How to Plan a Successful Software Rollout for SaaS New Products and Enhancements

How to Plan a Successful Software Rollout for SaaS New Products and Enhancements cover

For any SaaS owner or product manager, organizing a successful software rollout can be a stressful, exhilarating experience.

In this article, we’re going to unpack the mysteries of what it takes to put together a truly successful software rollout plan. We’ll start by exploring key steps in the process, then look at some of the most effective tactics to help you form your own rollout strategy.

Ready to get started? Let’s dive in!


  • A software rollout is a term used to describe the process of launching new software (or upgrades) to an existing user base.
  • A software rollout plan describes the set of activities that go into actually releasing that functionality.
  • A successful software rollout plan can be a huge asset to any product manager: it helps you set a clear direction, align your team, and prevent blockers that could derail your rollout.
  • There are several key steps to consider when rolling out a new software upgrade or feature.
  1. First, define your users: who is your new software solution designed for?
  2. Next, set proper objectives and key results (OKRs) to measure success. Then, organize your rollout strategy to meet those OKRs.
  3. Identify and neutralize any potential roadblocks to your software rollout project.
  4. Always consider testing product-market fit before a big rollout.
  5. Finally, you should organize appropriate training, consider user onboarding strategies, gather feedback as you go, and remember to draw from your experience from previous deployments!
  • Here are some best practices to consider throughout your rollout: make your plan adaptable, use fake door tests to gauge demand, utilize a range of in-app comms, use analytics to guide your decisions, and consider a Product Hunt launch to test product market fit.

What is rollout in software development?

A rollout – sometimes referred to as a ‘release’ or ‘deployment’ – is a term used to describe the process of launching new software (or upgrades) to an existing user base. It’s part and parcel of any successful SaaS company, which will constantly be looking to release fixes and enhancements that improve productivity and user experience.

What is a software rollout plan?

A software rollout plan describes the set of activities that go into actually releasing that functionality. A plan will typically factor in several aspects:

  • Key users and stakeholders
  • The complexity of the upgrade
  • Change in experience for users (and whether software training is required)

Why do you need a software rollout plan?

“If you don’t know where you are going, you’ll end up someplace else.”- Yogi Berra

Plans are essential in any software rollout process. They help galvanize a team, move things forward, and take positive steps to get working software into the hands of your users.

Planning has many benefits: Some of the most remarkable ones are:

  1. Boost adoption. Getting users to adopt and value your software is the ultimate goal of any software rollout project. A plan helps facilitate that process.
  2. Prevent blockers. Without a plan, it becomes very hard to anticipate blockers and remove potential bottlenecks to the release process (e.g. ‘Oh no – team X isn’t available for this integration and we’ll have to delay 2 months.’)
  3. Align your team. Software rollouts are complex and need the various teams involved pulling in the same direction. That means your engineers, marketing, support, and product all need to be aligned in your thinking, and a plan helps deliver that.

Steps to consider in a new software rollout process

In this section of the article, we’re going to break down the key steps in any effective rollout of new software:

  • Define your users: who is your new software solution designed for?
  • Set proper objectives and key results (OKRs)
  • Organize your rollout strategy
  • Identify any potential roadblocks for your software rollout project
  • Consider testing product-market fit before a big rollout
  • Prepare necessary software training sessions in-house
  • Plan your user onboarding strategy
  • Gather feedback as you go
  • Bonus: Use your experience from previous software deployments

Who is your new software solution designed for?

First things first: who are you building the thing for? If you can’t answer quickly, chances are you need to rethink your new software rollout plan.

Starting with a clearly defined user (or group of users) will guide your messaging, what the implementation process looks like, the level of documentation necessary, any in-app guidance, and the overall complexity of a rollout plan.

Handy tip: Use product usage analytics to gather insight into how your audience is already using your product. That’ll help inform your decision-making and adapt your rollout plan accordingly.

Set proper objectives and key results (OKRs)

Management guru Peter Drucker famously said, “What gets measured, gets managed.” That’s the key idea behind OKRs: you define a clear set of objectives, and break out tangible results to measure your performance against those objectives.

Take the time to think these through and define them up front: it’ll help you answer the question of whether your launch is a success or not.

Userpilot OKR visual
Distinguish between objectives and the key results you’ll track on the way.

Many OKRs will extend beyond the rollout itself. Here’s an example:

Objective: Boost adoption of new feature X

Key result 1: 50% increase in successful journeys for feature X

Key result 2: X% improvement in NPS score

Define the rollout strategy

At this stage, you’ve defined who you’re launching for and how you’re going to measure success. Now it’s time to get into the nitty gritty of project management.

Here are some key questions to answer that’ll help inform your rollout:

  • Does it make sense to launch in phases (starting with iteration 1, then expanding functionality) or should you go for a big bang?
  • Should you run a small group of beta users to collect feedback and iterate before a wider launch?
  • How far should comms extend? Should you include external stakeholders or only core users?
  • Should your rollout influence product decisions (e.g. going with a simpler option for speed or spending time and effort to fix bugs pre-launch)?
  • Do you separate out your development and implementation team?

Identify any potential roadblocks for your software rollout project

Now you’ve put together a perfect plan. What could go wrong?

The answer is a lot.

All software rollouts are complex, with multiple moving parts to consider and the potential for challenges every step of the way.

The key here is to figure out what could go wrong and put in place clear mitigations – a plan for how you’ll respond if (and when) things don’t go according to plan.

Example 1: Your support team is bombarded with requests for help.

