7 Steps for a Successful Software Rollout in an Enterprise-Sized Organization

Let’s look at some steps for a successful software rollout at enterprise organizations, with help from Eagle Point Software’s Customer Success Team Lead, Amanda Wachendorf.


  1. Engage with leadership
  2. Outline clear objectives
  3. Use multiple communication pathways
  4. Emphasize the benefits
  5. Make it fun for them
  6. Understand that adoption may be gradual
  7. Listen to feedback and address pain points 


Below, we’ll expound on these steps for a successful software rollout!


Engage with leadership

Your very first step is connecting with the right people in leadership positions across your organization. “Getting alignment with the leadership team members who directly oversee teams will help solidify messaging and ensure users are empowered to leverage the new software tool,” Wachendorf says. Make sure they know what’s coming and have the resources to communicate changes to their teams.


Outline clear objectives

Before you can have a successful rollout, you need to know what success will look like. You might aim for a certain percentage of user adoption by a specific month or successfully using the software in a certain amount of projects. (Our Customer Success team can help you define your own organizational objectives when rolling out Pinnacle Series!)


Use multiple communication pathways

“Many times over: users are busy,” Wachendorf emphasizes. “Communicate with them in different ways to ensure the messaging is clear and consistent. Organizations often lean too heavily into email. Also incorporate intranet posts, blogs, newsletters, posters, live events, and more! Using various methods of communication is key, but repetition is just as important. Users will need to hear the message several times before they begin to absorb it.”


Emphasize the benefits

Employees will be excited to use the new software if they understand how it will improve their days at work! “The messaging should directly tie into how users will benefit from the new tool,” Wachendorf advises. “A new software for the sake of a new software will fall flat, but if you can tie to a challenge or pain point your users have, they will be more interested in the solution.”


Make it fun for them

Another way to ramp up user adoption: introduce a spirit of friendly competition with rewards and gamification! “Build a leaderboard or have a contest,” Wachendorf suggests. “This will help to break up the monotony of work.” 

One idea our CSMs enjoy for a Pinnacle Series rollout is a scavenger hunt, where users are tasked with using the e-learning software to find answers to various questions. It gets them familiar with the software, and you can reward a successful hunt!


Understand that adoption may be gradual

In a normal software adoption lifecycle, users tend to trickle in — you have the innovators (the very first people to use it), then early adopters, early majority, late majority, and “laggards” who are the most hesitant to change the status quo. This is normal! Give teams time to adjust and get used to the new program. 


Listen to feedback and address pain points 

Are users enjoying the new software? Is there anything they’re struggling with? Do they wish they had better training to help with certain processes? Give employees and teams a space to submit their feedback or send out mid-rollout surveys to see if there’s anything to improve.


Want to follow these steps for a successful software rollout while introducing Pinnacle Series to your enterprise organization? Get in touch with our team to explore Pinnacle and learn how we work alongside you for a smooth transition!

If you’re already a Pinnacle Series subscriber, log in now to explore the training libraries we have to help with your next software rollout.



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