New Podcast: Why Your People Team Needs a Seat at the Leadership Table

Lindsay Verstegen, SVP of People at ShopRunner, joins us on the podcast this week to discuss how she redefined the company’s mission, vision and values to build employee trust.

Connect with Lindsay on LinkedIn and Twitter.

Follow ShopRunner on Twitter, LinkedIn and Facebook.


































































































Adam Robinson: Welcome to The Best Team Wins Podcast, where we feature entrepreneurs and business leaders, whose exceptional approach to the people’s side of their business has led to incredible results. My name is Adam Robinson, and for the next 25 minutes, I’ll be your host as we explore how to build your business through better hiring.

Adam Robinson: Today on the program, Lindsay Verstegen is the SVP of People at ShopRunner, located in Chicago, founded in 2011 by serial entrepreneur, Sam Yagan. They have 135 employees, on their way to 150 by the end of the year, and are backed by some of the Who’s Who in Venture Capital. We are so excited, Lindsay, to have you on the program today. Welcome to the show.

Lindsay V.: Thanks.

Adam Robinson: We’re going to focus on the people side of ShopRunner today, but before we dive in, let’s set the stage. Give us 30 seconds on ShopRunner and what you guys are doing.

Lindsay V.: Sure, so we have millions of members that we offer free two-day shipping to. You can get that membership by way of paying $79 ala an Amazon Prime model, or lots of those members receive that membership for free through partners like American Express or PayPal or MasterCard. We consider ourselves complementary to Amazon versus in competition, because that would be really silly to think, “Oh, let’s take down Amazon.” It can be done, so to those out there who want to do it, go for it, but for us, we consider it complementary. We’re helping retailers fight their way to relevance in today’s shifting eCommerce landscape.

Adam Robinson: What are some ways for our listeners to better understand what you may offer to retailers, so that they can understand the context for the conversation today?

Lindsay V.: Yeah, so that’s something like we now offer the two-day shipping and then access to … We have over four million members. We have about 140 retailers. Those retailers are both department stores, like a Neiman, or brands, like a Kate Spade. If you think about basically what it is to find your way in the online/offline mix for those businesses, something like two-day shipping and/or thinking through how to get in front of those millions of members and, by the way, because of the strategic partnerships we have, those are members that you want to have. From a demographic perspective, they’re very enviable, a very enviable client base.

Lindsay V.: We are giving the access to those people, and then, what’s happened now … You mentioned Sam. Sam actually didn’t start ShopRunner, but took over ShopRunner in 2016, midway through, and so it’s been a bit of a reinvention of ShopRunner. Call it v. 2.0 or 3.0. I don’t know what “v” we’re on now. Really, where we’re going next is we describe ourselves as providing arms to people in the war. We are giving them options in terms of machine learning or other sorts of products we can build to make them relevant, as people expect more and more from what eCommerce can do for them and how convenient it can be.

Adam Robinson: If listeners want to learn more, what’s the best way for them to do that?

Lindsay V.: Yeah, so they can go to and check us out there. If you have AmEx card, you already can be a member, you just need to enroll, and similar with some of these other strategic partnerships we have.

Adam Robinson: All right, fantastic. Let’s dig in here on the people’s side of the business. You’ve been there since the beginning of 2017. Is that correct?

Lindsay V.: Yep, that’s right.

Adam Robinson: Taking over as the VP of People for an established business with a new leader with, as you and I know, a very specific way of doing things, give us the lay of the land of the organization, as you inherited it, and what the quick hit list was for you, after you had spent 90 days in the business.

Lindsay V.: Yeah, so I walked into a business that had an office in San Mateo, an office in the Philly area, Conshohocken to be specific, and then Sam took over the business with intention to make Chicago headquarters, but it was just [inaudible 00:04:27] and I, the CTO, his head of engineering, and the CFO in an office in 1871. And so this was purely aspirational and a lot of why he did hire me as I’ve had experience at fast growth companies with an emphasis on mission and vision and values. And so when he brought me on, there was this vision that eventually we would look a lot different, but we didn’t really know what that meant and because we were in the business of reiterating on what people knew shop runner to be. It also meant, yeah, we could look at historical context, but it was only helpful to a certain degree.

Lindsay V.: And at some point we needed to shake things up. So we made the decision relatively early on and we had about 70 people at that point, sort of half and half I would say between Philly area and San Mateo. We made the decision to close the San Mateo Office. That was something … Historically, I’ve overseen teams in the three areas you think every company probably is in at that scale, which is Chicago, New York, San Francisco, and so I had had exposure to those other markets and knowing what our mission was, I felt pretty confident that we could find the talent we needed in Chicago specifically. Um, and so we made the decision to close down that San Mateo Office. So that was a really intense start as you can imagine because we had little bit over 30 people there. And then we started what I learned, which was a culture sort of exploration that would culminate in an articulation of what the vision mission and the values would be that would then drive our hiring.

