Summarize this article for me pleaseFrom the Desert to the Desk: Work Sprawl Is Universal
Not long ago, I found myself in Saudi Arabia, meeting with leaders at the country’s first EV manufacturer and the world’s largest sovereign wealth fund. These organizations are building things on a scale that’s hard to fathom—$20 billion ski resorts, cube-shaped cities the size of twelve Empire State Buildings. It’s wild, and it’s inspiring.
But what struck me most wasn’t the scale of their projects—it was the scale of their challenges. No matter where you are in the world, Work Sprawl is the silent force holding teams back. Whether you’re building a futuristic city or running a sales team in the U.S., the symptoms are the same: too many apps, processes, and context slipping away between them.
It’s incredible to see ClickUp doing its thing in a completely different part of the world, but the reality is that Work Sprawl is everywhere.
Solving Work Sprawl: ClickUp’s GVP of Commercial Sales on AI and the Future of Work
- From the Desert to the Desk: Work Sprawl Is Universal
- Naming the Problem: What Is Work Sprawl?
- My First Battle with Work Sprawl: The Snowflake Years
- The Modern Sales Stack: When Every Minute Counts
- The Hidden Cost of Work Sprawl from a Customer Perspective: Symptoms vs. Root Cause
- Overcoming Overwhelm: The Power of a North Star
- The Matrix: A Blueprint for AI Transformation
- The Cultural Revolution: Building a 10x Team
- Overcoming Resistance: The Role of Peer Champions
- Real-World Results: From Frustration to Flow
- Conclusion: The Time to Act Is Now
Summarize this article for me pleaseNaming the Problem: What Is Work Sprawl?
Work Sprawl is the fragmentation of apps, processes, context, and now AI, in the workplace across disconnected systems—an increasingly common challenge for modern teams. It’s the hidden tax on productivity, innovation, and engagement. We estimate it costs over $2.5 trillion globally in lost productivity. But the real cost is harder to measure: the frustration, fatigue, and sense that work is harder than it should be.
The insidious part of Work Sprawl is that it rarely announces itself. Most people don’t call it by name—they just feel the symptoms: delays, frustration, chaos. It takes forever to get things done. People are frustrated. There’s a general sense of fatigue and delay. But underneath it all, the root cause is always the same: disconnected tools, inconsistent processes, missing context.
Summarize this article for me pleaseMy First Battle with Work Sprawl: The Snowflake Years
I first encountered Work Sprawl at Snowflake.
Our sales ops team was scoping all kinds of projects—localized pricing, new workflows, you name it. But every project was managed in Wrike, while dependencies lived in Salesforce, and the dev team tracked their work in Jira. There was no two-way sync. Every week, we’d meet to check if priorities were aligned. It was excruciating.
That resulted in tremendous frustration across teams, interpersonal conflict, and a calendar full of meetings that solved nothing. Everyone was pulling in different directions.
The tech was supposed to help us move faster, but it actually slowed us down. I remember the pain of sitting in those meetings, knowing the lack of integration was costing us not just time but morale.
Summarize this article for me pleaseThe Modern Sales Stack: When Every Minute Counts
Running a sales team today means living in a heavy tech stack: Outreach, Salesforce, ZoomInfo, Clari, LinkedIn Sales Navigator—the list goes on. Reps bounce between tools just to get a single email out. And in sales, time is literally money. If it takes ten minutes to send an email instead of two, you’re losing real dollars.
Whenever a new tool or feature is introduced or someone wants to buy or pull something in, my first instinct is to ask where and how we can do this within our current systems. I don’t want to add something else unless it’s absolutely necessary.
Can—and should—all of this live in a single pane of glass? The better question: what would it take to make that possible?
The truth? Every new tool adds more noise—more “ghost work,” more blind spots, and more complexity to juggle. The job is already complicated—every team has processes they need sales to follow. So, the simpler we can make the job, the better.
Summarize this article for me pleaseThe Hidden Cost of Work Sprawl from a Customer Perspective: Symptoms vs. Root Cause
Most customers don’t walk in saying, “We’re drowning in Work Sprawl.” What they describe are the symptoms: “Work feels chaotic.” “It takes forever to get things done.” “People are frustrated.” The root illness is always Work Sprawl, but it’s hard to name because it wears so many faces.
When I talk to executives, I ask: If you could go back five or eight years, would you design your systems the same way? Everyone has the same epiphany: No, I wouldn’t do it this way again.
They realize that a more thoughtful approach to information silos, data transfer, and collaboration would have saved them years of friction. But most organizations have let their systems sprawl organically, with every team picking their own tools—whiteboards, project management tools, and more— and little to no executive intervention.
And now, as they look to build their AI tech stack, they’re faced with a choice: repeat the mistakes of the past, or take a more strategic, unified approach. The answer is always clear—be thoughtful, be intentional, and don’t let Work Sprawl happen again.
As AI in the workplace becomes the norm, the absence of a unified workspace and live context is starting to limit its actual impact. AI is only as good as the context it can access. If your data is scattered across 18 tools, something we call Context Sprawl, you won’t see the compounding benefits AI can offer.
Summarize this article for me pleaseOvercoming Overwhelm: The Power of a North Star
So how do you start to fix Work Sprawl, especially when the problem feels overwhelming? For me, it’s all about having a North Star.
Context is that North Star.
The power of AI is only realized when it has full context. But getting there isn’t easy, especially if you’re entrenched in a mess of systems. In fact, as we’ve seen in countless real-world transformations, overcoming Work Sprawl requires bold but incremental steps—choosing one workflow at a time, consolidating it, and building momentum toward true Convergence.
I’ve learned that you have to take it one piece at a time, but be definitive and bold about that piece.
