How Lands’ End Built a Scalable, AI-Ready Procurement Operation
Lands’ End shares how a lean, three-person procurement team transformed fragmented, manual processes into a modern, end-to-end operating model. In this conversation with Raindrop, leaders from both organizations walk through how defined yet flexible workflows, centralized contract visibility, and intelligent automation enable better decision-making across procurement, finance, and the business. The result is a single source of truth that scales with the organization today—and lays the foundation for an AI-powered future.
We’ve got the whole 30 minute for you to watch, but if you’d just like to jump to a part that is relevant to what you are looking for, check out the shorter clips below.
Highlights from the Session
Lands’ End opens the conversation by revealing how behind-the-scenes procurement decisions directly influence customer experience and store margins. Dwayne Waltz, Senior Director of Enterprise Procurement, introduces Lands’ End’s lean, three-person team and the broad scope of indirect procurement—from IT and facilities to distribution and travel. This chapter sets the foundation for how Lands’ End manages the full, end-to-end contract lifecycle and why modern processes and automation are essential to operating efficiently at scale.
Ward Karson, COO of Raindrop, and Dwayne Waltz of Lands’ End explain how clearly defined yet flexible workflows transformed procurement into a business-wide capability. Dynamic intake forms route requests automatically, adapt to different contract types, and evolve as roles and needs change—without slowing the business. With shared visibility into renewals, request throughput, and vendor decisions, teams get the views they need while finance and leadership gain confidence that spend and risk are aligned to strategy.
Lands’ End outlines its next phase of procurement modernization, centered on integrations, supplier collaboration, and AI-driven insight. As the company connects Raindrop with SAP, its new ERP, and key legacy systems, the focus is on creating a seamless, end-to-end experience. By bringing suppliers into the platform and applying AI to contract analysis, risk identification, and trend detection, Lands’ End is positioning its lean procurement team to make faster, more informed decisions—while continuing to rely on human expertise where it matters most.
Dwayne Waltz explains the operational reality Lands’ End was facing: highly manual procurement processes, fragmented data spread across email and shared drives, and limited visibility into contracts and terms. As knowledge walked out the door and information became harder to access, the team found itself reactive instead of proactive. This chapter highlights the tipping point that pushed Lands’ End to seek a modern procurement platform—one capable of centralizing data, reducing risk, and enabling faster, more informed decision-making.
For a procurement team of just three, the impact of Raindrop has been transformative. Lands’ End now processes hundreds of travel, capital, expense, and renewal requests each year, while managing nearly 4,500 contracts in a single system. With a true single source of truth, the team has shifted from reactive firefighting to proactive planning—delivering clearer insights, stronger reporting, and greater confidence for senior leadership decision-making.
A supplier perspective highlights a common challenge: managing multiple contracts across changing teams on both sides of the relationship. With turnover and fragmented visibility, even well-intentioned notifications and optimization opportunities can get lost, creating the feeling that renewals or changes “sneak up” unexpectedly. This chapter underscores the opportunity for stronger collaboration through shared line of sight—where customers and suppliers operate from the same source of truth—enabling more proactive communication, smoother transitions, and better long-term partnerships.
Lands’ End & Raindrop — Full Transcript
(edited for clarity)
Shannon: I’m excited you’re here today to talk with us about procurement. I’m Shannon. I’m from Raindrop and I’m joined today by Duane Walze Walls, who’s the senior director of Enterprise Procurement at Lands’ End. We all know Lands’ End as an organization that provides comfortable and functional clothing. We’re actually wearing our Lands’ End vests today that we found and ordered quite quickly. I was actually pretty impressed by the whole process, but we’re gonna really talk about something that isn’t talked about, which is really how the back office functions really can impact front store margins.
Duane: Thank you Shannon and Ward for having me. As she mentioned, my name’s Duane Waltz. I’m Senior Director of Enterprise Procurement at Lands’ End, leading the team for our indirect procurement function. It’s a relatively small team, we got a team of three. So leveraging tools and process automation and lean processes is really important for us. For a little bit of perspective, indirect procurement, well, what I found out is that Land’ End defines buckets a little bit differently than some other retail organization. So I thought it would be good to share that. Lands’ End defines our indirect procurement, uh, from a category standpoint, covering facilities, IT-related spend, distribution center, DC operations, uh, travel. Those are the categories that we cover within our indirect procurement, uh, process and what we’ll be talking about today. Um, all of those purchases, if we manage the process and everything from intake to the review, the negotiation, the contract execution to the PO standpoint, that entire kind of end-to-end process is what we’re gonna be talking about today. So all of that involves contracts and what we’ll be referring to.
Shannon: That’s great. I remember when we were actually talking and prepping for this one, I actually remember you telling me it was the first year that you didn’t get pulled from your office to go to the floor, to actually go to the distribution center and have to pull things out, which I loved. But you were talking about how you had all of these challenges, both internal and external challenges that you had, and I’d love you to talk about a few.
Duane: Yeah, so that conversation seemed years ago. So 2025 was full of challenges for everybody externally. We were all impacted by the political environment, from tariffs to, uh, high interest rates, shaky consumer confidence. All of those things make it more difficult for leaders to make decisions.
So all of that kind of set the stage for the broader macroeconomic impact.
What can you control and what can’t you? Those are the things impacting us. We can’t necessarily impact those, but what can we control? We can control what contracts, uh, where we take advantage of those risks or opportunities in that market. The only way we can do that is knowing where we have flexibility in contracts. We were gathering information requests from people via email, and it was through a number of different tools. And the different business units might have had different processes. So you have information gathering information and storing that in emails, on POs, on different SharePoint, on different OneDrive. I’m assuming that’s not unique. We’re not unique in that. My prior companies, I was at the, pretty much the same thing. All of those processes are very time consuming, not just to push it through the process, but to go back and, and answer questions when people are trying to dig into it.
Challenges included limited visibility into contracts where we were consistent or inconsistent in terms and conditions. We had, uh, individuals, subject matter experts, risk. As soon as an individual leaves the organization and they knew about that contract, that knowledge in most cases went with them. Even if it was stored on their local machine, that machine was probably wiped in a relatively short amount of time. And you’re not gonna track that back. So those were a lot of the key challenges that we had. It was a very manual process, very difficult. Getting to the data, uh, information was very fragmented. You couldn’t consolidate and analyze it. Um, you wouldn’t move quickly. You were always reactive. There was nothing proactive about it. So that led us to the point of looking for a new tool and looking for, uh, a better way of doing things.
Shannon: And what were some of those goals you were trying to achieve?
Dwayne: Yeah, so, so those are all the problems. The goals as we define them, were to get to a consistent process across the organization. We want everybody sending information in, in the same process and in the same tool. So we can collaborate across the organization. We want, uh, we want the data gathered and stored in a way that makes it common and easy to use for everyone. So that data is not just for procurement, and it’s not just for legal, it’s for the business and to understand what we have in contracts. And in a lot of cases, you’re gonna have business leaders that are turning over as well.
And when they have an incumbent or somebody new coming in to replace them, you know, they need to be able to access that contract and understand what some of the prior negotiation terms were, what the, uh, key objectives were in the original, uh, negotiation. So we wanted common, common and easy to use data, uh, repositories. I mentioned the individual risk we wanna try to mitigate. Uh, we had cases where individuals would store all of your contract data, whether it was, you know, the renewal terms or, uh, could be inflation clauses or cost limits on contracts.
They were all stored off in spreadsheets. Well, spreadsheets, individuals move on. How do you know that even though spreadsheets weren’t subject to somebody keying data in or not finger something in there. So how do you mitigate some of that, uh, key subject matter expert risk? And then, uh, finally the ability to get visibility into contracts across the organization.
We had a lot of businesses buying or negotiating with vendors in their own little silos. Leadership had no ability to see visibility across the board. So when you put all those contracts in one tool, you can start seeing where, and we’ve, (~0.5s) we’ve seen this most recently. There are a number of vendors that, uh, primarily on the software side might have had multiple contracts with different leaders across the board, (~0.4s) all potentially with different terms. So this gives us one common, common repository for that.
Yeah, I love that. And you also gave me a really good example while we were talking about how the different parts of the organization need to interact together and how they do that better now (~0.9s) by marketing influencer example. Yeah. So, so a couple things. Not all contracts are created equal. So talk about the scope of the work that we’re talking about. We’re talking IT facilities, marketing, travel, some of those different pieces. Uh, the example that Shannon is mentioning is some contracts you may have a shorter window to negotiate or opportunity of time to execute that contract and move forward.
Some of them you might have a longer, uh, a longer tail on the front end or a longer notification to get to that. But having a tool in a common process allows some of those contracts. As an example, in marketing, consumers can be very fickle and they might move from one influencer, one marketing approach might have a different impact than another. So signing what those individuals might have, a shorter runway to get that contract executed. The ability to have a process that’s flexible, flexible and yet works through all of the different channels across the organization.
If we’re gonna market, are we gonna have all of the products available? Can the DCA actually ship those? Do we have all of the other pieces? Is everybody aligned on the impact of signing that contract and the ability to push it through quickly? That’s something that we’re getting we continue to refine within Raindrop, it’s giving us the ability to, to make sure that everyone is aware and you have the approvals or the awareness set up within, within the process so that everyone’s included.
Shannon: You don’t wanna be disappointed during the holidays when your influencer told you that great thing to buy and you can’t get it. Thanks Dwayne. So Ward, I wanna turn to you and have you actually chat a little bit about some of the things that Lands’ End actually implemented with Raindrop.
