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Time tracking workflows for different team sizes

Last updated: May 13, 2022

Time tracking for different team sizes

While all time-tracking solutions share a basic aim, there are many different applications on offer in the market. The size of an organization is an important factor in determining the kind of solution you need. In particular, as more individuals are involved in a team, the issue of coordination becomes an ever more important factor, and the levels of trust present on a smaller scale must be replaced with more standardized procedures.

In this article, you’ll learn:

The initial problem facing anyone looking for a time-tracking solution is - where to begin? 

There are seemingly hundreds of applications out there, each quoting an apparently unique combination of features. It would be great if there was a way to cut through the complexity to find the solution that is right for you. 

While picking the right solution is never going to be easy (very few important decisions are!) it is possible to focus your search. In this article, we examine the question through an important lens: how large is your team?

For example, are you a:

  • Freelancer: working solo

  • Small Business: fewer than 50 employees

  • Medium Business: 50-250 employees

  • Enterprise: with more than 250 employees, and multiple locations?

After examining how the approach to time-tracking varies by business size, we’ll be looking at some of the key features you should target when selecting a solution for your firm.

Team size comparison

How different sized teams track time

Time-tracking may appear to be a simple process. It is at heart the same for every size of organization: track hours, assign to a category & client and multiply by an hourly rate to generate a bill.

As a business grows, however, some problems disappear as more team members are available to take on roles, while other problems emerge to replace them. Time-tracking is the same way.

1. Freelancer

What you are doing:
Freelancing work is very often non-scalable, one-to-one type work such as editing a document, designing a logo, or consulting. 

What your challenge is:
You may work with others, but as a sole trader you will be ultimately responsible for every aspect of your business - marketing, sales, billing, not to mention the actual work itself. Your time is therefore scarce!

How you track time:
Since there is only you involved, time-tracking itself is a fairly straightforward process. The aim is ultimately to generate a number of hours for a specific project or project phase, so that you can bill the client.

2. Small business (<50 employees)

What you are doing:
While small businesses do a range of activities, those that track time are very often involved in performing more complex versions of a freelance project (e.g. consulting projects that require a combination of research, management, and client communication).

What your challenge is:
The small business employee is very often as - if not more - time-starved as the freelancer. Since there are multiple actors in the equation, there is the added issue of needing to coordinate tasks.

How you track time:
Time-tracking is still a question of ‘generating the total hours’. The presence of more people means that a higher degree of standardization is required. In addition to tracking at a project level, tasks and tags (e.g. billable) will be needed to ensure the time-tracking data can be recorded and interpreted consistently.

3. Medium business (50-250 employees)

What you are doing:
A larger organization will benefit from scale, hierarchy, and specialization. It is therefore possible to undertake a wider variety of work - both in terms of size and complexity. A law firm - with professional / support staff, and multiple levels of expertise - would be a good example.

What your challenge is:
As an organisation grows, the nature of the coordination challenge changes as the organization sub-divides into multiple teams, each with its own manager. There are therefore two levels of coordination - within teams and between teams.

How you track time:
In addition to tracking billable hours, time-tracking is now likely to be as much a business management tool to monitor how effectively teams are performing. In addition to billability and utilization, non-billable activities such as time-to-respond and onboarding can become important metrics.

4. Enterprise (250+ employees)

What you are doing:
Large enterprises that track time cover a wide range of industries from professional services to construction. Scale means a high level of organizational complexity and a potentially diverse range of staff types and work locations. At this level in particular, time-tracking is as much about calculating pay and tracking attendance, as it is about billing clients.

What your challenge is:
Higher complexity means greater potential for error and (as a result) unfairness, with employees potentially gaming the system to work less or get paid more. Hence security and compliance with regulations tend to be higher concerns.

How you track time:
To ensure a common approach, enterprises will tend to go for maximal standardization (=minimal latitude), meaning a tendency towards automation and mechanization, whether this is through punch cards or GPS-based time-logging.

Specific time-tracking features

Now that we’ve covered how the dynamics of a business change with more or fewer team members, let’s look at the implications for choosing a time-tracking application. Before we dive in, a few points.

Freelancer time tracking features

Time tracking features important to freelancers

In-built invoicing

As a time-starved freelancer, you should look to minimize the number of applications you are using. Some time-tracking solutions will incorporate additional functionality. 

If you bill based on hours, it’s logical to go for a solution that generates ready-to-send invoices for your work. Most invoices will allow a certain level of customization (e.g. pick a style or add a logo), and allow you to send directly and track payment.

Free version

With variable income, your fixed costs have a high impact on profitability. Your combined bill for business support services may form the bulk of your cost base, particularly if you work from home.

Many time-tracking solutions have a free option for organizations below a certain scale, as the ‘big money’ is in large organizations. Take advantage of this. Full functionality may not be available, but you may not require this as a sole trader.

Notifications & Reminders

Since the buck stops with you, any help you can receive is welcome. Rather than hire a personal assistant, AI-based reminders can be a great substitute for tasks that are straightforward but can easily slip through the cracks.

For example, if your time-tracking solution is also your invoicing software, it can send you reminders to send invoices and chase unpaid bills. Some apps also have productivity features that block distractions or remind you to take breaks at optimal intervals.