For example, take project management. “Just move everything over” sounds simple—until you hit scattered docs and half-built plans. Whether you go in phases or flip the switch, the real work is boldly carrying context forward and wiring it into the system. Half-steps strand knowledge; bold ones give AI the whole picture.
I often share our internal story about moving to ClickUp Chat from Slack. Everybody was dragging their feet. We failed the first time, trying to move over one team at a time. It just didn’t work. Then, as soon as we were bold and decisive, announcing in no uncertain terms that on a particular day, Slack would be discontinued and everyone would move to ClickUp Chat, it actually happened! Slack was gone, everyone moved, and it was great. Now, we have magical AI experiences in ClickUp Chat that we didn’t have otherwise.
I get it, the inertia of the status quo is strong. But the future of work demands a bold, intentional plan. But as leaders, we need to recognize that it’s the lack of top-down guidance that created Work Sprawl in the first place.
Summarize this article for me pleaseThe Matrix: A Blueprint for AI Transformation
There’s a framework I use—a kind of matrix for AI transformation. It’s not about chasing shiny objects or adding more tools. It’s about:
- Unifying your workspace: Fragmented data is AI’s kryptonite. Bring your work into one place—a true Converged AI Workspace
- Prioritizing context: AI needs context to deliver value. Connect your data, processes, and conversations
- Empowering operational champions: Find the people in your org who think in systems—give them a platform to drive change
- Bold, top-down leadership: Set the vision, make the call, and communicate the “why” relentlessly
- Bottom-up support: Change is a team sport. Empower your teams to experiment, build, and share what works
- Iterate and scale: Start small, measure impact, and scale what works
When AI is layered on top of fragmented, siloed data, it’s like asking a chef to cook a meal with ingredients scattered across 18 kitchens. But when you unify your workspace and context—a true Converged AI Workspace—AI can finally deliver on its promise: surfacing insights, automating tasks, and freeing up your team to focus on what matters. This is why solving Work Sprawl with AI isn’t just about efficiency—it’s about unlocking entirely new ways of working.
The ClickUp difference: AI that actually works for you
When I talk to teams about AI, the biggest challenge isn’t enthusiasm; it’s execution. Everyone wants smarter tools. But without access to real context—what your team is working on, what’s already been discussed, what needs to happen next—most AI ends up feeling disconnected and underwhelming.
That’s where ClickUp Brain comes in. Because it lives inside your workspace, it actually understands what’s going on. It pulls from your tasks, docs, chats, and goals to deliver answers that are grounded in reality—not guesses.
And it’s flexible. You can switch between leading AI models—like ChatGPT, Claude, Gemini, and more—depending on what you need in the moment. Fast draft? Smart summary? Deeper reasoning? You’ve got options, without ever leaving your flow.
Then there’s ClickUp Brain MAX, a desktop AI companion, which takes it even further. You can talk, and it listens—literally. With the help of its Talk to Text feature, you can say what’s on your mind and turn it into an update, a task, a doc—whatever you need. It’s context-aware, always-on, and gets smarter the more you use it.
It’s not just AI for AI’s sake. It’s AI that actually makes your work better.
Summarize this article for me pleaseThe Cultural Revolution: Building a 10x Team
The future of work isn’t just about better tools—it’s about a new mindset. I believe the future is one where humans manage humans, and individual contributors manage agents. That’s how you 10x a workforce.
But you can’t get there with technology alone. It’s a cultural revolution. At ClickUp, we dedicate an hour every Friday for our sellers to build AI. That’s an absurd concept: taking sellers off the floor, off revenue-generating activities, to build AI. But it’s the only way to empower every person to automate 30-40% of their job and free up time for what matters.
That is a cultural revolution. The companies and leaders who do that will see their companies grow 10x and win.
IT alone cannot drive this. Only end users know the details of their work. The companies that win will empower every employee to think like a founder, building their own workflows and agents and driving innovation from the ground up.
Summarize this article for me pleaseOvercoming Resistance: The Role of Peer Champions
Change is hard. I’ll go back to the example of moving from Slack to ClickUp Chat. Yes, there was resistance—people wanted their custom emojis and familiar interface. Only when we made a definitive, company-wide move did it stick. And a lot of credit goes to the people who vocally and enthusiastically spearheaded this change.
You have to find the people in your company who naturally think in systems and give them a platform to help move your company along. Empowering operational champions was key. They became advocates, helping their peers adapt and thrive in the new environment. Change management isn’t just a top-down directive; it’s a movement that needs both leadership and grassroots support.
Summarize this article for me pleaseReal-World Results: From Frustration to Flow
Since making these changes, I’ve seen the transformation firsthand. Meetings that used to be about alignment are now about action. AI surfaces insights before I even ask. Reps spend less time bouncing between tools and more time selling. The frustration is replaced by flow.
And our customers? Those who embrace this approach see the same results. It’s not easy, unwinding years of Work Sprawl never is. But with a clear North Star, bold leadership, and a willingness to invest in culture, it’s possible.
And the numbers back it up. According to a Forrester Total Economic Impact™ study, teams using ClickUp saw 384% ROI and saved 92,400 hours by year 3.
Summarize this article for me pleaseConclusion: The Time to Act Is Now
Work Sprawl is modern work’s biggest problem. But it’s not inevitable. With a unified workspace, context-rich systems, and AI-powered workflows, teams can reclaim time, boost productivity with AI, unlock innovation, and build workplaces that work for everyone.
I recommend starting with reflection: Where does Work Sprawl show up in your organization? What’s one bold move you can make this quarter to unify context and empower your team?
The future belongs to those who solve Work Sprawl—one platform, one AI hub, one cultural shift at a time.
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