Switching from Free to Paid Project Management Tools: What to Consider
- Adilla

- Sep 2
- 7 min read
Updated: 3 days ago

Using free project management software is beneficial for small teams, but it can be frustrating when you encounter a paywall for a tool you want to utilise. Not only that, but as more complex projects come in and the team gets even bigger, a project management free plan might impact the creative workflow.
So, what other factors should a creative consider before investing in creative project management tools?
Table of Contents
Differences Between Free and Paid Project Management Software
Picture this: you want everything centralised, whether it’s keeping track of your team’s tasks, document storage, feedback space or even a visual of your timeline. There’s only one problem: the recommended project management software gives you all of this, but there’s a limitation.
Commonly, this is what you usually get from free software and paid project management software.
Free Software | Paid Software |
Organise, prioritise, and track work | More advanced insights and data on team workload |
Real-time chat, video calls and file sharing with size limits | Bigger-sized storage and more organised channels for communication |
Limited customisation of tasks and channels | More options for customisation with advanced automation |
Limited free users in one account or space | Extra administrative functions and roles for more users in one account |
Limited integrations of mainstream third-party software | More integration with other third-party apps |
Why Small Creative Teams Start with Free Project Management Tools
For early-stage work and small teams, starting with a free tool is good enough. Other than that, there are several reasons why teams start with free recommended project management software before committing or even staying until they’re ready to switch to paid software.
Test on Workflow and Efficiency
It’s a good idea to conduct a test run with your team before committing to a paid creative project management tool. What works for one person may not work for another, so having the opportunity to try out the software with the team’s current creative workflow before making a purchase is essential to avoid wasting resources.
Simple and Easier to Use
Advanced features and modules can overwhelm some users, so basic functionality might actually be better suited for teams that find new technologies or too many options daunting.
Best Free Project Management Tools for Small Teams
When it comes to adopting free project management tools for creatives, here are a few questions you should ask to ensure you find the right fit.
Do you need visual project mapping? | |
How does feedback work in this tool? Does it allow contextual visual feedback? | |
Do you need integration with other tools? | |
Would you need customisable features to match your team’s needs? | |
Do the limited features affect your team's feeling restricted when the project gets bigger and busier? | |
What type of work will still happen outside the tool? |
5 Free Project Management Tools Creative Teams Often Start With
TESSR
What makes TESSR stand out among other creative project management tools is the ‘Review’ feature that enables hands-on contextual review sessions. Creatives are able to highlight frame-by-frame visual files with shapes or hand-draw on the file itself.
TESSR’s free project management plan for creatives is also suitable for small teams that want to have a trial run or run short-term projects. They offer up to five seats and two metrics for their free account. If you are interested in trying it out, we can show a demo on how to use our software!
Monday.com
With workflow automation and customisable options as its key features, catering to and implementing them for a team’s creative workflow with a unique niche won’t be difficult. This recommended creative project management software has an aesthetically pleasing interface, making it an intuitive user experience.
ClickUp
This project management software regularly updates its features and has a dependable support team. Its automation features and adaptable software make it suitable software for growing creative teams.
Hive
Being able to hold multiple projects in one space, Hive is a recommended project management software for teams juggling different projects in one go. With its own automation process, teams won’t have to spend too much time on administrative tasks.
Wrike
Another flexible and customisable project management tool, Wrike, has multiple project templates for creatives who want to get into adopting software without needing to start from scratch.
Cost vs Value: Is It Worth Upgrading to the Paid Version?
For small teams, relying solely on a project management free plan may seem logical. However, as the team expands, the limited functionality of free software and constant account switching could negatively impact performance.
When you invest in paid software, your Return on Investment (ROI) is reflected in the time saved and the reduced stress. This improvement is made possible through features such as automation, streamlined creative workflows, and centralised platforms.
By using an all-in-one software solution, you can minimise the time and stress associated with switching between different platforms or having to refer to multiple software tools.
Reasons to Upgrade to Paid Management Software
When free options start to feel limiting and affect your team's efficiency, it might be the perfect time to consider paid software. Other than that, here are the other signs that it's time for a transition:

Enhanced Security and Regular Updates
Once you onboard more team members into your project and have higher priority stakeholders, security and buggy updates will become an issue in the long run.
When the software is invested in, security and compliance are more likely to be better. Paid versions of certain software receive updates faster, including any potential bugs. This ensures reliability and stability over time when using the app, like preventing crashes or loss of data from said crashes.
Provide Dedicated Customer Support
Unfortunately, free users are rarely given first-seat customer support, even if it is an emergency to have an issue within the software resolved. So, paid users are more likely to receive faster support.
This advantage is predictable, as most companies consider it essential. Moreover, when dealing with complex software that is central to their operations.
Implemented Bigger Storage and Scalability
As your team grows and you plan more projects, needing more space for your software is a given. Plus, to have centralised storage and a space where scalability is possible is good for the long run. Productivity would be better maximised when there’s more space and less time spent on trying to squeeze everyone into limited account software.
Missing Features and Integration
Free software often limits features based on time or usage per user. This limitation can affect your team’s efficiency, leaving no flexibility to reuse certain features repeatedly. Thus, when this limitation becomes an issue, it’s time to invest in better assisting your team.
When Is the Right Time to Upgrade
Too Many Tools
Jumping to different free tools can be overwhelming and disrupt the team's efficiency. So, when other tools exist in one through a paid plan, it’s best to streamline into one software rather than jumping to another.
Scattered Feedback
Feedback can be cluttered when it’s not properly streamlined into one tool. Thus, dragging the whole revision cycle if feedback gets lost in between chat transitions or verbal communication.
Progress Only Exists on Manual Updates
When submitting a task or updating the progress, it is only reflected on the software through manual updates, which can eat up the time for other tasks. Manual administrative tasks can be updated better through automation, which is usually included in paid creative project management software.
What to Consider Before Choosing a Software

Before choosing and committing to certain project management software, consider these questions:
What are the main parts of your team’s creative process that the paid tools can help with?
Is the expected onboarding time long when adopting this new software into your projects and teams?
Is mobile access important for your team?
Which integration would you need in the software?
Will it reduce the team’s mental load and smoothen workflow, or will it be a burden to adopt into their current workflow?
Will your team be able to use it in their daily work?
What happens when your team grows or accepts more projects?
While there are many more questions to consider, these would be the essential points you can start with when choosing software.
How TESSR Approaches Paid Project Management Differently
While we do provide a forever-free plan, we suggest your team invest in our project management software, especially for creatives out there.
TESSR is designed with creatives in mind, recognising that creative projects often require a few stakeholders. Our paid plans are suited for medium- to large-sized teams with long-term projects. With up to fifty seats and one hundred teams, there’s ample space for teams that might grow even bigger in the long run.
If you would like to explore further and see how it fits with your projects and your team, reach out, and we’ll give you a demo.
Key Takeaways
Utilising project management software to its fullest potential through its paid version would benefit you in the long run.
Workload distribution would be better, and more efficient workflows would be implemented.
While it is tempting to only use the free version of the software, consider how efficient and productive your team will be when there’s room for scalability and customisable features that would fit the team better.
Frequently Asked Questions (FAQs)
What are the other benefits of paid project management software?
Paid PM software features generate even more detailed reports and analytics. This can offer insight not only into the progress of the project performance but also identify areas that would need improvement, not just on the overall project but also on your team’s task progression.
Why is centralised project management software better than utilising multiple tools?
With a centralised space for everything, anything related to the project can prevent confusion and miscommunication. When data or information is noted down, you wouldn’t need to update it on other tools or platforms to streamline the information.
Would creatives be able to benefit from project management software?
When it comes to creative team tools, there are a few other features we would have to survey or what we would consider creative project management software. Our TESSR project management tool is created with creatives in mind, so if you’re in the creative industry and would like to utilise PM software but don’t know where to start, try us out!
Author Bio
With a background in Arts English, Adilla has been a casual writer for various hobbies, like parodies of animated shows and plots for board games. She loves to read anything and everything from fantasy stories to articles on tips and tricks. Now an advocate for mental health and effective project management for the creative industry. Currently, Adilla resides in Malaysia and is a creative writer at TESSR. To know more about her, check out her LinkedIn.

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