This conversation breaks down why so many AI and automation investments fail inside organizations, and what to do instead. The core idea: companies keep layering new tools on top of processes they don't actually understand end to end, which leads to wasted spend, poor workforce planning, and avoidable layoffs.
You'll learn how to audit the technology you already own, measure usage on a much faster cadence, and redesign work so that systems support people rather than create friction. The discussion also covers how HR can lead enterprise-wide transformation, why human judgment still matters most, and how to get started with AI without fear, even if you're later in your career.
Key Takeaways
- Most AI failures come from adding automation on top of processes no one fully understands.
- Layoffs are often evidence of poor planning rooted in misreading how disruptive technology will be.
- Start by maximizing the tech you already bought before purchasing anything new.
- Measure tool usage monthly or weekly, not on 12 to 36 month contract cycles.
- Employees often work outside the system because the tool creates friction instead of leverage.
- For every dollar spent on technology, organizations may spend seven to eight on wraparound work.
- High performers with AI are far more likely to fully rearchitect processes, not just bolt AI on.
- Workflows are usually built for clean cases, while real work is mostly edge cases and exceptions.
- Psychological safety is essential, or people hide how they actually get work done.
- Don't fear AI; block short, regular time to experiment and you can multiply your impact.
Timestamps
0:36 Meet the guest and Vendi
0:57 A career across HR and tech
1:45 Layoffs and their real root causes
3:53 Why AI investments keep failing
8:08 Optionality instead of working around tools
9:00 ROI versus compliance spending
13:07 McKinsey study on rearchitecting processes
14:20 How Vendi works and the 30 day sprint
19:00 Protecting PII and sensitive data
22:37 One wish: start with AI, drop the fear
Connect with Dave Foley
https://www.linkedin.com/in/davefoley1
Thanks for listening to The Courageous Choice. Be sure to leave us a review and subscribe so you don't miss any conversations.
For more information, visit
Powered by the WRKdefined Podcast Network.
[00:00:05] Welcome to The Courageous Choice, a podcast about what it really takes to lead at the edge of change. Because here's the truth, strategy isn't enough anymore. The world of work is moving faster than ever, and the leaders who stand out aren't the ones with all the answers. They're the ones willing to make bold decisions in moments of uncertainty. This podcast is about those moments, about those leaders, and because leadership today isn't about certainty, it's about courage. The courage to see differently, act decisively, and step forward anyway.
[00:00:36] I'm Jamie Jacobs. Welcome to this episode of The Courageous Choice. I'm honored today to be here with my friend Dave Foley. He's the founder and CEO of Vendi, and I also get to partner with him at GigTalent. Welcome. Thank you so much for being here. Thank you for having me. I have been wanting to tell your story since we met last year. So can you share a little bit about your background and what led to Vendi?
[00:00:57] I've been in HR and HR technology my whole career. So first decade, I started as a practitioner. I led talent acquisition for the Americas for Gartner. I worked for Korn Ferry and basically was evolving the passive candidate recruiting process early on before LinkedIn.
[00:01:14] I spent seven years at LinkedIn, and then the last seven years I've been in HR tech. So I've been in the industry my whole career, and it's been sort of this confluence of technology and HR, and obviously the moment that we're in right now is perfectly suited for my background. I'm excited. I actually think this is really cool that the people today leveraging our experience that gave us unique lenses and then applying it to today, right?
[00:01:38] And like nobody's better positioned to have come up with what you did at Vendi. Can you share a little bit about what your vision is? We've all noticed all of the layoffs that kept coming up. And personally, I just was affected by that friend's really close connections and wanted to try to figure out what is the root cause or what are some of the root causes for the layoffs that we were seeing.
[00:01:59] And so one of the fundamental issues that I found was that when we think about work, we're not necessarily looking at how technology, especially as we design work, how technology is going to disrupt that design. So what I was seeing was organizations hiring only within two to three to four months, letting people go. And to me, that was just classic evidence of poor planning. But the poor planning was grounded in technology and our misunderstanding or lack of understanding of how disruptive that tech was going to be.
[00:02:29] So I decided, how do I get my arms around it and help organizations kind of look around the corner to understand what's coming? And Wayne Gretzky used to always say, you got to skate towards the puck is going. And from my standpoint, when we think about building work and designing work, we have to look at where technology is going to understand how do we design work for both today and the near future. So that was sort of the foundation. So one of the things that I think we kind of make assumptions, we've talked about it from an HR perspective.
