and sourcing. In March of 2019, she became the Chief Executive Officer of Shipt, a leading online same-day delivery marketplace. Under Caruso’s direction, Shipt offers delivery to more than 250 markets and 80 million households nationwide. The company also has a network of more than 100,000 Shipt Shoppers. Caruso’s experience in the retail sector spans 25 years with companies such as May Merchandising, Abercrombie and Fitch, and Target. Prior to joining Shipt, Caruso was the Senior Vice President of Merchandising for Hardlines at Target. During her time at Target, she led numerous merchandising teams within Apparel, Accessories, and Home. She also led a multi-national team responsible for the global sourcing of Target’s Owned Brands in Apparel, Accessories, Home and Hardlines. Caruso is a member of the board of directors for the Network of Executive Women (NEW), and is an alumnus of the Studio E Entrepreneurial Leadership program in the Twin Cities. She received her BA from the University of North Dakota. Kelly and her family have relocated to Birmingham, Alabama — the Magic City.


Thank you so much for doing this with us Kelly! Can you tell us a story about what brought you to this specific career path?

I graduated from college with an accounting degree during a recession in the early 90s. I really liked the financial side of the business, but I knew that I didn’t want to be an accountant. I took a job as a buyer at Yonkers department store in Des Moines, Iowa. I really loved that job because it was rooted in both art and science, and retail is just that. After twenty-three years at Target, where I’ve had the opportunity to leverage experiences in creative design thinking, insights and analytics, and leading a global team, I was given the opportunity to transition into the role of CEO at Shipt.

Can you share the most interesting story that happened to you since you began leading your company?

The transition to leading Shipt is a brand new chapter for me — it’s all interesting! In particular, I spent over 20 years working for a Fortune 50 company that was out of its startup phase long before I got there. Shipt is just exiting the startup phase and I’m excited to be a part of that. I’m leading teams that are smaller and I’m learning to work in a smaller, scrappier environment. Navigating a business without the longstanding history has been a challenge, but it’s one that I welcome. We’re building the history of Shipt and our industry as a whole right now and that is so very special.

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

There are many mistakes I’ve made over the years and those stories are part of what shaped me into the leader I am today. I believe in the power of a mistake to change your thinking, improve your skills, and keep you humble.

What do you think makes your company stand out? Can you share a story?

I was able to experience Shipt for the first time as a member, and more importantly, a wife and mom on a snowy Saturday in Minnesota. Grocery shopping has always been a part of my Saturday routine, and on this particular day, the weather was less than lovely and I just couldn’t imagine getting out in the snow, sitting in traffic, and braving the elements just for groceries. In comes Shipt! I placed my order at 7am and by 9am, my groceries and essentials were in my kitchen and I was cooking brunch for my husband and my sons. For me, that time was priceless. From then on, I was a Shipt evangelist. In addition to an amazing experience, we give the gift of time to our members.

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

The retail landscape has changed so much in recent years, and we don’t see that changing any time soon. There is a significant amount of market share up for grabs in the same-day delivery space. According to the Food Marketing Institute, online grocery sales are predicted to capture 20% of the grocery retail overall by 2025. That’s predicted to be $100 billion. There was another poll in the summer of last year that stated that only 5.5% of grocery purchases were made online. You might look at it as small market share, but I look at it as big opportunity. Shipt has a clear mission — simplifying lives. We want to increase the number of members — and with increased demand, we’ll need more shoppers, too. We are expanding the assortment of items we can bring to our members so they increasingly see Shipt as the solution for every need. Because sometimes you need a cantaloupe and an iPad– and you need them at the same time. We want to launch in new markets to bring same-day delivery to more consumers. We’re spreading the Shipt love to even more areas of the country. And of course, we plan to add new retailer partners to make our marketplace even more valuable to our members.

What advice would you give to other female leaders to help their team to thrive?

I truly believe the attributes of a good leader are the same, whether you’re male or female. First of all, it’s important for leaders to ensure they have a purpose-driven strategy to engage hearts and minds. The mission is crucial, but so is the buy-in from the team. It’s also important to be a servant leader. It’s your responsibility as a leader to remove the barriers that stop your teams from doing their best work. Finally, be a good steward of a company culture that is strong. If you have that, foster it! If you don’t, be the agent of change to develop that culture.

What advice would you give to other female leaders about the best way to manage a large team?

In my opinion, the best leaders, male or female, excel at these things:

  1. Connect with your team. Sometimes that’s large touchpoints like all-hands meetings or professional development, but it can also be smaller opportunities like small group lunches or coffee meetings. Your team needs to hear from you — whether it be in person, over video messages, or Slack.
  2. It’s important to have multiple feedback touchpoints in place so you can keep a pulse on how your team is feeling.

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

One of my first bosses at Target went on to be a mentor and a sponsor of mine for over 16 years. Early in my career, she took a chance on me and granted me a promotion because she believed in me, even though other candidates might have had more experience or might have checked more boxes. She was a coach and a developer for me, but she was also a truth-teller. When she provided feedback to me, it was often tough to hear, but it came from a place of caring and understanding. When I became a parent and I was learning to navigate in a two-working parent household, she became a role model to me in a new realm. When she left the company, she made a recommendation that the team name me as her replacement and that propelled my career forward. She was a teacher, an advocate, and a friend to me.

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

For me, it has been so important to advocate for equality in the workplace, especially as it pertains to gender. I care deeply about creating cultures that are diverse and inclusive. Where there is good diversity, it leads to better business solutions and it elevates the entire team. I also believe that diversity without inclusivity is not the end goal. Creating an environment where people can bring their most authentic self and their best self to work every day is what I enjoy. Having the opportunity to create that culture and have that impact is what I enjoy most about my job.

You are a person of great influence. If you could inspire 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. 🙂

Equality and inclusivity are so important to me. If you think about it, it’s truly holistic and essential to the success of our society. We can improve upon that early in the journeys of our youth. Kids need teachers, mentors, and role models that look like them. They need a relatable perspective from someone to show them that with hard work, they can be anything they want to be.

I’m also very passionate about food and the role it plays in our everyday lives. Shipt focuses its giving efforts largely on hunger and food insecurity. When it comes to youth development, food is representative of so much. It provides a sense of security. Their access to food is often determined by where they live. We have a powerful tool that puts food in the hands of those who want and need it, so we’re doing our best to be good stewards of that and give back to the communities where we operate.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

”It is what it is.” For me, ensuring that I don’t ruminate on things I can’t control allows me to remain focused on solving problems at hand and moving forward. My journey has been sprinkled with really great times and other times that have tested me. Knowing that “it is what it is” keeps me grounded and calm.

Thank you for all of these great insights!

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