The 4-Step Guide to Building Enterprise Software that Users Love

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Lo stesso prodotto con un nuovo aspetto! HelloSign è diventato Dropbox Sign!

”Enterprise” had become a dirty word when it comes to software.

It has a reputation for being overbuilt, underpowered, slow, clumsy, siloed, hard to work with, and generally full of—pardon our French—bullsh*t.

Unfortunately, this is in direct opposition to what the modern enterprise actually needs. Software that’s fast. Software that’s flexible. Software that delivers value to both business users and customers. Software that’s as easy to use as a cell phone.

Why? Because at the heart of the enterprise lives the actual people who are getting sh*t done day in and day out.

And they, these real-life people, need to be able to use the software that empowers customers and makes the entire enterprise a success.

Building enterprise software today has to be a people-first process.

Yet, the majority of workplaces still seem to be missing this point.

A graph showing technology significance on millennials in the workforce

We get it, there are a lot of moving parts that make building enterprise software difficult, and we’ll address that today. But what we’ll also address is how project managers can peel back the layers of politics, ego, and other bullsh*t to focus first on what business users actually need so they can help create enterprise software that doesn’t suck.

Intrigued? Read on.

Why Is Enterprise Software So Often Over-Complicated?

First of all, it’s only fair that we acknowledge that some complexity is par for the course when it comes to enterprise software. These apps often have to meet the needs of thousands of users in different departments and different locations—all while following strict security and compliance guidelines.

However, unnecessary complexity is often introduced as early as the buying stage, where C-level executives—instead of anyone who’s going to come remotely close to actually using the software—start making crucial purchasing and customization decisions.

From here, the undue complexity only ramps up as multiple stakeholders with multiple priorities get involved—ruining any chance at an elegant solution for users.

It’s also difficult to make the effort to develop modern, easy-to-use enterprise software when complex systems still dominate the market. Moving an entire enterprise to a new software platform is expensive and time-consuming, so it’s no surprise that businesses are reluctant to spend the time building or money buying a better system. Unfortunately, this takes the pressure off of software producers to actually modernize their products and leaves developers with a passion for usability with an outlet.

A Dilbert cartoon strip

While some complexity is certainly to be expected in the enterprise software world, there are plenty of factors that unnecessarily compound it and keep outdated practices in place—but it doesn’t have to be that way.

Here’s how to create enterprise software that’s not a total pain in the a*s to work with.

Your Guide to Building Enterprise Software That’s User-Friendly

As technology becomes a part of everyday life, enterprise software creators have begun to build programs that better mimic the experience of user-friendly consumer applications.

In fact, by 2022, 70% of software interactions in enterprise businesses will take place on some decidedly user-friend platforms—mobile devices.

The next four steps will help you get in on this transformation early and build a user-friendly enterprise platform that garners great adoption rates—which you will absolutely need when it comes to generating ROI, increasing employee productivity, and reducing training time and costs.

1. Develop and Honor User Personas

The best way to develop enterprise apps that people want to use is to get to know those people: Who are they? What’s their level of technical aptitude? What will they use the software for?

After taking the time to gather all this information via one-on-one interviews with real users, you need to organize your data into user personas.

User personas are characters that represent your key users and are informed by real data from your target audience. Ideally, a user persona should at least include:

  • A fictional name and photo
  • A job title and responsibilities
  • Demographics including age, education, location, etc.
  • The goals and tasks they will use this software to complete
  • Their physical, social, and technological environment within your company
An illustration and description of a software user persona

Check out’s informative guide to learn more about the benefits of user personas, the best practices for developing them, and several examples of how to structure them.

Now, what are you actually supposed to do with these user personas? Use them to guide how you build and prioritize features in your enterprise application!

Unfortunately, user needs can sometimes fall by the wayside when product managers and developers are working with a host of different priorities and limitations, tight time frames, and even tighter budgets.

That’s why it’s important to dedicate at least one person on your team to focusing on usability and how functionality lines up with user personas throughout the development process.

The best fit for this role is someone with a connection to usability—whether they’re a user experience (UX) designer or have experience elsewhere in the usability field.

2. Mix in Enterprise Needs

While it’s important to make your enterprise software as user-centric as possible, you also have to remember that people won’t be able to use the software at all if your organization gets shut down due to security breaches, compliance issues, inability to scale, and other issues that can result from poorly-planned enterprise systems.

So, with your user personas in place, it’s time to take a second pass over your feature list and make sure you’re also addressing some of the biggest enterprise software concerns, including:

Security and Privacy

Security is probably the first thing any enterprise software builder or buyer thinks about when it comes to introducing a new system, so start with making sure your software will meet strict security and privacy standards—and that these standards continue to influence the development of the entire app.