Personal fit

One advantage of being a sole trader is - no politics. Make the most of this fact. Tastes differ when it comes to applications, and the right solution can be as much about taste as it is about the features. 

If you don’t like a solution, you can change it and keep trying out new ones (there are plenty!).

Small business time tracking features

Time tracking features important to small businesses

Input versatility

While (as noted above) a freelancer only needs to find the right software that works for them personally (see previous point), small businesses need more flexibility as there are multiple individuals involved.

Some employees will not want (or will not need) to track their hours in real-time with a start/stop time-tracker. It’s important to have a standard post-hoc entry timesheet for such individuals, while retaining the option for more precise tracking using a real-time option.

Project management functionality

In addition to invoice functionality (see above), a small business will face coordination issues that are closely related to the activities they are tracking for billing purposes. It’s important that the time-tracking solution does not further complicate the coordination.

Some solutions solve this by offering in-built project management functionality options, with features that support task assignment and common workflows like employee hiring and onboarding. In theory, this is a way to streamline your business by reducing the number of solutions your team has to deal with.

Integrations are key

Some functions are best served by dedicated applications. You may use task management solutions such as Trello and Asana, or applications such as Google Drive (document sharing) Github and JIRA (for developers). 

Rather looking for a time-tracking solution that replaces them, it is important to ensure that your time-tracking software integrates with these systems.

This is obviously the case with a specialized system such as a CRM, which may need to be drawn upon by a time-tracking system (e.g. for invoicing), or to input data (e.g. hours billed this year). Automation software such as Zapier can also be a time-saver for a resource-stretched small business, and checking for integrations here is therefore a must.

Medium business time tracking features

Time tracking features important to medium businesses

Time reporting options

Any time-tracking software will include a dashboard so you can review the state of play, and some kind of export functionality so that you can share the data.

When a business becomes large enough that everyone is no longer on a single floor, or siloes between different departments have begun to develop, a more formal approach to presenting the time tracking data may be needed to ensure that everyone is on the same page.

A good time-tracking solution should enable a manager to generate a range of clear reports for a number of different audiences, from the client (the most basic use) to other stakeholders within the business such as upper management, and even the project team itself.

Flexible rates

A more complex organization will require more complex pricing and billing practices, to reflect the fact that not all projects require the same amount of effort and expertise.

A mature time-tracking solution will support the ability to set rates not only by project, but also by employee type and/or task. It should also enable greater variety of billing metrics, such as weekly, monthly or milestone-based billing, to reflect the variety of preferences of a growing, evolving client base.

Profitability management

Business metrics are key to maintaining visibility in a complex, crowded environment with many departments, teams, and priorities. The number one business metric is profitability (with profit - there is no business).

To enable profit-tracking, a time-tracking solution must, first of all, allow you to enter labor costs (e.g. $ per employee per hour), and for employees to log and enter expenses alongside the relevant time entries.

Second of all, to assist in ensuring profitability, project leaders should be able to manage profitability in real-time by entering budgets (for billable hours and/or expenses) and monitoring progress against them, assisted by automatic alerts when deviations occur or are imminent.

Enterprise time tracking features

Time tracking features important to enterprizes

Automatic time-tracking

While not necessarily important for all large businesses, in the case of a large workforce it may not be feasible to police or check time entries made in a traditional timesheet. 

To ensure fairness and standardization, therefore, employers may use technology to track the work patterns of employees. This could include location-based tracking for mobile employees (using GPS technology) or simpler ‘punch in/punch out’ systems for workers in a single location such as a factory.

An increasing number of solution are appearing that attempt to be more precise, for example by automatically identifying a project that a client is working on based on the document or website. The aim is to save time and avoid error. But a word of caution: overly ambitious attempts to “automate away” human judgment can lead to more errors and wasted time.

System Customization

Time-tracking systems deployed at a major company will likely require a number of bespoke modifications (rather than simple integrations that may suffice for smaller organizations).

This may include an element of personal branding or stylistic changes to the basic system, to accord with company color scheme or based on employee feedback. The software may also require modification to fit a company's specific workflows and policies (for example, rounding, locking and auditing of time entries).

Security and privacy, while important for all firms, may well be subject to more stringent regulations in certain industries. For instance, such companies may require the ability to self-host solutions to protect the privacy of their client’s identity.

Attendance and Payroll

With large workforces, the primary purpose of time-tracking may not be to measure work completed for billability purposes, but to provide a basis for payroll administration.

Some solutions are geared towards this dimension, offering attendance reports, to enable a company to identify work patterns, verify that paid sick days and vacations are within the limits of employee contracts, and so determine fair compensation.

Advanced analytics reports, focusing on capacity & utilization, not only provide a helpful diagnostic layer for profitability analysis, but also make the resourcing and hiring planning process smoother.


We’ve covered a number of lenses through which to make your decision. As stated, there is no rigid matrix of features vs company size, although there is a clear trajectory of evolving needs as the number of individuals involved in the time-tracking process increases.

Having considered the above features from the top-down, considering company size alone, we recommend examining the needs of your time from the bottom-up. Even at companies of similar scale, needs still differ by industry, and so a carefully considered set of criteria is likely to produce the best decision.

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