[00:02:58] There's a thing called organizational network analysis, ONA. And that was a big aha for many organizations to understand how work gets done within the people architecture, right? It doesn't necessarily happen in kind of the org structure or design. You know, it's who's the connectors, how does data flow? And so we've learned a lot in that. And some people still don't know what that is, right? So I think that there's sometimes we make assumptions and we all know what that can lead to.
[00:03:22] And the same is true on the tech side, which is only getting more and more complex as there's new technologies evolving. Everyone's kind of trying to solve gaps. But I love what Vendi does because it really helps organizations understand how work is happening right now, how the tools are happening, being utilized or not. Every organization I go into, there's always low-hanging fruit around underutilization of functionality within existing tools.
[00:03:46] Can you talk a little bit about, like, how Vendi works and why you wanted to do it? So first of all, we've all heard the sort of MIT studies of all the failures happening in AI investments. And really one of the root causes there, too, is the fact that, you know, businesses are trying to add AI or automation on top of processes that they may not know how they run end-to-end. Assumptions.
[00:04:12] And they're based on assumptions and misunderstandings or standard operating procedures and training manuals, right? So when we thought about the building Vendi, we wanted to first look at, one, you know, what is the obvious low-hanging fruit? And the obvious low-hanging fruit is you have invested six, seven, eight figures in your technology sack. So our focus exclusively is today on HR technology.
[00:04:37] We believe there's a huge transformation movement, there's a big black box in HR, and there's an opportunity to connect HR processes with the outcomes that businesses need most. So from that standpoint, we wanted to look at, okay, well, within your existing tech investments, are we fully utilizing the technology we have, number one? And then, number two, almost every vendor is on this journey to do all things to all customers, right? And so there's becoming this greater and greater overlapping set of capabilities.
[00:05:06] And so Vendi wanted to make sure we could look at, hey, what is the possibility within your existing stack today? But also, where is that stack going so that we can make sure we're getting the very most out of what you've already invested in? But it's gone further than that. So it first started out with, how do we get a better ROI from our HR technology? And then it morphed into something bigger, which is, are we actually seeing the outcomes that the business needs most? And do we actually have that designed well?
[00:05:33] And what's unique about the moment that we're in is technology is, we've historically had to work around technology, right? Technology has been sort of structured and rigid, and we've had to train around the capabilities of technology. But what's shifting is, now technology is coming to be more tailored to the needs of the people and the outcomes of the business. So that shift required us to look at processes differently, look at technology and investments differently. And that was one of the fundamental beginnings of the product.
[00:06:02] But ultimately, you have a board and a CEO basically mandating investment and change using AI. And yet, you can't really do that unless you understand how the work gets done today. So essentially, if you're investing in these areas and you don't know how the work is getting done, you're basically just scaling the wrong thing. Solving the wrong problem. And solving the wrong problems. Yeah. I literally see this every day. When companies are implementing new systems, you're dealing with multiple things, right?
[00:06:28] People's aptitude for change, both as the user, maybe the functional expert, but also, like, if it's an HR tech, you know, if the rest of the organization didn't want to lean into self-serve because they're so used to people doing things, you'd end up with a form instead of using the workflow in the tool, right? There's this aptitude for change. But there's all these reasons why tools were implemented the way that they were, right? And designed and all of those things.
[00:06:54] And so there's this potential underutilization just of, like, how it was when you first started. Sure. For whatever reason. Maybe you didn't have the people to do it. Maybe people didn't want the change, whatever it was. And then, like you said, it's dynamic, right? I mean, those tools have all of it. They all have roadmaps. They're adding additional functionality. It's really amazing. And you may or may not know and integrate that into workflows and process and SOPs and things like that. So it's like it's dynamic.
[00:07:23] And so even it's going to be probably outdated today. Yeah. Today, technology, as we all know, is moving at such a pace that in a month that capability set might be completely different. Or that organization that is your strategic partner that you're about to sign a contract with may not have the funding in 6 to 12 months to deliver against their roadmap that you're counting on. Lastly, you know, you might have the ability with agentic tech to be able to build your own capability.
[00:07:50] So the build versus buy conversation actually becomes a much more prevalent and important conversation to be had within an organization. Like that idea of so if you understand what you're actually trying to solve for. Yeah. Now there's so many ideas of how to solve for it. Yeah. I like to use the term optionality, right? So like we were always stuck with our technology and we try to work around it.