Some critical questions you should be ready to answer and “show your work” for when it comes to security and data privacy are:

  • How is data is stored?
  • Who has access to important data and how is their identity verified?
  • How is data encrypted as it’s transferred?
  • How strong is our encryption?
  • What level of security monitoring is taking place?
  • What safety nets are in place in case there’s a breach?

For an example of the kinds of security and privacy measures you should be taking—and the best way to proactively document your efforts for internal and external use—take a hint from HelloSign’s Security page, where you can learn about our information security program, audit trails, encryption, reporting, and plenty more.

Speed and Performance

Business users and customers alike won’t be happy with a slow or unresponsive system.

This is why almost any enterprise will have critical performance and speed requirements that all applications and APIs must meet before they even think about adopting them. Here are some common questions you’ll have to answer to show how your software stacks up against speed and performance demands:

  • How many requests per second can the application (and any APIs) handle?
  • How many requests can be sent simultaneously through any APIs?
  • What is the average latency for requests?
  • How much uptime can you guarantee?

The best thing you can do to answer these questions satisfactorily is to get an up-to-date list of requirements and check your software against them early and often throughout the development process.


Compliance used to be a bit simpler than it is today. It used to be that if you were in a regulated industry—healthcare, finance, government, etc.—there were specific regulations with which you had to comply.

While you still have to watch out for those regulations, now there are also regional compliance concerns such as the GDPR in Europe, the California Consumer Privacy Act, and many more that depend completely on your location and the location of the consumers you serve.

Compliance is not an option. If you don’t already have a compliance professional on your team, we highly recommend bringing a consultant in to make sure you’re following the right rules and building the right tools to keep everything in check.


We can’t think of a single enterprise business that works with just one vendor. Instead, almost all large organizations cherry-pick the best tools to complete each job—meaning there will always be new systems with which your software has to play nicely.

Is your software prepared for maximum interoperability—even when legacy systems may not be? Are you equipped to handle single sign-on (SSO) integration? Can you seamlessly work with existing ticketing, HR, payroll, CRM, and other tools that form your organization’s ecosystem?

Again, HelloSign is a great example of enterprise software that is purpose-built to work with other technology like G Suite, Salesforce, Slack, and even Zapier so you can continue to power your business with third-party integrations.

3. Conduct Usability Testing

The necessity for usability at both the individual and organizational level makes testing enterprise software a complex, and critical, task.

In fact, Jakob Nielsen (co-founder of the Nielsen Norman Group) gave enterprise usability its own definition: “ … how the system impacts the company over time, including issues in administration, installation, and maintenance.”

With the needs of the user as well as the business in mind, here are just a few techniques that your usability champions can use to conduct usability testing on enterprise-level software:

Implement Training Into the Test

Unlike consumer software, enterprise apps almost always come with some level of training. This fact complicates usability testing because, while the system was designed to be used after some kind of introduction, you don’t want to provide any “coaching” that can muddy first impressions.

To help overcome this conundrum, make the experience as close to “true” as possible by implementing training practices right into the usability testing process. Provide training prompts and materials, ask users to complete certain tasks multiple times, etc. This should help identify persistent usability concerns while sifting out “issues” that will be solved during training.

Field Studies

Watching how employees across the organization use your software “in the wild” will provide the best context as to how usability impacts both individual tasks and organizational goals.

For example, you may observe how individual developers use the software to complete a task to better understand the impact it will have on overall sprint completion.

An illustration showing the the observations Deloitte saw after incorporating design and development of an ERP for one of their clients

4. Launch with Care


Anyone who’s ever been involved in introducing a new tool to an existing team has experienced it.

Whether it’s a reluctance to add training tasks to their overflowing workload or concern over how new software might challenge their job, there are plenty of valid reasons that an employee might resist welcoming your new enterprise software with open arms.

Luckily for you, we’ve seen pretty much every iteration of resistance after years of helping organizations implement smart workflow software and we’ve written about it.

Check out our guide to rolling out a new digital tool to your team, which will take you from introducing the software all the way through gathering and implementing feedback.

How Will You Start Building Enterprise Software Without All the Bullsh*t?

If you want to create enterprise software that increases your employee productivity and customer satisfaction while generating a return on investment, then it’s time you cut through the bullsh*t that surrounds enterprise applications and get started on our proven process of developing user personas, documenting enterprise needs, conducting usability testing, and finally launching with care.

To see how we put our money where our mouth is by overhauling the HelloSign website to empower our customers with an even more flawless eSignature user experience, read our blog post: HelloSign Unveils a Cleaner, Simpler UI to Empower Users.

Better yet, check out our easy-to-use software for yourself by signing up for one of our free or affordable eSignature packages.

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