Strategic Gap Analysis in Action: ClickUp's $5.8M Opportunity

In this post, I'll talk about ClickUp's public roadmap. I'm going to review it to perform a strategic gap analysis. My goal is to see if their roadmap is aligned with their strategy and to show how a company can find a potential opportunity by being more strategically aligned.

Clickup's vision and strategy

First, let's quickly talk about what ClickUp is. It's a productivity tool, similar to Notion or monday.com, and their vision is to be "the everything app for work." In my opinion, that’s a bit of a broad goal, but I understand that condensing a whole vision into one line is difficult.

To get a better sense of their direction, I've looked at their website and other posts and have pulled out what I think are their three main strategic goals:

• Eliminate App Sprawl: ClickUp aims to embed AI directly into its platform—tasks, docs, projects, and whiteboards—so teams don't have to constantly switch between tools. This is a very sensible goal, as it keeps all the work in context and reduces the need for repeating information.

• Productivity and Efficiency: A primary goal for these types of tools is to reduce busy work and free up time for high-impact tasks. ClickUp does this through automation, contextual intelligence, and workflow streamlining.

• Enhance Collaboration and Communication: All collaboration tools need to excel at creating a connected environment, especially for teams that aren't in the same physical location. ClickUp has recently introduced new features like Chat and Whiteboards that are integrated directly into the workflow to minimize context switching.

Disclaimers (Just So We're Clear)

Before I get into my analysis, I want to say a few things:

• Thank you to ClickUp for having a public roadmap. This is a brave move that brings a ton of visibility and understanding.

• This is not a complete analysis. I don't have access to their full roadmap or strategy, just what is publicly available.

• I also don’t have an understanding of their commercial or go-to-market strategy, which is a key part of how companies grow.

• This is an exercise to demonstrate a common problem that exists in many companies out there and help you understand how to review your own roadmap and become more strategically aligned.

ClickUp's Public Roadmap: Let's Get Into It

I've taken the publicly available roadmap and analyzed it in a spreadsheet. I was happy to see that ClickUp has a lot of information, including two different versions of their roadmap: a high-level one and a more detailed view with upvoting from the community. I used the high-level roadmap to guide my analysis.

What I found is that there are some great, strategic features in their plan that will have a high impact:

• Work Schedules and Team Hubs: I think these features are important because they create a central identity for teams, making it more difficult to replace ClickUp.

• Connected Brain, Connected Search, and AI: If done right, this could be a major differentiator and a very strategic feature for them.

• MS Importer: This is a key feature for driving growth. It will help people migrate from Microsoft Teams, which makes it easier for new companies to adopt ClickUp.

• Sync-up Recordings: I think this is a great feature for asynchronous productivity that helps ClickUp compete with tools like Zoom and Slack.

However, I also noticed a trend: many items on the roadmap are related to UI/UX redesigns and feature reworks (e.g., calendar, table view, chat cards). This could be a red flag. It may indicate a high level of maintenance work and technical debt, which can distract from building new features and driving growth.

What I Think Is Working

• Strong Alignment: I found a strong alignment between their roadmap and their strategies. This is a great sign.

• Transparency: ClickUp is very transparent, not just with their roadmap but also on their YouTube channel, where they talk about the product's direction.

• Healthy Balance: There is a good balance between highly-voted community requests and features with fewer votes that are likely more strategic.

What I Think Could Be Improved

• Broad Vision: The vision and strategies are a bit too broad, which risks diluting their focus. Having a more refined vision behind the scenes could help the teams prioritize better.

• Focus on Retention Over Growth: The roadmap seems to be heavily focused on enhancing existing workflows and pleasing existing customers rather than attracting new ones. There are very few features that target new user acquisition.

• High Maintenance: A significant portion of the roadmap is dedicated to UI/UX reworks and fixes, which could indicate a high level of technical debt. This takes time and resources away from growth initiatives.

• AI for AI's Sake: I think there’s a risk of AI overreach. Adding AI to everything just to keep up with the trend, instead of focusing on solving high-impact problems, can create a lot of noise.

Strategic Alignment & Potential ROI

I've calculated the strategic alignment of ClickUp's public roadmap.

• Strategic Initiatives: 50%

• Supporting Work: 17.5%

• Maintenance Work: 32.5%

The maintenance work is higher than you'd expect, which is a bit of a concern for a product that isn't that old.

But even with a 50% strategic alignment, there's a huge opportunity. Based on an estimated R&D team of 300 people and an annual cost of $130,000 per employee, and a target strategic alignment of 65%, ClickUp could be looking at a potential reinvestment of over $5.8 million per year.

This isn't about hiring new people; it's about reallocating the same resources to more strategic initiatives. You could be funding two to three entirely new initiatives per year without having to hire a single new person.

Final Recommendations

• Refine the Vision: While "the everything app" is a great tagline, a more refined product vision could help teams prioritize and find those new growth opportunities.

• Address Maintenance: The high amount of rework indicates that they should be paying more attention to technical debt and usability issues.

• Focus on Growth: The roadmap feels more like a maintenance roadmap than a growth roadmap. ClickUp has a great product and a huge user base, but they need to find a new push for where they want to go next.

This is a critical moment for ClickUp. They've either achieved their vision or are very close, and the question now is where they put their efforts next. They are playing a very clever game, but a little more strategic focus could unlock massive potential.

This kind of strategic focus isn't a happy accident; it's the result of having a clear framework to align your team's work with your strategic goals.

Do you want to drive change and improve your team's strategic alignment?

Ready to stop building features and start building business impact? Join my webinar, Are You Building Features... or Business Impact? to learn how to measure and fix your strategic misalignment.

You can find a video version of this strategic gap analysis here: