Description: Maynard Webb, has been CEO of LiveOps, COO at eBay, and chairman of Yahoo’s board. Now this Valley veteran has written Rebooting Work: Transforming How You Work in the Age of Entrepreneurship. He’ll join veteran corporate technologist Jeremy King to talk about how to grow and sustain a business now.


The following transcript has been lightly edited and condensed for ease of reading. 

Speakers: Jeremy King, Walmart |  Maynard Webb, Webb Investment Network

Moderator: Stratford Sherman, Accompli

(Transcription by RA Fisher Ink)


Sherman: We’re here with two people who have been in relationship with each other professionally and personally since 1995, and we’re here to talk about how relationship and help in learning and development end up being important in your career. And by the way—

Webb: Most people couldn’t put up with me for that long, but Jeremy was willing to do that.

Sherman: A gracious man. These aren’t just any two people, though. Jeremy is CTO of Walmart, which is in the middle of a gigantic e-commerce push that Jeremy is leading. He has probably one of the largest budgets in IT on the planet, and he’s dealing with an organization in Bentonville, Arkansas that was probably not totally oriented toward the things you are doing now in its past history, so there is what you might call a degree of change going on here.

King: Absolutely. Yes, Walmart has gone through a digital transformation really over the last seven years. There’s a new book out called Dual Transformation that I was just reading, and if you took out all the business terms in there and added “Walmart” it would be exactly what’s going on. We have a core business that’s great, we have a leadership team that knows how to run a million-person organization and execute incredibly well. And for the last seven years or so we’ve really redoubled our efforts on e-commerce and the omnichannel play. It wasn’t too long ago that all e-commerce players were saying that physical retail is dead, and now everyone is essentially chasing our model because that’s really what people want: they want the digital-physical experience put together. So the digital part of that, the technology transformation, has been what I’ve been focused on. We have great teams in Arkansas, in Sunnyvale, in San Bruno, in Bangalore, and around the world that are working this 24/7.

Sherman: So Jeremy, how do you keep from getting fired?

King: You know—people ask me this too—CTOs are going to get fired, right? I mean, you cannot go into it and—

Webb: You have never been fired, right?

King: I have never been fired, yes, luckily.

Webb: So I wouldn’t freak about it too much.

King: Yes. People worry about security breaches, websites going down, budget issues, that sort of thing, and I think the secret to managerial success and leadership success is being incredibly transparent about what you are doing. One of the things that we’ve done with our teams is we have turned everything around. When you have such a large budget and a large team, how do you tell the organization what you’re working on, what’s important, what’s the highest priority, and who is working on the right things? As we focused on online grocery we moved all of our best teams and leaders to online grocery as we focused on that in the company, for example.

Sherman: Maynard, you’ve got a book out called Dear Founder, which I highly recommend. It’s one of the most insightful compilations of pragmatic leadership advice I’ve ever seen, and what’s so great about it is that it’s about half questions. That’s something I notice in you, Maynard, just as a thinker, you seem to be asking more questions than providing answers. How does that work when you are in relationship with somebody who is less experienced than you?

Webb: Well, I think I’m always looking for potential, and growing potential, and I have to say that I had a delightful experience of running into Jeremy—I don’t know how old you were—but he was a lot younger, and I was lot younger, and he was the only one at Bay Networks—I had just joined as a CIO and I wanted to build—this sounds quaint now—but I wanted to build the world’s first intranet and show the technology. We had a bunch of other projects on the plate, and I asked my whole staff at the howl organization, “Does somebody what to come do this as a special project with me?” The only hand that was raised was Jeremy’s, and he didn’t give up his day job, he did his day job and we worked after hours to go build this, and it turned into a very successful project.

Sherman: So that raises the question for both of you: how do you decide who is worth investing in? Are you Johnny Appleseed just throwing it to everybody, or do you pick?

Webb: You pick.

King: Yes, you pick. I think people in general—and Maynard and I have had a great relationship—but I try and spot myself in that conversation. Now that I am in your role, how do I find the other Jeremy’s who are volunteering, who will give pretty good insights? They can be relatively young. I have a group of mentees at Walmart and all my companies, and I am oftentimes getting more out of it than they are, because I understanding what’s going on in the organization, how they are feeling about leadership changes. I can bounce ideas off of them, so it’s less about picking somebody who is up on the chain than somebody who is willing to talk to you about what is going on in the org.

Webb: I think it’s finding somebody who is willing to volunteer. That’s not the only thing; they have to have the competency so you have the confidence that if they do it they can deliver what you’re hoping for. So there is more to it than just somebody raising their hands. Jeremy had a very good reputation and had been breaking snow already and I thought, “This could be interesting and good.” Then I just keep trying to give him more to see how far he could go, and now look at him.

Sherman: Any advice for young people about how to attract your attention? How do actually elicit this kind of guidance and support from you?

