In short
Why enterprise AI underperforms despite better models—because capability isn’t the bottleneck; value depends on context, control, and collaboration, plus execution through people/process/tech.
Guest
Tom Scott, CEO of Wrike (Reich in transcript). Background: leads Wrike’s transformation; previously involved in reestablishing the company as a standalone business; has 20-year company history and is adopting AI internally while scaling it across 20,000+ organizations.
Key claims
AI value fails when workflows are messy, data is scattered, governance is unclear, and teams automate “mediocrity.” Transformation requires shared context, repeatable control (audit trail/governance and cost control), and human-in-the-loop collaboration.
Notable examples
Research use case—shared competitive research projects in Wrike using NCP/API connections to reuse prior artifacts and assign actions/accountability. MCP strategy—customers want open architecture: headless/API exposure, BYO models/agents, or native in-app agents depending on constraints. Execution advice—leaders must be hands-on and understand existing processes before automating; leaders should move fast using Bezos one-way/two-way door framing.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Challenge of Automation
0:00 to 0:20
Explore the pitfalls of automating workflows without understanding existing processes.
“If you are not in the details around what is the existing process, then you could be extremely successful automating your workflow.”
Understanding AI Underperformance
0:35 to 1:14
Discuss why AI fails, emphasizing structure over technology alone.
“Here's an idea most enterprises still haven't accepted.”
Context, Control, and Collaboration
1:14 to 3:08
Tom Scott discusses the importance of context, control, and collaboration for AI value.
“It's context, control, and collaboration.”
Defining Key Terms in AI
3:08 to 4:54
Tom Scott defines context, control, and collaboration in the AI landscape.
“The late majority is what the heck, I'm not ready yet.”
Exploring Collaboration in AI
5:36 to 7:22
Discussion on the role of collaboration in maximizing AI's potential.
“And control also goes to the heart of the cost question, which is how do you control the amount of context that you are supplying it to the models in a way that you're not blowing the economics around it?”
Case Study: Research and Collaboration
7:22 to 11:40
Illustration of a research use case and its implications for collaboration.
“Context, that element is very well understood.”
Strategic Use of Agents in AI
11:40 to 14:00
Discussion on the strategic implications of using various agents in AI tools.
“It's like things that you do more than once or more than one person is doing.”
Customer Needs for Open Architecture
14:00 to 17:20
Learn about the demand for open architecture and API integration in platforms.
“with the same customer and often the same person where the, and I'll tell you the common, the commonality is that everyone wants to see a more open architecture in terms of what you are able to do with a platform.”
Navigating Strategy to Execution
17:20 to 21:40
Explore the challenges of transitioning from strategy formulation to practical execution.
“And then testing with them of where are you in your journey?”
Leading Through Transformation
21:40 to 25:50
Understand the complexities and leadership roles in managing organizational change.
“And then I think you have to look back at what you're doing and literally start subtracting at that point and say, how much of this can I take away?”
Show all 18 chapters
Qualities of a Successful Team Member
25:50 to 28:01
Identify key traits necessary for individuals to thrive in a transforming workplace.
“much that they take on responsibility and could drive experimentation.”
Traits for Future Talent
28:01 to 29:46
Learn about the essential traits of curiosity and resilience in candidates.
“It's like, you could be multiples better depending on...”
The Organization of the Future
29:49 to 33:31
Explore how organizational structures are evolving in response to technology.
“There's tons of people talking about what does the organization of the future look like?”
Navigating Job Market Changes
33:32 to 36:56
Discuss the impacts of AI on jobs and the creation of new roles.
“You mentioned the marketing side, like the blending.”
Unique Use Cases of AI
36:57 to 40:08
Discover various interesting AI applications in organizational settings.
“Yeah, and we could have a totally additional topic on the education side of things, but I completely agree with you.”
Advice for Adapting to AI
40:09 to 42:03
Hear reflections on the importance of moving quickly in an AI-driven world.
“applications within my pre and post sales teams to identify use cases at the customer level.”
Advice on Speed and Decision-Making
42:03 to 43:59
Learn about the importance of moving quickly in decision-making and leadership.
“I think the advice I always have for myself when I look backwards is move faster.”
Exploring Wrike and Leadership Insights
44:00 to 45:02
Discover insights on Wrike's advancements and leadership strategies from Tom.
“It's actually some really cool stuff on the agent side and people being able to actually build agents within Wrike.”
Transcript
Automatic transcript. May contain errors.0:00If you are not in the details around what is the existing process, then you could be extremely successful automating your workflow. And what you may find is that all you really did was automate mediocrity and you didn't get the full outcome of what's there.
