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Dropbox Business - Enterprise vs Office 365 comparison

 

Comparison Buyer's Guide

Executive SummaryUpdated on Nov 2, 2025

Review summaries and opinions

We asked business professionals to review the solutions they use. Here are some excerpts of what they said:
 

ROI

Sentiment score
6.0
Dropbox Business users reported varied ROI experiences, appreciating features and security, though some struggled to establish clear financial gains.
Sentiment score
6.3
Office 365 offers cost savings and productivity boosts via subscription models, integrated tools, time savings, and enhanced security.
Internal surveys show a 20% increase in team productivity due to better collaboration in Microsoft Teams.
System Engineer at a retailer with 10,001+ employees
Though money is not saved directly, time is saved significantly due to its user-friendliness, reducing the need for extensive user training.
IT operation manager at a tech vendor with 1,001-5,000 employees
 

Customer Service

Sentiment score
2.9
Users find Dropbox intuitive, with generally good support available 24/7, though some experience delays and manage support independently.
Sentiment score
4.2
Office 365 customer service is praised for efficiency and expertise, with suggestions for improved communication and additional support channels.
Dropbox offers 24-hour support, both through chat and limited hour calls.
Research Analyst at Counterpoint Research (Counterpoint Technology Market Research)
We provide the support ourselves and do not have any support straight from Dropbox.
Measurement Manager at A3E Ingenieros
I really have not hit many brick walls where I have had to ask for customer support.
Business Process Manager/ Educational Technologist at a educational organization with 1,001-5,000 employees
At times if you're trying to use their online support, they'll send you to an article that may or may not have anything to do with what you're looking for.
Controller/HR Manager/IT Manager at a manufacturing company with 11-50 employees
For complex issues, premium support tickets are usually handled within a few hours, providing a great experience.
System Engineer at a retailer with 10,001+ employees
 

Scalability Issues

Sentiment score
7.2
Dropbox Business - Enterprise offers scalable plans for various needs, with flexible options requiring payments for added storage or users.
Sentiment score
7.5
Office 365 is highly scalable, accommodating diverse global teams efficiently, with licensing costs as a key consideration.
Office 365 offers virtually limitless scalability.
System Engineer at a retailer with 10,001+ employees
Whenever scaling up is required, procuring additional licenses is easy unless it is under an EA plan.
IT operation manager at a tech vendor with 1,001-5,000 employees
 

Stability Issues

Sentiment score
8.1
Dropbox Business - Enterprise is highly stable, rated ten out of ten, with minor issues like syncing delays in low bandwidth areas.
Sentiment score
7.4
Office 365 is praised for stability and reliability, with occasional performance issues and Microsoft’s valued 99.99% uptime guarantee.
Microsoft provides a 99.9% financially backed guarantee.
System Engineer at a retailer with 10,001+ employees
The integration capabilities of Office 365 with Word, Excel, and Outlook with OneDrive for cloud storage have been smooth and work well.
Controller/HR Manager/IT Manager at a manufacturing company with 11-50 employees
At this time, whatever they have meets the needs, and they are expanding the number of participants to Team meetings and other features.
IT Administrator at a university with 51-200 employees
 

Room For Improvement

Dropbox Business - Enterprise could improve file sharing, security, storage, pricing, integration, UI simplicity, real-time collaboration, and scalability.
Office 365 users seek language expansion, improved compatibility, better support, refined features, and more training resources for optimal use.
Sharing documents with other people in the same division or department and being able to work without downloading the file would be ideal.
Measurement Manager at A3E Ingenieros
One area of improvement would be to allow multiple users to edit a file simultaneously and see edits in real time, similar to OneDrive.
Research Analyst at Counterpoint Research (Counterpoint Technology Market Research)
When you try to sync the files in Dropbox, it actually puts a copy of the file on your laptop, so it sucks up all of your memory.
Business Process Manager/ Educational Technologist at a educational organization with 1,001-5,000 employees
I believe the choice of office apps often depends on the existing ecosystem of the business, and since Office 365 has comprehensive coverage, I am not missing any features that the competition provides.
React Native Team Lead at Visible Magic
The interface for the security and compliance center could be simplified.
System Engineer at a retailer with 10,001+ employees
It has been observed that support personnel often lack hands-on experience, and more training is required.
IT operation manager at a tech vendor with 1,001-5,000 employees
 

