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Lindsay Verstegen of ShopRunner: “Show up authentically and unapologetically”

Show up authentically and unapologetically. These early innings of my career have in large part been about owning my perspective and liberating others through the realities of every day. Right now people might be reading this and thinking “Wow! What an amazing journey! She’s so with it!” and it has been amazing. But I think […]


Show up authentically and unapologetically. These early innings of my career have in large part been about owning my perspective and liberating others through the realities of every day. Right now people might be reading this and thinking “Wow! What an amazing journey! She’s so with it!” and it has been amazing. But I think my strength is my ability to be vulnerable and real. That means I don’t put on airs about some magic that exists to make it all come together. I have hard days and days where I question myself. But I also believe that my job, as a leader, is to help people focus on the bigger picture and how we find ways to drive to progress wherever we can — not without acknowledging the reality, but rather in acceptance of whatever the reality is. And finding a way to thrive within it!


I had the pleasure of interviewing Lindsay Verstegen. Lindsay has been helping people across successful tech companies — from Groupon, Braintree, Venmo (eventually acquired by PayPal) and now at ShopRunner. At ShopRunner she leads the people team with special care towards creating the very best place to work in every geography in which ShopRunner operates. She and her team have spearheaded various initiatives to create a workplace where diversity can thrive. Lindsay ended up in the people profession from a music and theatre background, recognizing the work as the place for the telling and sharing of important stories, providing a place for powerful connection. ShopRunner has 215 employees that work in offices in Chicago, New York, Philadelphia and Krakow with employees also distributed remotely.


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

It was an accident. I’d love to talk about my one-time “5 or 10 year plan” that brought me here, into a job I love, making a difference I believe in. I’d sound so wise! What I can say is that curiosity and a genuine love of people and the ways they come together brought me to this path. I come with a humble spirit and with a desire to help people live fulfilling lives, energized by interesting work and solving problems that matter. It’s hard to fake the interest I have in people — it’s genuine. I also believe nothing is actually accidental — and that the best things happen when one is open to what the universe reveals. I made decisions based on instincts that I’ve developed over time. I know how to see smart and good people and I gravitate toward them, learn from them and they tend to make the kinds of companies that other people look at and say “hell yeah”

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

I came to ShopRunner because it’s a terrific business and I was, of course, interested in building the kind of company I would delight in telling my kids about someday, but I also came to test a hypothesis that was brewing from my first two high-growth company adventures. ShopRunner was a great place to test a theory that caring about diversity and inclusion is most meaningful and impactful at the early stages of building a company. We have inclusion as one of our core company values and we talk openly about the dynamics that lead to inequality. We are always striving to be open to ways that we can be better, know better, and do better. This is the most diverse team I’ve helped to build and that is, again, no accident. It has come through careful attention to the realities that drive inequality, and conversely, to the intention and solutions that combat it. Inequality leads to products that are built with blind spots that limit their use to consumers everywhere, while equality leads to highly useful and impactful products that address needs comprehensively. Limited perspective drives businesses that aren’t living up to their highest potential, delivering the most value possible, while a broad aperture expands both the potential you can reach and your ability to reach it. A company built with that focus and mindset is the kind of company that my sons will want to hear about — and that couldn’t be more important to me.

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?

This goes back a long ways, but I made the mistake of engaging with a candidate’s mom when I was first recruiting. As a recruiter, you get the amazing job of making people’s dreams come true! You also get the amazing (sarcastic) distinction of rejecting people from jobs they think they’re great for. I consider it a necessity to be up front about whatever outcome plays out. Many, many years ago I rejected a candidate for a sales job and made the mistake of engaging with his mom who followed up to fight me on why I had made a terrible mistake. I never anticipated having to battle it out with a mom, but I did and it was awkward and I really was trying to make her understand but it really didn’t matter and I still laugh about it. Now, with sons of my own, I can honestly say I don’t plan to fight any of those kinds of battles for them.

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

We stand out by leading with our values as we solve a tricky challenge: enabling online commerce through an incredible time of evolution. We do what we can to help retailers and brands remain connected to their customers, all while the ways people connect with their goods and services evolve at the speed of light.

We lead with our values and we do that right alongside our retailers. We recently did a celebration of Pride month with a happy hour where proceeds went to the Trevor Project as well as a local Chicago organization called The Brave Space Alliance. Some of our retailers including Urban Decay, Kiehl’s, Kenneth Cole, Calvin Klein and L’Oreal also found ways to celebrate Pride month and help the community through shining a light on the cause and even selling goods that help progress.

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

We’re constantly evolving to keep up with the changing landscape around us. On the enterprise side, we’re providing tools that will help take retailers into the future. On the consumer side, we’re expanding our core value proposition to provide our 3M+ members with even more value in their Prime-for-the-rest-of-the-internet membership. We’re now offering member exclusive deals and adding some of the world’s best brands spanning every category to our network. Our overarching goal is to amplify the best parts of online shopping and mitigate the maddening parts, connecting customers to brands they love through delightful shopping experiences that meet them where they are. I find that as I navigate life as a working mom, this kind of “meeting me where I’m at” is invaluable. Time is the ultimate resource for me and for so many other women and people everywhere. We’re trying to help make shopping a joy, and one that doesn’t require taking time away from the things that matter most.

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

Show up authentically and unapologetically. These early innings of my career have in large part been about owning my perspective and liberating others through the realities of every day. Right now people might be reading this and thinking “Wow! What an amazing journey! She’s so with it!” and it has been amazing. But I think my strength is my ability to be vulnerable and real. That means I don’t put on airs about some magic that exists to make it all come together. I have hard days and days where I question myself. But I also believe that my job, as a leader, is to help people focus on the bigger picture and how we find ways to drive to progress wherever we can — not without acknowledging the reality, but rather in acceptance of whatever the reality is. And finding a way to thrive within it!

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

Communicate. Communicate. Communicate.

The biggest challenge with scale is effective communication throughout the organization. When things are growing and more people are joining, the effort required to effectively communicate expands. It’s so important that, whatever the stage, people understand how the work they’re doing rolls up into the bigger picture. It’s important that a leader also comes with communication in a way that serves the employees and the audience at large — meaning, again, meeting people where they are at and where the message most resonates and is heard.

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?

I am eternally grateful to a few female mentors I met along the way. There are too many to count and the list includes both strong women who raised me and strong women who came into my life at opportune times. These were women who saw me as a woman with a career but also as a woman trying to navigate early motherhood and spoke to me directly and honestly through it all. Meg Laundry was partner at the recruiting firm I worked at when I first got my start and she saw something in me that I didn’t when she said “you have an innate business sense in you. Someday you will figure out if you want to use that for a higher purpose.” She was neither the first nor the last woman to see potential in me that I hadn’t seen in myself. The best mentors champion, cheerlead and point at potential even before we recognize it in ourselves.

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

I continue to connect with people and connect good people to one other. I look to shine a spotlight on people and groups who are otherwise underrepresented. I have hard conversations with people in power to help challenge assumptions and empower other women to do the same.

Mostly, I advocate for a workplace that allows employees to come to work as their best and most authentic selves. I truly believe this makes them better partners, parents and citizens because we aren’t forcing them to put on a mask to come to work. Authenticity liberates.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

  1. Show up authentically: Sometimes it can feel like being assertive or advocating for your perspective can be so challenging and uncomfortable. The reality is that for every person you frustrate by not aligning with them, you set another free by speaking your truth. Unique perspectives aren’t a liability, they are table stakes to making a difference. I can’t tell you the number of women who have thanked me for being honest about what I needed from work when I came back from having my first baby. My advocacy was fueled by my own vulnerability but it was authentic and I knew advocating for better spaces to pump and better flexibility to figure out the balancing act was the right thing for me and could serve to fuel change that ALL WOMEN needed.
  2. Know your “why” : The world changes and business dynamics change so the ability to be nimble is important. If you’re anchored into a purpose, the agility feels like it’s grounded in your why and makes the ride more fun. In the ways I’ve navigated my career, I’ve always leaned into the places I can have the most impact. It can be scary to leap into the unknown, but it’s important.
  3. Be Present: In this day and age, it’s important to be mindful of one’s own attention span. My biggest disappointments often come from my own inability to focus my own mind’s eye. The best gift you can give your team (or your family) is the gift of attention in a time when distractions abound. (I’m still working on this one every day)
  4. Embrace what makes you different: Instead of apologizing (even if you’re only doing it internally), step into the power you may have as an “other” in the room. Didn’t go to an ivy league school? There’s perspective there. Didn’t have a traditional background? There’s a fresh perspective there. Have insights because you come from a specific part of society that is uncommon? Step. Into. Your. Power. Make your voice heard.
  5. Have fun. The best leaders are having fun even through hard patches. Acknowledge the hard but keep a sense of humor and don’t forget to keep things in perspective. The hardest part of leadership is often managing one’s own psychology and mindset. A strong mindset is the foundation for all of the other things to be done: both at work and in life.

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. 🙂

The US is one of the richest and most developed countries in the world and yet, for families, it’s one of the worst. The amount of energy moms and dads alike spend trying to juggle through policies that are shaky at best and miserable in specific industries is a sad thing. We need paid leave available to parents, childcare support, and better early education available for all. So, if I could inspire a movement, it would be one of compassion centered on driving better parental and early childhood outcomes.

I am working to do my part as a talent leader by shaping policies at each company I join (and letting my competition keep up with the bar we’re raising!) and more broadly within my sphere of influence by giving a voice to this problem and the solutions I am finding to address it. While I’d like to see our country take a stronger stand that families matter, I’m a big believer in being the change you wish to see — so let’s start with compassion and from there, create a more widespread movement that meaningfully changes how we empower and support parents in the workplace.

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

“You are the sky. Everything else — it’s just the weather.” ― Pema Chödrön

This favorite goes back to my earlier statement that all good things stem from a solid mindset, a generous spirit and energy that’s ready to be agile with whatever life throws.

How can our readers follow you on social media?

Follow me at @lindzsays on twitter, opinions my own.

Thank you so much for these inspiring insights!

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