Lindsay V.: So at that point as well, I didn’t really have a team in place. So, I of course needed to find a team, but I also believe that you need to know who you are and what you’re looking for before you start to hire. Some people don’t take the time to do that. They just think, okay, I’ll figure it out as I go. I needed to know at least enough to feel confident I was signing them up for something they wanted and getting me the right person to take it across the finish line. And so once we had the vision, mission, values starting to take shape, I then started to add recruiters, talent partners as I call them, and then started to build up the business on the recruiting front with an eye on how do we then make the rest of the business from a benefits workplace culture standpoint, attract and retain the best talent once we found them.

Lindsay V.: So it was sort of building the rocket ship as you’re flying into the air, metaphor happening for sure. And now at this point we are just under shy of 140 people. And I’d say it’s about two for one. So two people in Chicago for every one person now in Conshohocken, Philly area.

Adam Robinson: So let’s talk … There’s a lot there to dig into. I mean, it’s fascinating to me so that you and a CEO partner take over a business, get involved in leading a business that had history, lots of locations in a culture by default, perhaps not necessarily by intent and the first thing you set out to do is redefine who Shop Runners [inaudible 00:07:48] from a values and culture perspective. So tell us … Give us that map. How did you go about doing that?

Lindsay V.: So I think what you’re talking about with regard to the partnership Sam and I have is key because number one that he made a people pro be a direct line of reporting into him is meaningful. So I’m on top of that, I was actually pretty content where I was at. And so the compelling piece of this challenge was that Sam also wanted to start thinking about diversity and inclusion early. So I had been an organization historically that had their heart in the right place but weren’t necessarily making the actions to progress that evolution in the workforce, supporting women, people of color, et cetera. And so the fact that Sam came to me and that was part of what he’d been thinking about even early, was really compelling to me because I wish that was more common place. It’s not. And so I think that partnership and the fact that Sam and I do see it as a partnership is really key.

Lindsay V.: I think leaders that fail to make their people a part of that leadership team are missing a huge opportunity because it’s often folks in my seat, who have really unique perspective and a holistic perspective, I think that sometimes get shut out. In great organizations, it’s prevalent in this kind of like the voice of the customer, but the internal customer, right? Like, what are your employees saying about you? And so, we took that on and I think the other thing was, as you said, culture by default, that was 100 percent the case. And then I think specifically when you’re thinking about diversity and inclusion, there’s a lot of things that I discovered were implicit ways of operating that became things people expected but weren’t thinking critically about. So it wasn’t about like, is that actually the best way we should be doing it? It was more of, well, that’s the way it’s always been done.

Adam Robinson: Give us, give me an example of that. So what’s one of these things that you went after early?

Lindsay V.: Yeah. So I mean, you think about a leader like Sam and then if you look at my peer set, they’re all impressive in their own right. And so you might think, okay, that’s going to be a top down organization. The organization had been super, super, super top down in the past to the point where I think in the first several months we were challenging people to challenge us because it just wasn’t happening. So, and I think, you know, Sam’s a super smart guy. So part of that is of course you want to hear what he’s saying, but he doesn’t have the perspective someone sort of on the front lines does.

Lindsay V.: So a lot of what we did was one of the values we did articulate was candor. Because that was not necessarily the way things worked. People just kind of did what they were asked to do and sometimes in terms of building what I describe as a builder mentality, the foundation wasn’t there yet because historically the way I did hiring had worked was very, very, very top down. The way you hire has huge implications. I think Andy Dunn of Bonobos describes it the best when he says cultures who you hire, cultures who you’ll fire. I think about that a lot because I think, you know, you can be as aspirational as you want, but the proof is in the pudding in terms of the people actually out there doing the building for you. So we had a lot of work to do with regard to not letting people be stagnant and encouraging people to not wait for the answer to come from on high, you know, to sort of say, hey, you’re in as good a seat as anybody to determine where this business goes. And so that was a huge, huge endeavor we had from the get go,

Adam Robinson: For listeners who are leading an organization or a part of the leadership team and organization where they haven’t been there from the beginning or they’re charged with culture change, is there a philosophical takeaway or lesson learned from your experience that you think in anyone can and should be thinking about as a first step in this kind of thing?

Lindsay V.: Yeah, my take is you want to honor history, but you don’t want to be a slave to it. So, you don’t want to be fearful of operating outside of the parameters of what has been done historically, but you want to acknowledge it. And so what I did was initially start with the group of executives attempt that Sam had assembled. And really, part of it is when you assemble a whole new leadership team, we also are getting to know one another as we’re building our teams. And so I think taking the time to really ensure we were speaking the right language and I think collaborating in a way we felt really good about. So some of the questions initially I talked to the executives about was talk to me about the best team you’ve ever been a part of.

Lindsay V.: So, and the way that this team described it, it wasn’t about the sort of bells and whistles that get a lot of airplay today. It was about we didn’t think we were going to get to the finish line and we did and here’s how. It was about how people bridged together and really sort of set off to solve a problem together and did it successfully. So we started there. And then what happened from there was, as I said, paying homage to history. What I did was assembled three different cohorts of people within the business. Both who had been here for some duration and had seen that history and some people who were pretty new and really made it a diverse mix of people and went in with some specific questions sort of in the vein of what’s the best team you’ve ever been a part of, but also then asking how do things work around here and how do you feel about that?

Lindsay V.: And so it was a series of questions where I think the number one thing you can do is create a safe space where people feel they will be heard and that when you come back and you say, “Here’s what we heard and here’s who we are,” people believe it’s authentic and people believe it’s something they can kind of hitch their star two and move forward. So there may be a lot of uncertainty as you build things, but you’re going to know this sort of internal code of conduct and way that we expect each other to work. That will always be true. So those are the rails as you go down the track. And I think it’s super important to give that sort of psychological safety as well, and that’s where things like vision and mission and values can be so much more than aspirational. It can be just the thing that builds trust within your team.  

Adam Robinson: I can imagine, in my experience, that there are those tenured employees or team members that are highly resistant to the new regime and those that are thinking of themselves thank God finally. We’re doing this differently. What was your experience in deputizing folks with internal credibility who were bought into the new way of doing things?  Did you find you had hand raisers or did you have to search to pull that out given the struggle with top down historical communication flow?

Lindsay V.: Yeah, it was kind of a mixed bag. And I think part of it is I believe you have to be compassionate with regard to change. We’re just human beings. We’re animals ultimately that want to feel safe and that what we’re doing matters. And so I think in a couple of cases where there where people … There are people who’ve put in a lot of blood, sweat, and tears into this business to get it to where it is today. And like I said, there is an acknowledging of that, but there’s also giving people space to absorb the change and to really hear it. And so in a couple of instances, we actually went out of our way to say, “Please take time,” whether it’s a long weekend or whatever. I think we encourage people to take time when it was like it didn’t matter what we were going to communicate. Change is hard. It’s just inherently difficult.

Lindsay V.: The other thing though, and this goes back to hiring is even if people were here, we circled back and we said, “Let’s articulate what your job is,” and it sounds so simple, but as you know, over time and in a fast growing business, the thing you were hired to isn’t necessarily what you’re doing anymore. And so, there was also a discipline brought that included job descriptions. And we even used scorecards with outcome related bullet points that helped keep people focused in the right ways and make it so clear … As clear as we could be about what we thought success looked like in the role they were in. So I think those couple of things helped sort of vet out whether it was, hey, change is really hard, this person is taking the time they need versus you’ve seen it, it’s okay to unsubscribe. And in a couple of cases people to do that and we respectfully parted ways. But only after we took the time to do some of the leg work that is involved. You can’t just say we’ll figure it out and be so ambiguous about what it is. So we really sought to clarify that where we could.

Adam Robinson: Excellent. So you mentioned a couple of sentences there on hiring process and outcome driven job descriptions and those kinds of mechanics for companies seeking to implement a hiring process for one didn’t exist before. What would you say was the biggest challenge you faced and how did you overcome breaking through to the manager ultimately are going to be doing the interviews and making the selections?

Lindsay V.: Yeah, I think a couple of things had to be true, so that means before I had a team, I was offering a level of support that was legitimate. I wasn’t saying again in the same way. I’m not saying, hey, figure it out. I’m saying here’s an example of a scorecard, or here’s an example of a job description or you come up with something and then we will collaborate on what it means and what will make it good and not good. And ultimately what the job description, you’re just ultimately looking to tell the most accurate story so that the right talent it feels, oh, I could do that or that you can put a recruiter on it, and eventually I did have a team of recruiters which was super, super helpful because I am but one person, and they could partner with the hiring managers to really get at what they wanted from it and find the right language to communicate that back out.

Lindsay V.: So not only that, but I think also we did a lot of work similarly. It’s sort of like figure it out as you go along. It’s so tempting because the world moves so fast, but it’s so important to build the space to be intentional and thoughtful. So, even things like even after you have sort of the nuts and bolts seen to, the job descriptions, scorecard, what have you, the things you find effective. Then what about who the panel going to be, what are their areas of focus? And again, it’s not rocket science. It just requires a level of intention and consistency. So you can set the plan, but then how do you execute the planet? Who holds you honest to it? My team plays that role time and time again. And if things change, then we all get on the same page and say, hey, things have changed.