Webb: The biggest piece of advice I have is to go volunteer to do things that are hard and that are broken, and not force it into a job discussion that you leave your current job. Just go volunteer. There’s more stuff to do than any of us can do, so people love—

Sherman: Keep your day job and solve the problem.

Webb: Yes, go solve it. That’s how I got started in my career. I always did extra credit stuff.

King: I tell people who ask me how I got to where I am—and Maynard and I have talked about this a bunch—it’s really finding people who have a great work ethic. These are things I learned from my parents and my grandparents, and those things are what I’m looking for: people who are going to go above and beyond and really do something extra.

Sherman: So at this stage of your career, when the CEO comes up to you and he puts his hand on your shoulder and says, “This is the most important thing in the entire company. You are going to make or break the company based on this,” how do you react?

King: You know, I have heard that speech so many times.

Sherman: Awesome! [LAUGHTER]

King: We were talking about this earlier. Those kinds of things don’t really bother me anymore, because companies pivot and change, and there are lots of famous quotes. “Change is never going to be this slow again” is one of the great quotes. You have to be ready, and I’m glad that they are coming to me, because you have to be able to absorb that change yourself and figure out what is going to happen with your project priorities, but also how to message it out to the organization, because oftentimes a big shift and change can be disruptive. “What about this project we were working on, is that not important anymore?” Messaging it out, especially for a large team, there are always a hundred priorities.  How do you make sure you are making time to execute well and to get to the number one project.

Webb: One of the biggest things is how do you keep the rest of the things that you’ve already committed on the rails and try to absorb this new—can it be absorbed? So part of that is how do you try not to have everything go guardrail every day on different ideas and still do the ones that are the most important. It’s a fine dance.

King: Yes. At Walmart, we purposefully said we are not going to use the term ‘legacy’—a legacy platform. We call it ‘current.’ This is the current system, it is running our billion-dollar operation. Billions and billions of dollars are going through these systems. We’re transforming and we are modernizing many of these systems, but that is not the legacy system, that is what is running the shop every day.

Sherman: One of the themes that’s been coming out in many of the discussions during this conference is leading with responsibility, dealing with the long-term perhaps unintended consequences of the technology that we’re working with. In a capitalist system that is driving pretty much everybody toward short-term performance and “look out for number one,” look out for not just yourself but your organization, how do you think about the larger, long-term social responsibility?

Webb: Well, first of all, if you are Walmart, you have hundreds and millions of consumers that depend on you every day. When we were at eBay, we had hundreds of millions of people running their businesses on us. As technologists, you have to understand the ecosystem around which you live and you have to have responsibility around what you do with that. I also think it’s way harder today than it ever has been to lead companies, because you are expected to do so much more, and you need to be on 24-by-7. We need to make sure that technology is neither good or bad, but that we actually do our best to make sure that it’s used ethically for the better good of society. That isn’t always something we had to worry about in the early days.

Sherman: How do you get people three or four layers away from you in your organization to be thoughtful about this? Is that even possible?

King: Yes. Fundamentally, I tell my team in many leadership discussions, the business teams aren’t going to come and ask you for a system that’s secure or fast or scalable. Those things are fundamentals to technology. The business team isn’t going to say, “Hey, I want you to build this system, but make sure it’s fast,” right? Or, “Make sure it stays up all the time.” Those are responsibilities of the technology organization of how to incorporate that into our day-to-day life, and as we build out all sorts of new technologies, a lot of people like to talk about AI and ML and what’s going to happen—those things today are being talked about at Walmart like electricity. It’s a given, given our size and our scale, the amount of data that we have, all those projects are essentially fundamentally using this next-generation technology. So it’s going to be part of the core, and that’s effectively how I think about it.

Sherman: I think we’ve got time for a couple of questions. Can we get a mic runner and lights?

King: Awesome.

Sherman: Who knew? Have we go one? Over here.

Audience 1: Hi. My question is for Jeremy. You guys are benchmarking against Amazon, obviously, and Amazon is well known for their experimentation approach, how they experiment on everything. We’ve been tracking Walmart as well. You guys have a great program. Can you speak to how you have used experimentation and data science to drive your strategy and your growth?

King: Yeah, sure. One of the reasons Walmart Labs is named Walmart Labs, even though it’s a relatively large lab, is because I do want all of the teams to effectively run this way. When we created Walmart Labs seven years ago, we essentially created small, dedicated teams that were experimenting on things like social, and we built our search engine and our ad engine and our platform to run SEO and SEM, and that is essentially what we’ve done with Walmart Labs on top of it, so every quarter we have the traditional “here’s the core project” list, and we obviously have the pretty typical hack days and that review sessions for that, but we’ve also kicked off a number of initiatives that I would say are longer-term. For the near-term—one to two years out—Walmart Labs handles that. Then we’ve created, under Marc Lore’s organization, a team called Store 8. Store 8 was sort of a throwback. Sam Walton used to experiment in Store Number 8 with a lot of different technologies, so that team has been focused on things like VR and things that are further out, and we’re giving them the freedom to experiment without having day-to-day P&L responsibilities.