[00:08:16] Now what we need to understand is what do we have that we can get the most return from immediately? And we also then have to measure it on a much more frequent cadence. So instead of once a year for those contracts or even once a quarter, literally once a month, once a week, we need to be listening to our people and understanding how they're utilizing the systems because they themselves are experimenting with new capabilities. Whether it's within your stack or outside of your stack.
[00:08:42] And so, I mean, one of the biggest themes that we found in all of our conversations with, you know, end users and CHROs is that, you know, a lot of your employees are actually working outside of the process. Because guess what? The system is creating more friction than it's creating more leverage. So you have to ask yourself, we're spending all this money on this tech. Are we actually getting an ROI on it or are we doing it for mainly compliance reasons?
[00:09:06] And I think that's where the sort of talent lens comes in because when we think about technology and not just in the HR stack, we need to make sure like are we leverage, is the technology enabling the right human judgment at the right time for the right outcomes? And who gets to decide and design that? Unfortunately, most of the orchestrators and consulting firms in the world today look through mostly a technology lens and they want to optimize again for cost, for efficiency, for margin, and all of that's important.
[00:09:34] But what they're not necessarily considering is how important the human is. And if we don't know what the human is doing, how can we quantify the value there? You're a human? Yeah, I'm a human. Oh, wow. I guess me too. I want to enable the human as much as possible. And that's just sort of a missing link.
[00:09:51] And then the last point I'll make is I believe that the CHRO and HR should have a really important role in helping organizations drive this transformation because they have a unique set of skills in organizational design, development, change management that most of these technologists don't have. And you're beginning to see a lot of this boomerang of organizations laying off only to hire back because they realized that the talent they laid off was incredibly valuable.
[00:10:17] As organizations that have for so many years been talking about engagement scores and retention, they're really quickly eroding that confidence in kind of the employee-employer contract. Yeah. And it's being redefined, which is why we're seeing so many people choose to work differently. Almost 50% of the workforce is now involved in the gig economy in some way. Yeah. And, you know, I am just such an optimist. I have loved working in great organizations.
[00:10:44] And I think that, you know, that's kind of the challenge to organizations right now is to have that talent lens, that human lens, to really think about who are you as an organization. That doesn't mean you don't optimize. That doesn't mean that there might not be layoffs. It just means how you do it matters. Yeah. And being strategic through that. So the workflow related to comp required managers to input data for the annual comp process.
[00:11:11] And this organization hadn't given visibility at that level to compensation decisions. And so, you know, they just decided not to do it, which that might be an appropriate decision. You know, we could argue that or not. But it's not about right or wrong. If you have like a report from Vendy that shows that as an example, then that can be – it can resurface the discussion around is it still – do we still feel so strongly that we don't want to leverage a tool for this because we don't want to educate, for example, our managers in that role.
[00:11:41] Of compensation management. Yeah. Yeah. You also have to listen to your people and you have to understand how they're utilizing the tech that you've invested in. And so from that standpoint, psychological safety is also a major component to this conversation. I think a lot of people are reluctant to share the work that they're doing or how they're leveraging technology and maybe even hiding at work for fear of their job being eliminated.
[00:12:03] When in fact, you know, what's unique about what we're doing is we want to understand how is the system supporting the outcomes you're trying to achieve? Is it actually, again, helping or getting in the way? And what are you doing differently to actually get your job done most effectively? If we're coming from that lens to understand how do we help you do your job better and, oh, can we change the technology to better support you?
[00:12:26] It's a very different conversation than saying, you know, we're going to look for different technology to automate the process or do something differently, the shiny object. And that inherent fear only gets worse. So we want to fundamentally solve how do we better enable people with tech? Yeah. Or just in general, because even surfacing like the other use case that you had shared was around somebody still, but like a manual form that people were using. And people were embarrassed that they were still using the tool or this form and like so old school.
[00:12:55] But for whatever reason, they didn't adopt it. They didn't make the change when it was at implementation and they've just stuck with it. Right. And so being able to like ask the question, does that still make sense? Like they might get a different answer today. McKinsey just came out with a study. They looked across 31 dimensions for AI EBIT. And they found that high performing organizations with proper AI investments are three times more likely to have completely rearchitected their processes.
[00:13:24] So that's a fundamentally different world than, oh, we want to invest in AI and just slap it on top of what we're already doing. Yeah, write a job description or whatever. We need to look at how the tools are being used. We have to make sure we're enabling our people in the right way. And then from there, we can look at what are the different combinations of people in tech to achieve the outcomes we want to achieve. So we never want to say, hey, you should be buying this new tool. You should be buying this new capability. It first starts with what do you already have today? And what can we redeploy based on the capabilities of the tools that you've already invested in?
[00:13:54] And it's not just looking once. It's looking literally like on a weekly or monthly basis, depending upon the cadence that the client needs to figure out how quickly is that tech going to move? And can we then evolve according to that roadmap? I know you have clients that are on like monthly, quarterly kind of recurring process. So they get, help me understand, they get like a report that shows like either variance or opportunity or how does that? How we get started is we meet the customer where they are.
[00:14:23] So we, you know, every organization has some degree of documentation. We don't need any sophisticated integrations or APIs to get the information directly from their system. We just need standard operating procedures, SOP docs, org charts, job descriptions, any kind of usage or telemetry data. And from there, we can understand how a system has been implemented. The second half of it is we've mapped out all 12,000 human capital management vendors, and we understand the capabilities of every vendor in the landscape.
[00:14:52] So it's kind of like piecing together what we know versus what we know is possible. And our journey is to essentially get to as strong of an understanding of how work is getting done in the context of your technology stack. We then basically map out the work and identify where do we lack insight or where do we have additional highly contextualized questions. We engage with the subject matter experts.
[00:15:15] We let them know, and by the way, we engage via both an interview and a follow-up questionnaire using our UI to understand what are they doing differently and why. And from there, we get to a point where we get to a map of what that work ultimately looks like in that digitized form. You may have heard the term digital twin. We get to that sort of digital twin output. And so what we're trying to find is in 30 days, where do we get started?
[00:15:39] One of the biggest challenges with AI in the world today is everyone's trying to sort of over-architect this transformation. Really, what it comes down to is what is that first step you can take today, tomorrow? What's the one or two things you can do immediately within your existing environment to see an immediate ROI and then scale from there? So we offer a 30-day sprint. We ask our clients to share their materials with us. We map out their workflows. We interview several of their top subject matter experts. And we come with some immediate recommendations. And then we grow from there.
[00:16:09] But at that point, once they're embedded, there's a cadence where every month we're looking at their systems. We're looking at their stack. We're hearing from their people. And we're looking at better combinations. And effectively, that led leads to do we maintain our technology investments? Do we look at other tools that are in the market? Do we build? Do we buy? Those are the conversations we're looking to enable. That's really exciting. I mean, knowing where you're starting, being intentional, defining the outcomes. And then the outcome goals will continue to shift.
[00:16:39] And so does the utilization and functionality and options within both the landscape of technology options and obviously their existing stack. And then there's a whole – so back to the ecosystem. So then if you look at the ecosystem, the human loop becomes incredibly invaluable at this stage as well. So, you know, obviously working within the gig ecosystem, we have these entrepreneurs who have decades of experience.
[00:17:03] Wouldn't it be more valuable to you if, let's say, you are – you have a workday shop or an Oracle shop and you want to look at your technology and look for opportunities for innovation to have someone who's actually done the same type of implementation at another organization and can bring all of that knowledge, all of the mistakes they made? You know, they pitched the CFO and they realized all of the bruises from the things that they got wrong. Wouldn't you want to have that context and knowledge as we consider your options?
[00:17:31] So, again, it's about optionality here. And so we look at marrying both the diagnostic and the data we generate with the people who have done the work to be able to deliver the confidence that our clients are essentially looking for. And we're dealing with HR. It's very sensitive. And it's in a world where we want to also enable the HR leader to own the transformation itself. So one of the other things around the gig ecosystem we talk about is cross-functional transformation.
[00:17:58] And from my standpoint and from Vendy's standpoint, what that means is how do we enable the HR leader with technology to not just transform their own HR stack but then become a catalyst to transform their other functional leaders within the business? So our vision essentially is to better prop up or enable HR with data to be able to do this across the enterprise. That's the thing. Like data informed decisions, data.
[00:18:25] And, you know, I've seen it happen where HR leaders are starting within their own function. Like organizations where there's a mandate, you know, within your own function, go get X savings or do whatever. And so they can start there. And then they can leverage that and the learnings around change management and internal comms and work redesign and things like that kind of across the broader organization. You know, to your point about, like, security, I can imagine I've already had questions.