Lindsay V.: We actually thought we wanted this thing, we want this other thing. So I think consistency and process consistency in sort of what are the things we need to engage with you as the talent team on your search. That was also another thing is I think too often, or I’ve seen in many other environments, this frustration between the hiring manager feeling like the recruiters and giving me what I need and the recruiter sitting there going, the hiring manager isn’t giving me what I need. We were super, super clear that in order to engage with you on a search, and we rarely use third parties. In fact, we really haven’t. We say to them, we will partner with you. We will fill this role. We need a job description and a scorecard before you start. And so it makes the hiring manager come to the table with clear expectations of what we need in order to feel like we’re going to do an effective job for them. And so I think just some of those … It’s just discipline I think and a clarity and again, clarity, knowing that you can recalibrate at any point along the way as needed.

Adam Robinson: Now you’re currently managing two office locations. You’ve got approximately 150 people who by the end of this year, which is the point at which most research shows is where the old system of communication starts to break down. It’s this theoretical dunbar number, as it’s referred to. Culture being so important, what tools or approaches or systems are you putting in place to promote a one company culture versus an office based location based culture?

Lindsay V.: Yeah. So what my team now are those recruiters I mentioned, the talent partners I mentioned. I also have a people experienced team. So those are folks thinking about manager training we should bring. Because your managers become the way those tenants either live on or don’t. And again, similarly, like when the business is moving fast, it’s easy to think of the manager. We’ll figure it out. That is true. They will figure it out if you’ve hired the right people, but hopefully we can give them some sense  of what good looks like in your organization. And then the third thing is office experience or the office team. So at the office team we often use this phrase called sisters, not twins, so there are things that in the [inaudible 00:21:35], tradition and again, because they’ve been together longer, we want to be beholden to those traditions.

Lindsay V.: We want to do those traditions because they’re meaningful. It doesn’t mean that we’re going to start doing them if it’s not meaningful for this office, but I think the ways that we connect the dots are we have an HRIS with a social recognition functionality, meaning I can give Kudos to whoever and whatever office and I will be around a specific way someone went above and beyond and just having public evidence to what is being celebrated in hearing about specific ways people are delivering. It is super powerful. I mean, again, we’re human beings. We love to hear stories, so I think finding ways to create a narrative internally is really important. And then the other thing is for each all hands we have, or I should say once a quarter, we do what we call the big cash awards. So we did our values exercise and came up with seven values and then realized at the end, that we can make them spell big cash, which was not intentional but a hilarious byproduct and the only thing now I take the time to say, hey, we didn’t do that on purpose because that could communicate something very weird that like, okay, we want it to spell big cash, but that wasn’t actually what played out.

Lindsay V.: So now we have the big cash awards where someone can actually nominate someone from wherever and hold up one of those values and say this person has grit and here’s how I’ve seen them have grit or this person has hustle, here’s how they have hustle. And then we celebrate that publicly and then give them a little token of our appreciation as well. So I think finding consistent ways to celebrate wins is hugely important because again, stories live on as opposed to talking about it once or hearing about it a lot in your interview and then you never hear about it again.

Adam Robinson: Fantastic. So as we wrap up here, a year from now, if you were to come back on this show and talk to us about whether or not you accomplished the most important or impactful program or change facing your part of the business today, what would you be telling us happened in 12 months?

Lindsay V.: So I would be telling you that our managers are feeling embolden to be super effective managers. I think what happens after you’ve assembled so much of your team and in so quick a time as you’re all trying to recalibrate. And especially for managers, you’re trying to recalibrate as you’re building a team. So I would say that you would in a year be able to talk to anyone who manages at Shop Runner and say I’m doing the best work of my life. I feel like I’m doing the right things for the people on my team. And here are all the tools that my people team provides to me that makes me feel like they got me. And so I think that’s going to look like a lot of different things and I have ideas for what specifically it looks like, but that would be my goal.

Adam Robinson: Ladies and gentlemen, that’s the final word you’ve been learning today from Lindsey Verstegen, SVP of People at ShopRunner based in Chicago. Lindsay, thank you so much for being with us on the program today.

Lindsay V.: You Bet.

Adam Robinson: And that’s a wrap for this week’s episode of the best team wins podcast where we’re featuring entrepreneurs and business leaders whose exceptional approach to the people side of their business has led to incredible results. My name is Adam Robinson, author of the book The Best Team Wins, which you can find online at Thank you, as always, for tuning in. We’ll see you next week.

Narrator: Thanks for listening to the best team wins podcast with Adam Robinson. You can find out more information about Adam and his book, The Best Team Wins: Building Your Business Through Predictive Hiring, at Thanks again for listening and we’ll see you next week.