Ward: So as Dwayne outlined there challenges were, siloed data kind of separation, geographically or by, functional towers or by different aspects of processes.
And what we sought to do was to kind of give unified, uh, capability of saying, well, I’m a stakeholder. I want to go buy a good or a service. How do I get that process started? Okay, well I need some intake solution, some orchestration, so that it now democratizes the data and it goes to the proper resources and it flows the workflows. So Raindrop, not a shameless plug, but a small piece of our total solution is a powerful workflow engine.
And so it allows for different types of workflows or who it has to go to for requesting. So now Dwayne could have somebody in the business saying, I want to go buy a widget. I can get that thing going now. I could go have a request for, uh, capital or OPEX request, uh, or travel. That’s a space that’s kind you cover. And the ability to now have those requests go out and get managed accordingly. So when their request comes in, sorry, I have to look at my cheat sheet here. Don’t mind me. Um, processes are now defined and you have access to continuity of information.
You don’t data silos anymore. And that’s really important because now we understand and could run quick reports. Where’s my, where’s my obligations going? What contracts do I have? Uh, who do I do business with? When do these contracts expire? What commodities am I buying? Um, and being able to run downstream visualization engines to understand where your obligations are going to your third parties is really critical. And it really simplifies that.
If I can get an environment that’s easy to use and up and running quickly, um, and that’s kind of what you do. So you have this kind of form that goes and it’s dynamic from, So someone could say, remember those, choose your own adventure books. Am I just dating myself here? Mm-hmm. So, um, if something happens, you could go ahead and, um, get people to be able to acquire whatever they need and, and this, the system will move to the speed of what they are seeking. I was gonna say, we did a screenshot of Dwayne’s actual approval process here. We made it small so you couldn’t see it.
Duane: But actually kind of to highlight how complex those approvals can actually be and all the people that need to touch on parts of the process in the organization. Yeah, we’ve really appreciated the flexibility within the workflow and realize also that over time roles for workflow can change over time. And not all contracts are created the same. So you can, we can adjust and say, we know certain IT contracts might be subject to different cybersecurity review, or how do you look at what are certain criteria you’re looking at with some of your software partners for AIcapabilities?
And whether that’s exposing your data outside of your walls or not. There could be differences from, uh, you know, finance, finance standpoint. So we, we, let me, let me take one step back. I apologize. So we have the slide up. We’re talking about how procurement’s looking at this to help. Is this vendor we want in our landscape or have in our landscape finance might be looking at this and improving? Does this fit in our strategy? Do we have the capacity to, of the resources and the organization to move it forward? Does it fit in our financial plan? Do we actually have the capital available 2025? You know, the challenges we were talking about earlier, we had some constraints on capital. And any of those would give our finance leader, our CFO, the ability to weigh in and say either yes, no, or not now in that workflow process. But the process gives us the ability to kind of flex up and down on dollar values and criteria that we want those individuals to be aware of and approve on.
Shannon: Great. And go talk a little bit about visibility and being able to see this information.
Duane: So visibility is very significant with renewals, this board is in two pieces. One is renewals and general throughput of a request. So this particular board that we’re looking at here left to right is backlog. What work is coming up, uh, in the queue to be looked at, what contracts are coming up for renewal or where is a request in the process sitting for review and approval. So we can see when something comes in the door, I can see when the different parties have approved it, whether there’s comments in there, uh, before it gets to, hey, it’s been assigned a backlog assigned in progress and closed as the way these particular buckets are set up.
But it, the, the tool gives us the ability to see the throughput from the point of input all the way to output. And in the past, you wouldn’t, we would not have had that type of visibility ‘cause it would have been, how do I know when Sally sent an email over to Bill and how do I know when Bill routed it to this individual within the tool?
This helps us track where it’s at in the process and we’ll get into a little bit of some of the other things. I’m excited about that, uh, a little bit later on. What’s nice is also you have the ability to have internal stakeholders collaborate with you in the environment. And so all those conversations will get captured. Hey, I’m gonna write legal about section 6.2, limitation liability. Could you Okay, with the red lines that I put in, yes, I’m okay with it, or no, I want to change to this. And all these things are captured. So you have continuity, all of a sudden you’re not, you’re not working in data gaps.
And when you have these your audit teams will love this because every, every change is captured. So to start to understand, the process went from John Doe asking for the original request, and then it goes into Dwayne’s organization, starts working that request and it goes into finance or legal or to InfoSec or whoever it is to start. And every time it’s captured or I engage with the supplier, here’s the new version, or I change the dollar amounts of the negotiation. And so when you have this continuity of information across every single different module, right, um, it’s very powerful.
Shannon: Great. I was gonna say, I’ve flipped to another screen that can also show you this information as well in terms of backlog, what you’re working through and some of the communication that you can have both internally and also with suppliers that can be captured.