0:20Matt Paige:Welcome to the Talking AI Podcast, where we talk AI with both experts in the field and early adopters. I'm your host, Matt Page, and we're here to demystify AI for you so you can get some value from it. Let's talk some AI.
0:35Matt Paige:Here's an idea most enterprises still haven't accepted. Your AI isn't underperforming just because the models aren't good enough. It's underperforming because of how work is structured around it. Messy workflows, scattered data, no clear governance, drop even the best tools on top of that, and it struggles. And piling on more tools can make things worse, not better. And Tom Scott has a rare view of this playing out as the CEO of Reich. He sees how AI is actually landing inside 20 ,000 plus organizations from NVIDIA to Jaguar to Land Rover, all while in reinventing his own 20-year-old company in real time.
1:10Matt Paige:And his case is simple. Capability was never the bottleneck. It's context, control, and collaboration. But Tom, welcome to Talking AI. Hey, thank you for having me. Looking forward to the conversation. Yeah, and I want to jump right into this. The models are better than ever to the point where you have the U.S. government pulling back Fable and then we got a taste of it and it goes away in a day by the time it doesn't go away, but you'll be metered for using it. But the models are better than ever. So why are there still companies struggling to get value from it? And I don't know if it's value, but I feel like it's value outside of like individual silos of people is what I've begun to notice.
1:50I think it's because when you really step back and you think about what is happening here, this is transformation writ large. And transformation is never just about the capability of the technology. It always comes down to the people, the process, and the tech. And the thing that is really unique about the moment that we're all having right now is being experienced by pretty much everyone at the same time. Prior technology waves played out in more of a wave-like fashion where you had the technology adoption curve, where you had the early adopters, you had Main Street, you had the late adopters coming out.
2:38So people have time to be able to absorb the change. Instead, what's happening is we're all collectively having this conversation about the technology, all while our people and processes are trying to catch up at the same time. And that's creating a lot of the friction that you're referring to in terms of how do you create that sort of recurring value that happens at scale and not just within an individual or a team silo.
3:06Matt Paige:Yeah, and we have the early adopters, their heads are spinning with everything going on. The late majority is what the heck, I'm not ready yet. And the laggards are just freaking out, I feel, in a big way. And it's the seminal book, Innovator's Dilemma by Clayton Christensen. It's like, just go back to that. I think so many organizations are facing this right now. But you talk about three different terms around this, context, control, and collaboration. And besides the fact they all start with Cs, why do you think these are such important elements when it comes to enterprises and companies actually starting to get value from AI?
3:43So context control and collaboration is the way we at Rake talk about the value of our platform in the era that we're in right now. And if you step back and you quickly define what those terms mean, I think context is pretty uniformly understood that the more specificity to whatever the topic at hand is, in a pre-AI era or in the current era, the better grounded you are in terms of the decision making around that. And the platform we built here at Wrike was always about gathering context to improve decision making. But I'd say everyone's got a pretty good understanding of context. Control, I think people are beginning to have a similar understanding of.
4:38And control can mean a few things. It's what's the audit trail? What's the governance model for users? whether they are human users or whether they are agent users or whether there's some combination
4:52Matt Paige:of the two. Quick break in the pod. I keep hearing the same pattern with companies I talk to. Pod's helping employees move faster, but in many companies, the business itself hasn't changed. The value is still trapped in isolated chats and experiments. And that execution gap is why forward deployed engineers have become one of AI's most talked about deployment models. Stay in bed with your team instead of advising from the outside. It's also why the FDE model is now central to every client engagement we lead at Hatchworks AI. As an official Anthropic partner, we embed Anthropic certified FDEs to identify high value business problems, build and deploy the solution and put governance and security around it, then transfer the capability back to your team.
5:27Matt Paige:If your cloud rollout is still mostly individual usage, check out how Hatchworks AI FDEs work at hatchworks.com slash cloud dash FDE. You can also find it in the show notes. Now back to the show. And control also goes to the heart of the cost question, which is how do you control the amount of context that you are supplying it to the models in a way that you're not blowing the economics around it? So I think there's a lot of conversation today that's coming into control and some of it's termed governance, but to me, it's all part of this control framework of how do you build infrastructure to be able to do this in a repeatable way.
6:04I think the last one is probably the least understood and that's collaboration. And it's interesting because Reich was founded 20 years ago on the idea of collaboration that you had to build to really unlock the human potential. You have to be able to collaborate. like massive exchange ideas, align on them, track progress. And when you come into a world where you are introducing all other types of users into this, and you start with the premise that there is a role for a human to it, collaboration becomes more important than ever. But I don't think we're yet at the point where that is broadly understood in the market of just how important that collaboration aspect is going to be.
