The Best Leave Management Software for Your Startup

Looking for the best leave management software to use for your startup? You’re in the right place.

We know startups. We’ve been involved in a lot of them. That’s how we know how administrative tasks like leave management can be a drain on productivity.

If you want to get more done, you’ll want to automate PTO requests and leave tracking with a leave management tool. Keep reading for our top choices.

What to Look For in a Leave Management System

This section will help you understand how we settled on the leave management software tools in this post. If you just want to know the best tools for the job (and you trust what we have to say), feel free to skip ahead. But if you want to do your own research and figure out which tool is right for you, this will help you know what to look for.

There are five areas we looked at when assessing these tools. Each is not necessarily equal. For example, some startups may need a more extensive feature set or specific integrations, while for others, price may be a differentiating factor.


Here are some staple features to look for in a leave management solution:

  • Automated leave requests and approvals.
  • A centralized area to view all scheduled leaves (preferably a calendar view).
  • Data and reports that allow you to gain insights on how employees are using their PTO, track trends, send information to other departments (e.g., payroll), and save whatever you need for compliance reasons.
  • Accessibility on mobile (the ability to request and approve leave and view your schedule on the go).
  • Customizable leave types to fit your leave policy.
  • An employee portal or hub where a person can view their leave policy and remaining paid time off allowance.

Bottom Line: feature-rich is good, if you need a lot of features. But smaller startups should value simplicity over a bunch of complicated features.


Your leave management system should make your workflow simpler, not more complex. That’s why you want it to integrate with the tools you already use.

These integrations will differ for each business, depending on what other tools you rely on. Some common examples include:

  • Slack/Microsoft Teams
  • Google Calendar
  • HR & Payroll systems

Bottom Line: find a tool that integrates with other tools you use in your business, and reduces the amount of task-switching you need to do.

Ease of Use

Again, the key is to make your life easier and not add unnecessary complexity to managing human resources in your business.

Many software tools have extensive feature sets that provide a ton of value, IF you can figure out how to use them. The problem is that it takes a lot of time to learn, and to teach your employees how to use these leave management systems.

Look for something easy to set up, easy to understand, and doesn’t require a big learning curve before it starts to provide value. It may be worth losing a couple of bells and whistles for software that doesn’t need a week-long boot camp to figure out.

Bottom Line: the point of leave management software is to make your life easier. Choose something that’s simple and easy to use.


Price will always be a consideration when we’re talking about software. Many startups handicap themselves by paying far too much on recurring software expenses, cutting into profitability.

If the tool delivers enough value (i.e., saving productive hours for you or your HR department and allowing your business to run more efficiently), you can justify a certain cost. Most leave management tools will at least offer enough value to justify paying for them. But it’s certainly something you should consider when comparing two tools against each other – is it worth paying for the more expensive tool?

Bottom Line: the more time and labor hours a tool saves you, the higher price you can justify spending on it.


You may be early stage now, but you won’t be forever. If everything goes according to plan, your business will grow, your headcount will grow, and your needs will too.

A leave management software might work for you when you have ten employees, but will it still work as well when you have 25? 50? 100?

You may also grow to need more complex features, like support for multiple teams and locations, or more extensive employee records and HR reports (these tend to be a must for compliance). You can always switch tools, but this is a headache. It’s better to start with a tool that can grow with you.

Bottom Line: think about whether you’ll be able to continue using this software as your company gets bigger, or if you’ll soon need to go through the hassle of changing tools again soon.

The Five Best Leave Management Software for Startups and Small Businesses

With that out of the way, let’s get to the reason you’re here. We’ll look at five leave management software tools to suit startups of varying sizes and stages, and give our personal recommendation for which tool you should use for your business.


If you want a simple, easy-to-use leave management tool that still comes with all the features small and large startups need, Flamingo is for you.

Flamingo is a leave tracker made for modern, agile startups. It’s perfect for remote teams, enabling asynchronous leave requests and approvals and supporting multiple teams in multiple locations. Also… it’s the leave-tracker that we use ourselves at and our portfolio companies.

The whole process works within Slack, from employees requesting time off, to managers reviewing and approving or denying time off requests to pulling up reports and notifying team members of upcoming leaves.

It supports extensive customization, letting you set up and track different leave types, including vacation days, sick days, and even half days, as well as importing public holidays from anywhere in the world.

It also syncs with calendar apps like Google Calendar. This ease of integration into your existing workflow and the very short learning curve (you can get set up in less than 5 minutes) are big reasons why Flamingo is number one on this list.


  • Deep integration with Slack and calendar apps (e.g., Google Calendar)
  • Flexible configuration (create multiple teams, locations, customizable leave types, etc.)
  • Covers the whole leave management process
  • Fast to set up, easy to use
  • Free for small teams


  • Currently only works for Slack teams


  • Free for up to 10 users, $2 per user per month after (includes free trial)

Google Sheets

A custom leave tracker made in Google Sheets

If you’re running a small startup – perhaps you only have a few team members, and you’re pre-revenue – you could get away with simply using Google Sheets as your leave management system.