Duane: Yeah. The piece that we appreciate at Lands’ End, there’s different views for the different audiences and the users that are gonna be in the tool. We haven’t really prepped or talked about this piece, but, um, one thing that we’ve, uh, the tool gives you leadership level.
So some of those backlog, how do we manage all of this at an aggregate level? This gets us into individuals looking at the specific line items and like an IT manager owning a specific contract or service or facilities owning a specific contract, they can go in and see where they’re at and track status all the way through this. Right?
Shannon: And so the scale of this for a team of only three has actually been pretty profound. To date, the volumes, we can kind of walk through these, but there’s a pretty significant amount of transactional volume that we’re putting through a team of three in procurement. And I’m, I’m assuming like many of you in the retail space, your legal team is not, you know, we don’t have people sitting around waiting to pick up requests and contracts for review but we are pushing through about 350 to 450 travel requests a year, 500 to 600 capital and other expense requests a year, 300 to 400 renewal requests a year.
That’s a fairly, that’s a pretty high volume that if you don’t have a tool to try to help you track that and make sure that you are, you know, checking the box and having an audit log, that things were done really hard to manage that you’re not gonna, you’re not gonna do it with three people if you’re still doing everything in spreadsheets. Um, we do have about 4,500 contracts in the system now. We do think that’s nearly all of them.
We still have some, you know, the challenge there is you don’t know what you don’t know, right? So how many contracts are we still potentially sitting out there? But we have a, we do feel pretty good about having that number in there and the ability to create greater consistency, consistency in analytics across those contracts. And I think, again, one thing that’s been interesting when we’ve spoken is that it’s not like this is a one and done, you’re constantly evolving and making changes and doing new things. So I’m curious about the impact that this has overall had on your team.
I would say there are a couple of impacts. So directly to the team, as I mentioned, our team is three. We have been able to reduce the numbers. We are still providing, or we have been able to provide a single source of truth. We’re able to say, here’s all of the contracts that we have today. We’re not reaching out and trying to gather that information, uh, from as many folks across the board as we had in the past. Um, it does give us the ability to report to senior leadership and management much more.
So we have better insights, better data to say here’s what we have coming up, gives us the ability to plan our staffing and our overall pipeline of work much better than what we had in the past. We were very much a reactive fire drill type of, uh, approach with the spreadsheets and the individuals that we had in the past. And it’s getting much more proactive and insightful going forward.
Shannon: So talking about that, what are the plans moving forward?
Duane: Yeah, so from, from a raindrop standpoint, our plans kind of focus on, uh, three things.
One, integrations, uh, two on supplier management and three on AI. So on integrations I mentioned that we have ERP going in, we put in Raindrop in and we have a lot of legacy systems. We didn’t necessarily integrate with a lot of our other solutions that might have other approvals or, uh, I wanna say reporting structures, the things like that. But as we move forward with our new ERP platform, there are gonna be opportunities in the short term to connect to some of those other legacy systems that will stay.
But it’s also gonna be connecting to SAP to figure out how these look at the end-to-end process and figure out how we can connect those together better for a more seamless user experience across the board. So that from the integration standpoint, that’s what we’re looking at from a supplier standpoint, uh, it’s twofold.
I mentioned that we use the tool to gather the information internally for new requests, but once those requests come in, we end up emailing our suppliers today to gather information, whether it’s gathering the contract information for an NDA or DSA or gathering information for, uh, payments and banking info.
All those are still pretty swivel chair today. And we do want to use the tool for that. It can be a collaboration space, not just with internal folks, but with our suppliers as well. And that’s something we wanna expand on in the future.
And then third is, I’m sorry I didn’t cover the second bullet, uh, on suppliers, that we talked about the number of contracts we have in the system, the ability to get those in one place and do greater analytics with it to say where do we have consistent terms and cons, where do we have gaps in some vendors?
Where do we have the ability to consolidate? Uh, that’s, how do you use that data for better decision making? That’s one of our next steps.
And then the third bucket is around AI and how do we use the tool, uh, to help kind of expand on the contract piece, uh, point out trends or best practices in our tool to help with contract generation, to do you wanna flip ahead?
I think we missed the one to help with risk analysis of our vendors, um, think about 2025 and the risk of, um, how tariffs were gonna impact us.We went back through a number of contracts manually.
So you have attorneys and you have procurement people reading contracts to figure out what flexibility we have given the environment that we’re in. You can go out and Google all kinds of other stuff today that would help figure that out. On a personal standpoint, we haven’t had the ability to do that on an enterprise level. If we get all these contracts into that tool, we’re optimistic about how AI can help us with the analysis of contracts. And we’re not, I don’t wanna say dependent on attorneys, we’re always gonna be dependent on attorneys and procurement folks, but it could help alleviate some of that pain.