7:00And it's the human in the loop collaboration. It's the insight. It's the creative process that is part of that collaboration. But to me, it's hard to really have a holistic discussion on value without framing it up under those three Cs. Yeah, it's several rabbit holes I want to get down off of this.
7:21Matt Paige:I think you hit it right. Context, that element is very well understood. But I still feel like there's this element where, yes, the models are great at taking in lots of context, synthesizing it, pattern matching, doing all of these amazing things. And it's frankly mind blowing blowing in terms of what it can do. But there is this element of shared context, having existing processes and procedures and the models being able to do those things in a repeatable way. And we have things happening like skills. We have agents that do things in a repeatable way. Magentic loops is the new hot thing that everybody's talking about.
7:59Matt Paige:But how do you think about, and whether this is you specifically at Wrike or within the clients you serve, how do you think of going from that element of individual, I'm getting lots of value from this, to entire teams are not only getting value, but it's in a consistent nature, if that makes sense. It does. And I'll give a, I'll give a simple example for a use case that, that I work with. I think it actually illustrates it. It illustrates it well. Like one of the, one of the use cases, I think practically everyone has used a model for is some form of research, right? So whether you are researching to prep for a podcast or you're a family researching for your summer vacation or you're me and you're doing competitive research on what others are doing in the marketplace, it is an extremely powerful use case.
9:04but it is often an individual endeavor where you are delving into this and you can create skills, you can create a specific project around it, but ultimately you are creating some form of artifact that is not easy to collaborate on or share with others other than the form of a final document or tax threat. So that is well understood by anyone who works in a model. And you can understand how you could create a great deal of inefficiency by multiple people spinning up the same versions of a similar research project. What I will often do is when I am doing research of that nature, I will often connect it up via our NCP connection.
9:58So take NCP is just a form of being able to connect multiple types of systems into a model, but using your APIs. And in our case, I will connect up the models that I use into my instance of write, where as I create research, I will extract the key areas. And I'll use that to track both context and collaboration with my senior team. So let's say I'm digging into a thread on competitive features in my space or a go-to-market move that I'm seeing in the marketplace. I can use this to set up a structure within Rake where I've got a project, I've got the shared research, which is that context. And then I'm actually assigning actions and accountability on that basis where we're able to look at it.
10:51When I then come and pick up a future use case as a follow on, I can instruct the model to go back in there and look at that prior project or task that I've set up, use that to inject into the context window rather than spinning up all this all over again as a research thread. That's a really good example of how I see a way to tie some of these pieces together. And that's, it's a very different conversations with customers on the types of workflows that they are utilizing. But that is a common example that I use when talking to them as a way to take something they understand both at the work management level, as well as at the model level and say, look, here's a way to make this more powerful for you to be able to get value.
11:40Yeah.
11:40Matt Paige:It's like things that you do more than once or more than one person is doing. Those are great opportunities for figuring out, okay, how can we automate this? and not do the same thing over and over again, like you mentioned the research task. That's an artifact that should exist and should be referenceable in a way. But I'm curious, you mentioned MCP. Curious your take here, because I've experienced this personally, where I'm a consumer using different products, and every product now has their version of AI or agent or co-pilot or something like this, right? And from my standpoint, it's, man, do I really want to use 30 different agents across 30 different products?
12:21Matt Paige:Or do I want to essentially bring my own agent, kind of like BYOD back in the day, where I can bring my own agent to the party? And the way of doing that is via MCP. But I'm curious, how do you think about this strategically? Because there's value on both fronts, where there's agents that are native in the platform itself and users are interacting with those. There's obvious value of being able to connect via MCP so users, agents can reference the system of record. I feel like there's this third pillar of almost agents that are geared towards interacting with other people's agents versus humans necessarily.
12:57Matt Paige:They're basically making the experience stupid simple for somebody else's AI to interact with that system of record. This is all very nebulous and moving very fast, but just curious how you think this is playing out strategically and maybe where you think it's going to land in the future. Yeah, this is a really good example of something where I had a going in point of view that has been challenged in conversations that I've had with our customers. My going in point of view was that there would be a cleaner segmentation of how customers thought about that question that you just posed, which is, is it a bring your own model discussion?
13:47Is it a use the agent inside the existing application? Is it the, we just want to keep using the application as it is today? And I find that sometimes, in fact, frequently I'm having all three of those conversations with the same customer and often the same person where the, and I'll tell you the common, the commonality is that everyone wants to see a more open architecture in terms of what you are able to do with a platform. And some companies are referring to this as a headless model, but whatever you want to define it as, it's how do you expose more and more of the attributes of your platform through API is a way to expose tools for that MCP context.