Setup Cost

Enterprise users appreciate Dropbox Business for competitive pricing and flexibility, though some desire better discounts compared to alternatives.
Office 365 provides competitive pricing and diverse plans, though licensing can be confusing and improvement is needed in cost transparency.
the cost of using the Microsoft ecosystem is higher than the combined cost of using Notion and Slack.
Project Management Associate at MPost
My experience with the pricing or licensing of Office 365 is that a lot of times we've gotten them when they've been on sale, so we've had really good pricing for the Microsoft products.
Controller/HR Manager/IT Manager at a manufacturing company with 11-50 employees
My experience with pricing, setup cost, and licensing for Office 365 is that it is moderate.
IT operation manager at a tech vendor with 1,001-5,000 employees
 

Valuable Features

Dropbox Business - Enterprise provides seamless file sharing, strong security, and integration, enhancing productivity for both individuals and teams.
Office 365 offers cloud integration, real-time collaboration, secure sharing, extensive storage, productivity apps, AI automation, and user-friendly interfaces.
It also features an admin console where we can easily manage users, see which user has access to which content, and how much space they are consuming.
Research Analyst at Counterpoint Research (Counterpoint Technology Market Research)
I do enjoy the family sharing plan, so my entire family can use my one plan and my data storage, and we can have shared files or private areas for their own files.
Business Process Manager/ Educational Technologist at a educational organization with 1,001-5,000 employees
It has improved productivity and functionality by providing all necessary tools in one suite.
CCC at FlowSec
The most valuable feature is SharePoint, where we can easily put files and make them accessible to any person who has access.
Project Management Associate at MPost
Office 365 has positively impacted my organization by making the salespeople more accurate because they've been able to use the features in Excel instead of relying on the calculator or adding machine.
Controller/HR Manager/IT Manager at a manufacturing company with 11-50 employees
 

Categories and Ranking

Dropbox Business - Enterprise
Ranking in Content Collaboration Platforms
3rd
Average Rating
8.2
Reviews Sentiment
6.7
Number of Reviews
91
Ranking in other categories
Cloud Storage (2nd)
Office 365
Ranking in Content Collaboration Platforms
1st
Average Rating
8.6
Reviews Sentiment
6.2
Number of Reviews
152
Ranking in other categories
No ranking in other categories
 

Mindshare comparison

As of January 2026, in the Content Collaboration Platforms category, the mindshare of Dropbox Business - Enterprise is 8.8%, up from 8.8% compared to the previous year. The mindshare of Office 365 is 10.3%, up from 4.7% compared to the previous year. It is calculated based on PeerSpot user engagement data.
Content Collaboration Platforms Market Share Distribution
ProductMarket Share (%)
Office 36510.3%
Dropbox Business - Enterprise8.8%
Other80.9%
Content Collaboration Platforms
 