Webb: But Jeremy, I would also guess that it’s not enough to just try to have parity with whatever Amazon is doing. You have strengths that they don’t have, and you need to be able to leverage those and do all the other things, don’t you?

King: Yes, and like I said before, it’s really about leveraging our store network. When you think about Walmart, we need to be number one in omnichannel retail, right? We just launched things like Easy Reorder, the easy return process. If I bought in the store, I know that you bought in the store, and if I come back into the store—if you’ve returned anything at any store, you know it can be an excruciating process.

Sherman: What’s the scale, Jeremy? How many items are subject to easy return?

King: Every item, effectively. Every item—millions. Millions. Every item on and that you buy in the store are Easy Reorder. You just go on your phone. You say, “I want to return this item.” When you walk into the store it’s a 30-second process. Actually it’s under 30 seconds—it’s a 20-second process to return an item. These are the kinds of things that Walmart can be really great at—online grocery pickup or delivery. We have 4,000 mini warehouses all around the U.S. within five miles of most Americans. We get that item to you. Whether you are in Muskogee, Oklahoma or in San Francisco, we can get that item to you.

Sherman: So you feel competitive.

King: We’re competitive, yes.

Sherman: Any other questions? Here.

Fung: Hi. Mei Lin Fung, IEEE and the People Centered Internet. Yesterday we heard from Salesforce’s Tony Prophet—he’s chief equality officer. Walmart having a really huge change on the communities that it operates in, for me the Amazon question begs this question, which is can you be a leader in supporting women? Women are probably your prime customers, and what’s—

Sherman: That’s a question right there.

Fung: No, no, I just want to finish. Tony Prophet said that they actually have a measurement for every manager, how many women are promoted, how many women are part—

King: Yes, we have that as well. Marc Lore’s goal is to have 50% of the leadership team in the eCommerce group to be women by—I think it’s another two years that we have. We set it for four years, and it’s already been two. I do think—not only does Walmart have a majority of associates who are women in the stores, but in the technology play, “How do I make this more personal for Walmart?” So we’ve not only done all the work that you would expect from a corporation to do—sponsorship for girls who code programs and elementary and middle school programs to get girls to stay in STEM for longer, but we’re also working with a couple of groups. There is one I’m really proud of, it’s a company called Path Forward. What this organization does is it takes women who oftentimes have left the workforce to raise a child for a few years and brings them back in. If you leave the workforce for three years and you are a technologist, the world has changed by the time you come back, so how do I give you an internship-like program to bring you back into the workforce as a director? You may leave the workforce as a director and come back in, so I can jump back in as a director. Oftentimes you will see women come back in a lower level job, and we really want the leaders to come back into the organization. We’ve been working with this group Path Forward, and we have about 35 women who are going through the program right now. I’m really excited about expanding those kinds of programs.

Sherman: Last question. In my conversations with each of you I’ve been struck by how—not so much about how technologically competent you both are, although you obviously are—and how organizationally competent you are—although you obviously are—but how humane both of you are in your orientation. The way you think is surprisingly people-oriented and values-oriented. How do you get that out of people, out of other people?

Webb: Do you want to go first?

King: Well, Maynard and I have worked with so many people. As a matter of fact, the first set of associates that I brought on to Walmart Labs were lots of ex-eBay folks, as you can imagine. The network is super strong, and one of the things that Maynard has done, with the WIN work that you’ve done, is keep the network really close—people that we’ve worked with before, like-minded technologists. We talk about work hard play hard, but it’s also having an organization—most people who have worked with me know that that’s my style—we work pretty hard and we expect that from an organization, but we’re going to be out, whether it’s in Arkansas or in Sunnyvale, we’ll be out at the pub having a beer with each other afterwards. I think those kinds of experiences of building teams that are together for a long period of time—we’re very happy to see people come in and stay for three years in a sort of Silicon Valley cycle, but most of my organization, my leadership team, has been with me a lot longer than that due to the tight relationships.

Webb: And I think on top of all of that, we also put a premium on helping people achieve their potential. Once your employees know you have their back—that doesn’t mean you’re going to be easy on them—but that you are investing in them and that you expect them to do great things, and that you will help them figure out how to do it, it all gets better. Unfortunately too often managers and employees don’t have that relationship, so the more you can have that the better it all gets.

King: Yes. There are a lot of good lessons in that book. All the people who are on my team are in the biggest jobs that they’ve ever had, and by definition my job is as well. Walmart is a huge place. But those lessons aren’t just for start-ups. Those are leadership program sessions, and I think you can really get a lot out of many of those.

Sherman: We are out of time. One piece of advice for everybody in the audience, whether locally or streaming is find yourself a mentor like one of these guys if you possibly can. Thank you both.

King: Thank you.

Webb: Thank you.