The obvious benefit of Google Sheets is that it’s free. Anyone can sign up for a Google Account and set up a vacation tracking spreadsheet. It’s flexible enough to fit your leave policy, and you can create a shared link for your team to view your leave calendar on mobile or desktop.

As a tradeoff, you need to do more data entry, and you’ll have to accept a higher chance of human error. There’s no automated reporting. It won’t be suitable once you scale past a certain point, but if you expect to stay small and have a low budget, it’s a decent place to start.


  • Free software with a Google account
  • Flexible


  • Requires a lot of manual data entry
  • Only so much you can automate
  • Not scalable


  • Free

Kissflow HR Cloud

Now we’re looking at higher-end tools for more established startups.

There are many cloud-based, full-stack HR tools out there, not only handling your leave management system but also things like onboarding, compliance, payroll, etc.

Kissflow HR Cloud is one of those tools. It comes with a range of powerful features, including leave management, and even allows you to set up your own internal company apps and workflows with a no-code app builder.

The downside is that it’s complicated and much more expensive than simpler leave management systems. The minimum you’ll pay is $360 per month or $3600 per year for teams of 20 people. It’s likely too much for a small startup just looking for something to simplify its leave management process.


  • Full-stack HR tool
  • Powerful features designed for the needs of larger organizations
  • Extensive customization possibilities


  • Expensive
  • Complicated


  • $15-20 per user per month


Edays is another tool geared more towards higher-end, established companies. Unlike Kissflow, though, it’s specifically for leave management rather than being a full-stack multi-purpose HR tool.

What it can do for your leave management process is extensive. It gives you a ton of data on employee absence requests and unscheduled absences, making it easy to identify trends like absenteeism. It’s secure and compliant with regulations worldwide, making it suitable for large-scale companies.

It’s not a great fit for small companies, however. The pricing is expensive (the lowest you’ll spend is £1200, which is for teams with 50 employees), and it’s a little time-consuming to set up and use.


  • Powerful and feature-rich
  • Deep reporting features
  • Comes with a mobile app
  • Great customer service


  • Expensive
  • Not suitable for small teams


  • Teams need to request a quote for pricing, but the minimum purchase price is £1200.


Finally, Zenefits is another full-stack HR tool that integrates your leave management system with everything else on the human resources side of your business.

Zenefits is a well-known name in HR circles, trusted by thousands of businesses of varying scales. It handles vacation requests, leave management, scheduling, payroll, and benefits administration.

The cost is not bad as HR suites go, especially if you just want the basic feature set. But it’s still overkill if you’re only looking for a leave management software.


  • Full-stack HR solution – handles onboarding, payroll, benefits, performance management, and much more
  • Well-known in the HR industry


  • Expensive (if you just want a leave management tool)
  • Many features are not available on the lowest plan
  • It may be complicated to get set up


  • Starts from $8 per user per month (paid annually)

Why Leave Management Systems are Important

It’s easy to disregard the importance of a leave management system. It seems like a simple process; say yes or no when someone asks for time off, write it down, and forget about it. Right?

The problem is that it’s time-consuming and error-prone to operate without a proper system in place. It’s too easy to forget to note down when someone asks for leave and get a rude awakening when you turn up one day, and they’re not at the office.

This leads to missed deadlines, unhappy customers/clients, poor team communication, and low levels of employee satisfaction in your team.

If you want to track leave manually and keep everyone updated with upcoming leaves, you can do it manually, but it will take a lot of time and effort. The hourly cost for you or your staff to handle this can easily pay for any number of leave management software tools (especially considering a tool like Flamingo is free for small teams).

The last issue is that you want to reduce friction and make it easy for employees to request time off. Having no system in place invites confusion and may result in more introverted employees overworking themselves due to the stress of it all.

Your leave management system should make this easy and give employees a self-service portal to make time off requests, removing the stress about taking their vacation days or sick leave.

Final Thoughts

A sound leave management system will:

  • Take the friction out of leave requests and approvals.
  • Make it easy to see who has leave coming up, and how many leaves are scheduled at a given time.
  • Automate much of the process and save you and your employees time.
  • Cut out human error.
  • Give you an easy way to get reports and view trends and a bird’s-eye view of your vacation schedule.

If your team is bigger than just a few people, the only way to do this is with a leave management software tool. Choose one that fits your team – if you’re a large business with more extensive HR needs, a full-stack tool like Zenefits might be best. If you’re trying to run your business in a more agile way, and most of your communications happen on Slack, try Flamingo, which is the easiest and more straightforward way to set up an effective leave management system.



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