14:46Correct? Yeah. That is a common thread on practically every customer I talk to is that there is a great deal of interest there. And that is something that we are investing in our platform to continue extending that capability. The next part is I do think there are a lot of customers that are going to want to bring their own model and bring their own agents. And they require that in terms of working with that architecture that I was just describing. And that's a function of the fact that a, a lot of the bigger customers have relationships with model providers where they've got tokens that they've already purchased or broader, broader tool sets that they are trying to build out.
15:44And we're going to work with them and enable that. The other point though is you can still create a better experience inside the application for some use cases. And the reason for that, think of it as creating a more custom harness for what you are doing inside RIC or whatever your SaaS application is. And on some use cases that are just very core to the workflows or the use cases that you are supporting, I expect that you are going to see those agents be better suited for some of those use cases. And that is where we're spending our time as well. And by working, we're still going to be leveraging those same tools that I was talking about in terms of opening up from an API standpoint, because we'll be calling on that same thing.
16:44It's just, we will be customizing it more within our platform to be able to be able to deliver that value. And so I see this as something that we've talked about for a while publicly and it's that you got to meet the customers where they are. And I've got what I want to build. And then I've got to match this up with some of the constraints that are out there. The way we test this is my senior leadership team and I really prioritize getting in the room with customers whenever we can, telling that three C's story, because that makes a lot of sense. And then testing with them of where are you in your journey?
17:25What are you trying to maximize as an organization so we can understand where do we need to be as an organization to remain valuable to our customers?
17:36Matt Paige:Yeah, I just saw a post you did on LinkedIn a few days ago. So you were just traveling for 12 days, literally doing what you were just talking about, visiting customers across Europe. But I thought it was interesting. The hard part isn't the strategy, it's the execution. So in talking to those customers, I think this is valuable for the audience because I think a lot of people are feeling this. What do you think is, I think, causing that gap, but I think more importantly, how are those that are successful traversing that gap from strategy to execution, like the people that are doing it well, is there anything, any attributes about them, any things that they're doing to go from strategy to actually making something real?
18:19I think one of the key success factors that I've seen and I have experienced is the notion of being hands-on. And I've written about this. I've talked a lot about this, both internally and externally and externally to write. It's that because so much of this is new and because so much of successful process change is in the details. I feel that where I see success in translating strategy to like execution, it's when you have leaders that are right in it with their teams and are able to demonstrate that sort of credibility and authenticity of what they are trying to do. And it's because Because it's really easy to say, hey, I read on X yesterday that this particular company is getting 100x for what they're doing.
19:24Can you make this happen for me tomorrow? Versus having the credibility to say, I built this thing over the weekend. It's really interesting. Can you explain to me why we can't do this on a broader scale? Those are two very, very different conversations. And the answer may still be, can't do it. Let me explain to you why. But getting in there and really feeling where those tensions are comes out. And I'd say the other area where this really comes out is when you get into the details around process. Because if you go back to what we were talking about at the very beginning, transformation is always accurate around three things, which is people, process, and tech.
20:07And if you are not in the details around what is the existing process, then you could be extremely successful automating your workflow. And what you may find is that all you really did was automate mediocrity. And you didn't get the full outcome of what's there. And so again, that really requires you to get in and understand what are we doing? What does it look like for simple purposes? What does it look like on a piece of paper? And where does it flow? Who decides where is the value added step? And then at that level, you can say, we can take the big ideas and turn them into a repeatable play.
20:49Matt Paige:Yeah, I think to that point you mentioned, and folks need to be wary of this because, yes, you can map out the existing process. And yes, you can figure out, OK, let's automate these pieces with AI. But should you even still be doing it that way in this new era? That's the biggest question that a lot of people are missing because you have this, you have intelligence. It's like literally intelligence that you have at your disposal. And people should really think, do we just rethink this, whatever process you're looking at holistically? I think your going in position has to be, we're not going to do that, that we are going to completely blow up the way we were doing things before.
21:29And that doesn't necessarily have to be your first step. I think your first step is to understand what are we doing today? What are we trying to achieve? are we being bold enough in our thinking? And then I think you have to look back at what you're doing and literally start subtracting at that point and say, how much of this can I take away? Not because these people were not doing a good job or at one point it didn't make, it made sense. But I do think you have to start by subtracting as much as possible as part of that. And then you can start to holistically think about what's the system design of what you were trying to build What's the minimum number of pieces that's unique there?
