How to Roll Out Time Tracking Software

(without getting fired!)

Written by Asim Qureshi
By Asim Qureshi, CEO Jibble

Time tracking software can help organizations improve productivity, reduce administrative tasks, ensure the company payroll is done right, as well as out-and-out reduce labor costs, but implementing a time tracking software in an enterprise can be a daunting task, and if you’re the person responsible and it goes wrong, the buck will probably end with you. Yes, you could well lose your job over a botched rollout, we’ve heard of this happening. But we’re here to help. With proper planning and an eye on execution rolling out your software should all be a smooth process.

In this guide I will outline the steps involved in rolling out a time tracking software, timesheet app, or time and attendance software in your company, in a way that not only lets you keep your job, but ensure the rollout is a resounding success.

11 Step Time Tracking Software Roll Out Plan

Executing the rollout of a time tracking software requires coordination and communication on many levels to ensure successful adoption, so both employees and management end up winning. Here are the steps you need to follow to make it happen.

1. Define the purpose and goals

Before implementing any new software in the organization, it is key to define the purpose and goals of the software. This is especially important for time tracking software, which may face resistance from employees who feel it is intrusive or burdensome. By clearly communicating the purpose and benefits of the software, and linking it to the broader organizational goals, employees are more likely to understand and accept its implementation.

To define the purpose and goals of the time tracking software, the first step is to identify the specific problems or challenges the organization is facing that the software can address. For example, if the organization is struggling with accurately tracking employee time for payroll and compliance purposes, an employee time tracker can help improve accuracy and efficiency in this area.

Next, it is important to identify the goals of implementing the software. These goals should be specific, measurable, achievable and have deadlines. Goals can include improving productivity, reducing administrative tasks, improving accuracy and efficiency, increasing transparency, and reducing labor costs. It is important to link these goals to the specific problems the organization is facing, and communicate how the software can help achieve these goals.

2. Make sure you choose the right software

Once you’ve figured out why you need time tracking and what you want to achieve, the next step is choosing the right software. With a variety of timesheet software options available, the selection process can be a bit tricky. Look for software that fits your organization’s specific needs, is user-friendly, customizable, and can seamlessly integrate with other tools through an API. Take Jibble, for example, it’s trusted by big names like Tesla, Harvard University, and Pizza Hut – definitely one of the best time trackers out there!

Understand the features and the limitations of these tools. For example, a time tracking software may have a GPS tracking, but does it have live GPS tracking? It may have employee face recognition attendance, but does it work reliably? Or how easy is it to roll out the employee time tracking chrome extension?

In choosing an enterprise time tracking software you need to conduct research and evaluate multiple options as each organization has different needs. This would involve reading reviews and testimonials, requesting demos and then trials, and consulting with other organizations that have implemented the same software. If the software company is reluctant to give you a decent trial period that is a very bad sign indeed. It not only shows short-term-ism but it also demonstrates a lack of confidence in their product. And, of course, also consider the upfront costs of the software, ongoing costs, support, security, and data hosting.

3. Test the software

You’ve chosen the software, but it is absolutely key to test it thoroughly. Ensure you have enough time and move fast so if you’re not happy you have time to go with your second choice. Start with a small team. Create a test environment that is broadly similar to the live environment, and test the software with a representative group of users.

Testing should involve a variety of scenarios that are specific to your needs, and should include a range of users with different levels of technical proficiency. You’ll be surprised at how many things you’ll think are obvious that others won’t be able to figure out, not because of a lack of intelligence, but just because they’re seeing things from a very different perspective.

During testing, it is important to identify any bugs or issues with the software, and to work with the software vendor to address these issues. It is also important to gather feedback from testers, and to incorporate this feedback into the rollout plan.

4. Get the buy-in from key stakeholders

Getting buy-in from key stakeholders is critical to the success of a rollout in an enterprise company. This includes management, department heads, team leaders, and employees. Each of these players will have different concerns or objections to the implementation of the software, and it is important to address these concerns and communicate the benefits of the software.

To get buy-in from key stakeholders, communicate the purpose and goals of the software clearly and effectively. This can involve creating presentations, holding meetings, and distributing materials that outline the benefits of the software. It is also important to listen to feedback from stakeholders, and address any concerns they may have.

Listen, this is really important and often overlooked – the reality is that if stakeholders don’t want this the rollout to work, they’ll make sure it doesn’t work. For employees, a key message to often get across is increased transparency, which means a fairer organization.

5. Plan the rollout

Once buy-in has been secured from key stakeholders, the next step isn’t to rollout, it’s actually to plan the rollout in detail. Identify who will be using the software, and build a timeline for rollout. And plan the rollout in a way that minimizes disruption to the business operations.