Featured Reviews

NancyHartman - PeerSpot reviewer
Business Process Manager/ Educational Technologist at a educational organization with 1,001-5,000 employees
Family sharing and personal backups have improved how I manage and access my files anywhere
I am not fond of their syncing. Their file syncing is very clunky, so I am not a real fan of the file syncing. I think Box does a much better job of the syncing of data onto desktops and laptops. When you try to sync the files in Dropbox, it actually puts a copy of the file on your laptop, so it sucks up all of your memory. Whereas with Box, I can sync files into my file explorer and it is still cloud-based. They have not saved the file physically onto my laptop. They save it in the cloud and it just does a temporary download and then it uploads again, but that file is not saved on my laptop. Whereas with Dropbox, anytime you want to sync on your laptop, it actually does save it. There is a way to set it up, but it takes a lot more work and effort and I have never been able to get it to work the way I want it to work. So I just do not sync my files with Dropbox on my laptop. That limits my ability to use Dropbox from my work laptop because my work laptop just does not have any memory at all on it. They give the bare minimum of memory and say that it should all be in the cloud anyway, so you do not need to have that much storage space. So I cannot even access Dropbox from my work laptop and have to use the browser version of Dropbox if I need to access my Dropbox from my work laptop. Within the company, it is a personal choice. Our company has not dictated what cloud service to use. As long as it has all the security measures that meet the standards of our IT department, anyone can use whatever cloud service they want. For example, our company is not allowed to use Google because Google is not a secure cloud service in the estimation of our IT department. So there are cloud services that we are not allowed to use, but from the five to seven different services that they give us to choose from, we all can find what meets our needs.
BasilJiji - PeerSpot reviewer
System Engineer at a retailer with 10,001+ employees
Collaboration has transformed how our teams work and Copilot now drives faster daily decisions
The interface for the security and compliance center could be simplified. It changes frequently, which can make it somewhat difficult for admins to stay up-to-date on where specific settings are located. The compliance center modification or improvement of Office 365 needs to be introduced. The rest of the features feel acceptable to me. The reason it is not a ten is because of the complexity of managing the vast array of admin settings, which requires a specialized IT team. Even though it meets industry standards for decent security compliance such as SOC and HIPAA, the complexity of managing the admin settings needs to improve.
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Top Industries

By visitors reading reviews
Performing Arts
10%
Manufacturing Company
9%
Financial Services Firm
6%
University
6%
Computer Software Company
15%
Outsourcing Company
10%
Manufacturing Company
8%
Performing Arts
7%
 

Company Size

By reviewers
Large Enterprise
Midsize Enterprise
Small Business
By reviewers
Company SizeCount
Small Business40
Midsize Enterprise19
Large Enterprise34
By reviewers
Company SizeCount
Small Business62
Midsize Enterprise29
Large Enterprise70
 

Questions from the Community

What do you like most about Dropbox?
For me, the biggest thing is version history. I can easily go back and view older versions.
What needs improvement with Dropbox?
One area of improvement would be to allow multiple users to edit a file simultaneously and see edits in real time, similar to OneDrive. In Dropbox, once a file is opened on one system, it locks the...
What is your experience regarding pricing and costs for Office 365?
I didn't inquire about the specific costs of transitioning from the previous tools. However, I was informed that the cost of using the Microsoft ecosystem is higher than the combined cost of using ...
What needs improvement with Office 365?
I don't have any ideas off the top of my head at the moment about what I would improve about Office 365. I can't think of anything that frustrates me about the tools. I mentioned that I use Copilot...
What is your primary use case for Office 365?
We use the Microsoft Office 365 suite for personal purposes. We use Teams for communications, and we use Azure DevOps for some of our workflow management. I use Office 365 for Outlook for emails. I...
 

Also Known As

No data available
Microsoft Office 365, Office 365 Enterprise, Office 365 Enterprise E1, Office 365 Enterprise E3, Office 365 Enterprise E5, Office 365 ProPlus, Office 365 Business, Office 365 Business Essentials, Office 365 Business Premium, Office 365 F1
 

Overview

 

Sample Customers

Vita Coco, BCBGMAXAZRIA Group, Centric Project, Kayak, FourSquare, Asana, Huge Adversting , USA Gymnastics, Appen, Valliant, Radio Lab
Me & the Bees Lemonade
Find out what your peers are saying about Dropbox Business - Enterprise vs. Office 365 and other solutions. Updated: December 2025.
881,082 professionals have used our research since 2012.