22:10Matt Paige:Yeah. And you're at a rare vantage point because you're not just advising clients on this. You're going through your own reinvention story, I would imagine, as a company because you've been around for 20 years. I'm curious, what does this look like for you internally as a company going through this transformation? Because there's the people side of it. There's the product side of it as well. And you're you talk about process earlier. In a lot of ways, Wrike is a process focused product and company in a sense, right? And it was very much deterministic. And then you have this probabilistic tool that comes into the mix.
22:46Matt Paige:And I'm probably throwing way too many questions out of you, but what's that been like for you leading through this transformation? Because again, like a lot of our listeners are going through this exact thing right now. I'd say like transformation is messy. no matter how you want to frame it. And transformation has to be owned by the CEO. I don't know that there is an exception to that. So when you go back and you ask about transformation here, I've been with Rike for four and a half years and I've been CEO for three years tomorrow. So four and a half years, you came in at the beginning of 2020.
23:35Matt Paige:So you were right when everything just completely changed. So I would say I have led multiple transformations here. I led a transformation when I came in the door with the founder, because I didn't come in as CEO. And I led a transformation with the founder right when I came in the door to reestablish right as a standalone business. I led a transformation when I took over the CEO spot from our founder three years ago. And I'm in the middle of leading a transformation right now as we adopt into a new era. And I think there are a few attributes that I always look to on this. And one is personal accountability.
24:24So I was making the point that the CEO has to lead it. And I've always tried to lead this business with that accountability in mind, that you have to make the call and you often have to make the call alone. But you still owe a lot of answers on why and how you made it. Because you need people to have confidence in the thought process and the willingness to follow you. My comment on hands-on plays into that as well. I am not the technical founder of Reich, but that is not an excuse of where I should be spending my time. It's just a fact. And that means that I need to demonstrate the use of technology and how it is advancing, because that is a way for me to help lead the company through this change.
25:23It's also a way for me to recruit the next generation of changemakers. So if you think about, you've got to be able to state the why change, and then you've got to demonstrate the fortitude as a leader that you're going to take them through it. And you've got to expand that capability. But as you start going through this transformation, you find out that there are all sorts of friction points. You have people that rise to the occasion and really surprise you in terms of just how much that they take on responsibility and could drive experimentation. And you get surprised the other way as well, where you have people that had been really strong contributors or even leaders for the business that just aren't ready for the moment that's in front of you.
26:14You get all of that through those transformations that I was talking about. I'd say we are in the middle of it right now. We, last year, we kicked off what I referred to as a series of sprints to help advance some of the transformation in this area. And the reason I called them that was both to simplify the number of things that we were trying to do and also put a flashlight on it. We've created employee groups across all of our teams where we're pushing experimentation. And as we see progress, we look to scale it and communicate it and roll it out further. But that's that hard part that I was talking about of taking the strategy and then turning it into execution down at the function and team level to actually generate that change to the organization.
27:09Matt Paige:Yeah. And I think what you said in the beginning, folks need to listen to you. Transformation is always messy. It's just inherently always messy. And the end of the story is never clear until you're at the end of the story. Right. So I think anybody that is feeling these pains in their organization, like maybe they're having to pull people along or maybe maybe you're getting pulled and you don't like it. I mean, it's just it's the natural way of change. I think what is it the saying goes that the two two things people hate the most is change in the way things are like it's just like there's this natural tension that always exists.
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27:45Matt Paige:our nature. But you talked about people a little bit. I'm curious, what is your ideal persona of a person that works at Rikley? What's that person? Because I think it's totally different than what it was before. The person that's amazing in today's world, it's not like, oh, I'm a 10X engineer. It's like, you could be multiples better depending on... But what traits qualities do you look for? I look for curiosity, first and foremost. So whether I'm interviewing a relatively young new entrant, or whether I'm interviewing a candidate for a senior level executive job here, I'm looking for someone who is deeply curious.
28:35Because you can't train that. That's something that just has to be innate in the person that you're bringing in. And touching back on what we were discussing a few minutes ago about transformation being messy, I'm also looking for resilience. Because change is never linear up and to the right. It's often very cyclical. And I need to have someone who's curious, able to retool, and take a few lumps along the way. because you are going to have to absorb some losses.
29:10Matt Paige:Yeah, and I posted something the other day. It's like kids are going to grow up today thinking it's just totally normal that intelligence is at their fingertips and AI just does things for them. And I think who's the most naturally curious group? It is young people. I am so high on this next generation coming in. They're facing, I think, a ton of turmoil in terms of finding jobs and things like that. But I think they are going to be just so powerful and dynamic because they're having to navigate this and they're going to be the ones that are using and leveraging AI the most at their fingertips.