Now, identify the resources required, such as IT support, training, equipment, etc… Also, develop a communication plan that outlines how the rollout will be communicated to employees and how concerns will be addressed. You can hold training sessions, distribute manuals, create a dedicated helpdesk or hotline, and provide support during the rollout.

Also, consider the potential impact on employees, which will involve working with HR to ensure that the implementation does not unfairly impact any particular group of employees, or individual employees, and ensure the software’s implementation respects employee privacy as well as security.

It’s often a good idea to have someone from the software company to dedicate their time to your rollout, perhaps even being there at the location when it’s all happening. Such help can be massive.

6. Provide training

Training is critical to a successful adoption and implementation. All users, including managers and employees, should receive training on how to use the software and any policies or procedures related to its use.

Training should be targeted to the needs of the users, and should be provided in a variety of formats, including in-person training, online training modules, and user guides.

7. Provide support

Before rolling out the time tracking software, ensure your team is well-prepared and supported. Establish clear communication channels for ongoing assistance, like a dedicated support team or resources for self-help. Making sure your team feels supported is crucial for a smooth transition.

8. Rollout the software

Once the testing, training, and support have been completed, finally, it’s time to rollout the software. You should be at least slightly nervous! This is where things can get hairy, but if you’ve planned sufficiently you should be good. You should communicate the rollout to all users and provide them with any necessary information, such as their login details and training materials. Also keep track of the rollout, ensure it is proceeding smoothly and as per the schedule, and address issues that arise are dealt with fast.

Regular meetings or feedback sessions and working with the software vendor to address any issues with the software all make a lot of sense.

9. Monitor and evaluate the software

Monitoring and constant evaluating and re-evaluation of the software is important to ensure its continued success. This involves tracking its usage and adoption, and continuously collecting feedback from users, much of it which can be passed on to the software vendor.

The key thing here is not to take your eye off the ball, because that’s what you’re likely to do when things are going smoothly.

Evaluate the impact of the software on business operations, such as productivity, efficiency, and labor costs. This can involve tracking KPIs related to these areas, and comparing them to pre-implementation levels.

10. Make adjustments where necessary

Based on the feedback, evaluation and that ongoing re-evaluation mentioned earlier, make adjustments and, where possible, insist on improvements to the software vendor. This may involve modifying features, improving the user interface, or providing additional training and support. You may not get it, but at least ask! If you can show the vendor that other users will also benefit from the feature, it’ll be easier to push through. At the same time, you will need to be flexible and willing to make changes to your own procedures, systems or even outcomes. You can do all the planning you want, but nothing will go to plan. At best, you will only be close to it.

11. Celebrate roll out success

Once you’ve rolled it all out successfully, communicate the success to all stakeholders. This reinforces the perceived value of the implementation and software, and promotes its continued use. You’ll always have management attention when needed if they believe it was a success.

Share success stories, conduct surveys to gather feedback, and provide regular updates on the impact on business operations. Be transparent and be prepared to address concerns.

Key Principles for Rolling Out Time Tracking Software

Rolling out a time tracking software in a large company can, as you must have gathered by now, be a complex process, but stick to the key principles, namely:

  • Get buy-in from key stakeholders: Getting buy-in from key stakeholders is critical to the success of a rollout. You need to communicate the purpose and benefits of the software and address any concerns they may have.
  • Provide training and support: Often missed, but absolutely needed. Ensure all users are trained and that ongoing support is provided.
  • Communicate: And do it effectively. Communicate the rollout, the benefits, and changes to all stakeholders. It’s easy to hide issues under the rug, but if you do that, that’s when things can spiral out of control.
  • Monitor and evaluate: Monitor usage and adoption, collect feedback from users to make improvements.
  • Be flexible: As business needs change, try to push for the software to be modified to meet those needs, but also be prepared for change taking time or not happening at all.
  • Consider privacy and security: Implementing time and attendance software can raise concerns around employee privacy and security. It is important to ensure that the software is implemented in a way that respects employee privacy, and that any data collected is secured appropriately.
  • Address potential resistance: If employees resist the implementation, this could crush all the good planning and theory. Address concerns early, communicate the benefits of the software, get as much buy-in as possible. If people want to make the rollout work, it’ll probably happen successfully.


Implementing time tracking software in an enterprise might seem daunting, but with careful planning and execution, it can be a seamless and successful process. Start by defining clear goals, selecting the right software, securing support from key players, and planning the rollout. Thoroughly test the software, ensuring flexibility for changes, and provide comprehensive training and ongoing support. Evaluate the software’s performance, make adjustments as needed, and communicate the benefits to all stakeholders.

This comprehensive approach results in a triple win – improved productivity, efficiency, transparency, accurate payroll or costing, and potentially lower labor costs. Successfully navigating this process can be a game-changer for any organization, making the effort truly worthwhile.