[00:18:50] People are like, okay, this is, you know, PII, highly confidential information. Like, obviously you've thought about that. But how do you answer that question? Yeah, yeah. So we redact data locally before it even comes to us. We do another redaction. So before we expose any data to, and we have our own proprietary tech stack. But before we expose any data in an LLM, we make sure that it is completely sanitized of PII or PHI depending upon the situation. Thank you.
[00:19:20] I think it takes courage. This is the courageous choice. So it takes courage to make the leap that you've done and go all in. Can you just talk a little bit about the journey and what that's felt like for you? I feel like I'm at a moment in my life, call it a second mountain moment, where I'm devoting the rest of my life and career to helping people. And I saw so much pain from the layoffs that we're living in. I see so much fear about what's happening in AI and automation.
[00:19:45] And if we can create greater clarity for organizations to hire and design work more effectively, we're going to be less likely to let people go because we were blindsided by a new model or a new tool or a new technology. When we look at technology, we look down the horizon of the roadmap. We measure the capability of a tool or a vendor across multiple different dimensions.
[00:20:14] Things like their financial health. Things like revenue per employee. Things like, of course, their roadmap. Because we want to make sure that that business is now a partner of yours. They're no longer a vendor that's going to sit there and serve the same technology over the next three years. They're going to be iterating very rapidly. So from that standpoint, we want to do the investor-grade due diligence that any organization needs to feel confident in their partners. I love that. Well, an HR tech founder with a people heart.
[00:20:44] Yeah. For me, it just comes down to if we can provide greater clarity, organizations are going to be smarter about hiring and managing that workforce. There's a whole L&D play where we can then start to see where the skills and the capabilities are needed in the future. So if you're looking at work and you can start to figure out where is work bottlenecking today? Yeah. And typically, by the way- Where is adoption happening or not? Where do we need, explicitly need the right type of human judgment? And I used to use the term sort of air traffic control.
[00:21:12] Are we delegating work at the right place in the right time in a process to the right people? And do we actually have all of those nuances understood and built in? What I've seen is most workflows are built for sort of blue skies, clean sailing day-to-day, but the edge cases, the exceptions are not necessarily taken into consideration. We're humans. And almost everything I've ever seen in my career has been an edge case and an exception.
[00:21:37] So if everything is an exception, then what you're ending up doing is you're doing most of your work outside of the process, outside of the system, on Slack, in one-off emails, in one-off meetings. And if you can quantify that cost to a business, it's massive.
[00:21:53] And so one of the stats that I heard is that for every dollar an organization spends on technology, they're spending $7 to $8 on wraparound services and work that the system was designed to do but just can't do because it's not designed well. So unfortunately, a lot of organizations like to blame the people, lay off the people, when in fact it's the process and the system that's inherently flawed.
[00:22:19] And so we want to get to the root cause, which is how do we get to clarity around how work gets done and how do we make sure the system serves the people and supports the people and looks around the corner, not just looks at what's available today. That's right. If you had one kind of wish for our listeners today, what would it be? I would say everyone, you know, don't be afraid of AI. I would say this is the same advice I would give to an organization. It's find a way to get started.
[00:22:45] So if you're thinking about it, I'm not going to give you sort of the basics, get on and download, you know, Claude and do X, Y, and Z. But I'll say, hey, block 30 minutes a day, two, three days a week, and just start experimenting. Start trying to use the technology. And you'll find that you're going to be completely surprised by what's possible. The other thing that I'm really excited about is the fact that there are folks who are not really tech forward and grow up with technology.
[00:23:14] And they may be the individuals that are most nervous about what's coming. But they're the people the world needs the most. So particularly if you're later in your career, I'd say don't back away, lean in. Spend that time. Because actually, if you can get just that two or three percentage point leverage from the capabilities of technology, you can 10x anything you've ever done in your career. So I think it's just an incredible opportunity.
[00:23:41] But fear is guiding and driving a lot of us. That's my wish is to eradicate fear. So thank you so much for joining us today. I really appreciate it. Thank you all for listening. And we'll see you on the next episode. Thank you for listening to The Courageous Choice. If you enjoyed this episode, please leave a five-star review to help get the word out about the podcast. And don't forget to subscribe so you don't miss out on any of our future conversations.
[00:24:11] If you'd like to know more about gig talent, please visit gigtalentagency.com or email us at podcast at gigtalentagency.com. See you in the next episode.