29:45Matt Paige:I love that. Resilient and curious as the two things there. What about the org of the future? There's tons of people talking about what does the organization of the future look like? You have Jack Dorsey on one side. I think it's pretty compelling. I don't know if you've saw his thing around from hierarchy to intelligence and talking about organizations have always been structured to disseminate information down and then get it back up. And that's why you had middle management. You have Y Combinator talking about their AI native organization and all of these different elements to it and token maxing it, all these terms that keep emerging.
30:20Matt Paige:But any thoughts on where that org of the future is going to land? I think if you go back to what essentially the post-World War II org structure has been for companies, exactly like what you described. It was increasing specialization at every level of the organization designed to move information up and down the hierarchy. And that model is being completely contested today by what you can reasonably learn. And a good example would be in areas that were outside my subject matter expertise, it used to take me a significant amount of time to get up the curve on something new. That's no longer the case.
31:21I can walk into a session with a subject matter expert today and be completely briefed on the background of it. It doesn't make me an expert, but it makes me educated enough to have an in-depth conversation and be able to make a decision there. If you think about what this means for the org itself, going back to that curious point that we were talking about, it means we need to be looking for full-stock employees. And what full-stock employees means is that they have to be able to orchestrate more of the work around them because the reporting and communication, we can build more automation on that basis, but we need to have someone who's got a broader span.
32:10And you saw this first, like you typically see within engineering disciplines. where you went from this idea that you had this somewhat linear SDLC, software development lifecycle, where you've got the development phase, you've got a front-end engineer, you've got a back-end engineer, you've got QA, all these pieces working in a somewhat linear fashion. And we're moving very rapidly towards more of a full stack, and you refer to it as a 10x or 100x engineer, that's a full stack professional that's sitting there. They may not be a full expert in every aspect of that, but they are able to deliver that full stack.
32:52You're going to see the same thing in marketing. And marketing is classically divided the same way where you've got content marketers, you've got brand marketers, you've got performance marketing. Ultimately, you're going to get to more of a full stack model where they are orchestrating this work around. And it is like one basic theme that you're bringing to market that sits under the overarching view of brand, but you're not overly specializing in each one of these segments to be able to deliver it. And so I think orgs are getting exploded as a result. And I think you are starting to move around to move to this forum where you've got a lot fewer people that need to sit in the middle ranks and you've got a whole lot more people that need to take on that full stack, that full stack view of value creation.
33:48Matt Paige:Yeah, it's such a good point. We see this on our teams. You mentioned the marketing side, like the blending. It's not just blending, but it's like the crossover of roles. And you see this on product and engineering and things like that, to where a product person can take something a lot further than they ever were capable of before. and on the flip side, so can an engineer, so can a designer. So there's this interesting mix that's starting to happen. It's funny. I just saw this. I don't know if you saw this study. Let me see if I can actually successfully share my screen, but this was by Ramp and they're basically looking at AI's impact on jobs.
34:24Matt Paige:And there's a lot of narrative on AI taking jobs, which I think AI is going to impact a ton of jobs, but they looked at this split by those that are high AI intensity, they call it, versus low AI intensity. So organizations that are adopting AI at a higher rate, and they're actually growing headcount, which I thought was an interesting phenomenon. And I think there will be displacing of jobs, but I think new roles and jobs will emerge that we never experienced before, just like every other transformation before as well. Any thoughts on this impact? I don't know, anything you've seen personally or in the job market with clients, things like that, on that impact, either at an aggregate level or maybe at a lower level?
35:12So I do have a few thoughts on this. I think one, it is fairly undisputed that you will see job impacts based on this type of technology. Whenever there is a transformative impact from a technology standpoint, there is a jobs impact. I'll pair this, though, with the other part of my outlook, which is I am firmly a humanist in the view that humans do evolve and that they evolve to create new roles and find space for themselves. And so from that standpoint, I'm firmly in that camp and I believe that I am building technology that enables humans from that standpoint. And so while there absolutely will be a disruption, I spend a whole lot more of my time worried about how we are going to create these full stack professionals more than I worry that we've got a jobs apocalypse in front of us.
36:25But I very much spend a lot of time thinking about there are not very many full stack people that are out there today. And the ones that are there can name their price as they well should. And we as leaders of companies and technology and even education need to think about how we are going to better equip the younger generation to be able to not just take the technology, but invest in the curiosity and the resilience to be able to deliver what I think these jobs in the future are going to be.
37:03Matt Paige:Yeah, and we could have a totally additional topic on the education side of things, but I completely agree with you. It's leaning into the curiosity, that human nature that we have. And I think at the end of the day, humans are always progressing, looking for more. It's just in our nature, right? It's the expansion of aspect of humans in a sense. But I'm curious, so like what's a few more things, but you're obviously using AI a lot. Any weird use cases of AI, any things that you just could not imagine your life without, whether that's specific agents, specific use cases, leveraging AI, any interesting use cases personally?
37:44It could be at work. I don't know if I'd put it into the interesting or unique, but I'm happy to share a lot of the things that I do. So first, given my role, I'm not deeply embedded in a lot of recurring workflows. A lot more of my work is ad hoc and bespoke. But one of the interesting issues you often run across in my position is you talk to a lot of smart people and a lot of smart people put written documents in front of you or positions or just a view of what we need to be doing as an organization. And historically, it could be very challenging to figure out where are the points of alignment that you need to focus on across an executive team.
38:39Because if everyone shows up and we're all talking about 70 % of the same thing, it's not always obvious where the conflict is. And I have used models that help really brighten the lines between positions as I'm trying to create alignment in the organization. And I use that to drive discussion with my executive team. So that's one use case. As I was talking about earlier, I'll often do that work at the model level. And then I will drive that down into our work delivery platform and say, look, here, here's the areas that we need to be discussing on. Here's where I need your opinion. Here's what we're going to, we're going to do to move forward.
39:23The other area that has been enormously useful is just the to-do management of execution, where you have a million conversations over the course of the day or a week. and collecting all the follow-ups. So when it gets into right for work execution, it's great, but not every interaction I have happens there. It happens across a number of different surface areas. And I'll use that technology to essentially sweep all of that together across my email, across Slack, across Wrike, and then make sure that gets organized into a work delivery mechanism where I can ultimately hold people accountable. Now, other use cases that I've seen across the organization that I'm not the creator on, but I'm really excited about is we've done everything from build up specific customer applications within my pre and post sales teams to identify use cases at the customer level.
40:31That always gets me really excited. I've got some early stage work that we've done to essentially take customer support tickets and automate maintenance fixes as they come in, where you've essentially got a completely connected pipeline of a ticket, comes in, gets assigned to a task, gets assigned to an agent, gets assigned to a review, gets sent to production. That has an enormous amount of promise for us as an organization. And I've seen a lot of interesting use cases that gather information across multiple systems to automate decision making, whether it is sales plays that have worked or whether it is just trending at certain types of customers to be able to drive focus on that within the region.
41:20So we're doing a lot of experiments at the team level. As I mentioned earlier, we'll scale it up whenever we see something else that's a promise behind it.
41:29Matt Paige:Yeah, that's interesting. You mentioned the one around the leadership team earlier. We did one at one point where we fed in everybody's disk score, their personality assessment. And it helps you interact with that person or how you should interact with them or based on what they're sending. It kind of gives you this level of insight that maybe you haven't considered or whatnot. But maybe last question here. What advice would you give your pre-AI self, which probably right before you joined, right before everything seemed to have changed with generative AI. What advice would you give yourself as an operator?
42:07I think the advice I always have for myself when I look backwards is move faster. You think you're moving quickly on things and you look back and you're like, I do. I should have moved significantly faster on that. That's guidance I give to my team. as guidance that I give to myself is that given the pace that everything is moving at, your going in assumption has to be that you're going too slow. And that's definitely the advice that I would give to my younger self.
42:42Matt Paige:It's the saying, if the jury's out, the decision's already in or something along those lines. One more question for you on that same notion. it's the and i think that advice is true over time but i feel like it's even more so true now because you can do things much faster which can be a good thing or a bad thing right but you can make bets and do things at a higher velocity than you could before thanks to ai um i'm curious any nuance there that you've seen, or maybe that's a good thing or a bad thing. I still think probably the best framework to look at this is Jeff Bezos always talked about the one-way door, two-way door.
43:30Matt Paige:Totally, yeah. And I can't think of a better way to frame it. And if it's a two-way door, I don't think you can move fast enough on things. And obviously, if it's a one-way, I should end up owning a lot of the one-way doors and making that call for the organization and being clear on where it is. But that is the framework that I think works best in that situation. The joys of being a leader. So, Tom, where can people learn more about Wrike, all the things y 'all are doing? It's actually some really cool stuff on the agent side and people being able to actually build agents within Wrike. It's pretty cool stuff.