Mitigation: Come up with FAQs, knowledge articles, and a pre-existing communications plan to help them.

Example 2: A key feature doesn’t land with a user group as positively as you’d expected.

Mitigation: Involve users in rounds of testing and prototyping to align expectations and give you the assurance you’ve made the right decisions.

Consider testing product-market fit before a big rollout

Now you might not want to steam all the way in straight away. Many software rollout plans include a smaller launch – a ‘beta’ stage – where a ringfenced user base has the chance to try out new features first.

Beta launches give you a chance to test the water and get a sense of how it’ll land without the risk of all your users rejecting a new feature. You can even have a small launch on Product Hunt opened for a limited number of users, get feedback, and make improvements.

Screenshot of Userpilot beta testing
Gauge whether users have a true demand for your new feature.

Prepare necessary software training sessions in-house

When you launch a new feature, every department on the team should understand what your software does and how it works.

A key part of any launch is to lay the groundwork of that specialist knowledge where it really counts: with your support, customer success, and potentially sales team. That’ll help put your team members in the best possible position to help users adopt your new features.

Plan your user onboarding strategy to boost user engagement and drive software adoption

You should treat any software rollout exactly like you’re onboarding customers: think about the end-to-end journey, what they’re trying to achieve, and how you can help deliver value as quickly and effectively as possible.

Your go-to-market plan should be an example of effective communication and consider all the aspects below: think about how you can use these different elements to drive engagement (and therefore adoption).

Visual of Userpilot customer onboarding process
All of these aspects of onboarding are relevant to consider for your software rollout.

Gather feedback and improve

You can never have a complete understanding of your product, your users, and the process. This means that you should look to constantly gather information on a range of areas as you go. Consider:

  • Analytics of user behavior and performance
  • Different types of microsurveys on overall user satisfaction
  • Feature specific polls to gather insight on ease of use and functionality
  • Performance of your support team (which queries are resolved the fastest, and which the slowest)

Bonus: Use your experience from previous software deployments

Use your experience to help guide each new software launch. Of course, this is tricky if you’re launching an entirely new product, but there’s still a wealth of information you can draw from.

Draw from a range of sources:

  • What were the challenges?
  • How did you overcome them?
  • What went well? What made the biggest impact?

Remember to apply your learnings as you go, and you’ll be in for a successful software rollout.

Software rollout plan best practices

Now we’ve broken down the steps in the process, we’re going to explore some industry best practices you can integrate into your plans. Let’s dive in!

Software rollout plans are not fixed

Remember that while planning is critically important, many of them end up being pretty useless. So much can change over the course of a rollout you need to be ready to adapt and flex.

You should look to gather insight, adapt your rollout plan, and ultimately close the feedback loop with your customers.

Try fake door tests before developing new features

You don’t want to waste your time building new software which nobody wants to use. Fake door tests are an extremely effective way of gauging demand with minimal effort.

Let’s take a look at the example below (built with Userpilot).

Asana shows how a fake door test could capture interested users and judge whether the feature is worth pursuing.

Screenshot of Userpilot fake door test
Identify interested users by seeing who clicks on a fake door test with Userpilot.

As an added bonus, fake door tests help to entice early adopters for beta testing and targeted marketing campaigns.

Screenshot of Userpilot fake door test invite to new feature
You can recruit users for beta testing once you launch a feature.

Use in-app as your main channel for new software and feature announcements

Communication is just as important as launching new software itself. You should prioritize in-app comms to ensure you target users where it counts.

Start with asking yourself the question ‘who does this impact?’. That way, you’ll be able to target distinct user segments.

Screenshot of Userpilot user segmentation
Don’t be general with your in-app comms – target distinct segments with Userpilot.

Choose the right form of communication for the context: for example, a modal is a great way of making a big announcement and grabbing attention.

Screenshot of Userpilot modal
Modals are a perfect way of grabbing attention.

If you’re looking to boost the adoption of a specific feature, you might consider targeted tooltips.

Animation of tooltip in Slack
Interactive tooltips help show your users how to get value out of a feature.

You can also follow up with training sessions and webinars before the big launch.

Screenshot of Userpilot webinar
Product release webinar by Userpilot

There are many ways to effectively announce software updates right in the app. Don’t just rely on one form of comms to solve all your problems.

Use product usage analytics from the start

A key part of rolling out new software successfully is to use data to guide your decisions. Failing to gather and use data means you’re flying blind – and what you don’t track you can’t improve.

Here is a short webinar, where Yazan Sehwail, the co-founder and CEO of Userpilot, talks about product usage analytics in detail.

Product Usage analytics with Yazan Sehwail.

You can pair product usage analytics with heatmaps to understand user behavior on a deeper level, and session recordings to unpack why a user has made a specific decision.

All of this data will help you put together a more comprehensive plan that caters to the needs of your users.

Consider a soft Product Hunt launch to test product-market fit or get your first users

Product Hunt is a marketplace for launching new products (or publicizing big updates to existing products).

One handy tip is to organize a soft launch on that platform to gauge user reaction, generate interest and demand, and ultimately understand whether you’re likely to achieve product market fit.


There you have it, zooming through the world of product launches and software rollouts.

Hopefully, you should now understand:

  • What a software rollout is all about
  • How to create a rollout plan that sets you up for success
  • Tools, tips, and best practices for successful implementation

Want to create in-app announcements for your product launches and get customer feedback code-free? Get a Userpilot Demo and see how you can deliver highly engaging rollouts that delight your users and drive digital adoption.

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