44:10Matt Paige:But where can they learn more about you? in Reich? Yeah, so there are a few places that I would flag. We maintain a lot of active discussions on our website, so www.reik.com. The other place is I'm very active on LinkedIn with a number of posts and articles that are out there. I write in a number of publications. Those will also get posted on my LinkedIn feed or Reich's feed. So I would encourage you to check out both of those along with a number of my leaders that are also posting on some similar topics. Yeah, highly recommend checking out Tom on LinkedIn. I was just before the episode going through some of your posts.
44:50Matt Paige:There's tons of great insight there for leaders or anybody just going through everything we're going through with today's transformation. But Tom, thank you for jumping on and talking AI. Thanks so much for having me today. Thanks for listening to the Talking AI Podcast. If you enjoyed the show, give us a follow or subscribe on your favorite podcast platform. And don't forget to leave us a review. We love those. For more info on Talking AI, visit TalkingAIPodcast.com. Quick break in the pod. If you're listening to this podcast, chances are you've been thinking about how to actually use AI inside your business.
45:26Matt Paige:And that's exactly why we built the AI Opportunity Finder. It's a free tool that helps you uncover high impact, tailored AI use cases based on your business, your goals, your pain points, and your industry. No fluff, no generic use cases, just real ideas that fit your business and they're ranked by ROI potential. It takes about three minutes to run and it's like having your own personal AI strategist for free. If you want to try it for free, check out the link in the show notes or go to hatchworks.com backslash AI dash opportunity dash finder.
From the publisher
The models have never been better — so why do so many companies still struggle to turn AI into real, repeatable value? The answer, Tom Scott argues, isn’t the technology. It’s everything around it: messy workflows, scattered data, no clear governance. Drop even the best tool on top of that and it struggles, and piling on more tools can make things worse, not better. Capability was never the bottleneck.
In this episode of Talking AI, Matt Paige sits down with Tom Scott, CEO of Wrike — the intelligent work management platform used by 20,000+ organizations, from NVIDIA to Jaguar Land Rover. Scott came up through finance and operations, including a stint as CFO at Zebra Technologies, so his lens is the operator’s, not the evangelist’s. He’s now steering a 20-year-old SaaS company through its own AI reinvention while watching thousands of customers attempt the same thing.
The conversation covers Wrike’s three-part framework — context, control, and collaboration — why context, not capability, is the real bottleneck, and why the collaboration piece is the most underrated of the three. From there it moves into the strategy-to-execution gap, the case for hands-on leadership, the “bring your own agent” question reshaping SaaS, the full-stack professional replacing the specialist, and the honest, messy reality of leading transformation from the top.
In this episode, you’ll hear about:
- Why capability was never the AI bottleneck — and what actually is
- Why everyone is experiencing this technology wave at the same time, unlike prior ones
- Context, control, and collaboration — the three Cs behind Wrike’s value
- Why collaboration is the least understood and most important of the three
- Connecting your own models to a system of record via MCP to kill duplicated research
- The “bring your own agent” shift and what it means for SaaS platforms
- Why hands-on leaders — not top-down mandates — close the strategy-to-execution gap
- The risk of automating mediocrity instead of rethinking the process
- Why transformation is messy and has to be owned by the CEO
- Hiring for curiosity and resilience over deep single-domain expertise
- The full-stack professional and the collapse of the middle of the org chart
- A humanist take on AI’s job impact — and why we lack full-stack people
- How Tom personally uses AI to align his executive team and sweep up follow-ups
- The advice he’d give his pre-AI self: move faster, and the one-way/two-way door test
Key Moments
- 00:01:19 — Why value stays trapped in silos: it’s people, process, and tech, all at once
- 00:03:19 — Defining the three Cs — context, control, and collaboration
- 00:06:21 — From individual wins to consistent, repeatable value across a team
- 00:07:26 — A research use case: connecting your model to Wrike via MCP
- 00:11:09 — Do you really want 30 agents across 30 tools, or bring your own?
- 00:12:50 — The open, “headless” architecture customers actually want
- 00:17:32 — The hard part isn’t strategy — it’s execution
- 00:18:17 — Hands-on leadership: “I built this over the weekend…”
- 00:21:00 — Don’t just automate mediocrity — rethink the process first
- 00:23:20 — Transformation is messy and has to be owned by the CEO
- 00:29:06 — The ideal hire: curiosity first, then resilience
- 00:31:31 — The org of the future and the rise of the full-stack professional
- 00:36:38 — A humanist read on AI’s job impact
- 00:39:31 — How Tom personally uses AI to drive alignment and execution
- 00:44:21 — Advice to his pre-AI self: move faster
- 00:45:38 — The one-way vs. two-way door decision test
Key Links
Mentioned in this episode:
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