A Finance Leader’s Guide to Supporting Software Deployment in a Remote-Work World

Like it or not, the remote workforce is here to stay. The trend that began pre-pandemic has escalated at warp speed, with analysts predicting that 25 to 30% of personnel will be working for home, at least multiple days a week, by the end of 2021. 

While this mass office exodus has fundamentally changed day-to-day business, it has also significantly increased adoption challenges when new software is deployed. If organizations don’t create a new strategy for rollout, employee training, and put a more effective feedback mechanism in place for continual optimization, the software won’t get used as intended, and that investment will be wasted.

The answer? Finance leaders have to play a greater role than before during the development of these deployment and change management strategies, as well as actively guiding their execution—or  they won’t realize the return on their investment.

Even if it means stepping outside of their comfort zone, finance leaders have to be and stay actively involved in these four areas of software deployment: stakeholder engagement, rollout strategy, change management, and software/process optimization. 


Stakeholder engagement: It takes a (remote) village

Although finance leaders were traditionally involved in software selection, much of the deployment was compartmentalized: marketing communicated the change, the trainers held training sessions, and IT made sure everything worked. And although there were planning meetings, many critical conversations happened organically—passing in the hall or popping into a colleague’s office to give a head’s up. 

With a remote workforce, it is more important than ever for finance leaders to engage more stakeholders (and the right stakeholders) as part of the planning process. 

  • Identify the specific areas the software impacts. Is it one or two departments, or a corporate-wide rollout? 
  • Meet with the appropriate department heads to determine the optimum rollout timing, based on their area’s activities and deadlines. In a remote environment, schedules are much less transparent. You don’t want to plan your rollout, only to discover that sales and marketing are prepping for a virtual client conference, or another area is having a hardware upgrade at the same time.  

Use this information to develop your schedule, including a hard-and-fast cutoff date when the grace period ends, and all users have to start using the new software and processes.  


Rollout strategy: More is better

No matter how much time you’ve allotted for successful software deployments in the past—add more. Deployment in a remote environment requires more planning, more communication, and different considerations.

  • Determine whether a staggered rollout timeline or a blanket rollout makes more sense for your organization. Of course, this decision depends on your required timeframes, the number of employees transitioning to the new software, and the capability of your current infrastructure. If timeframes allow, consider piloting the program with a strategic mix of users first—both to work out the kinks before rollout, and develop some in-field experts who can help their peers during the broader rollout. 
  • Identify what kind—or combination—of  training will be most effective for your new users in their new environments. While online, self-guided instruction may have been a viable option in the past, employees now have a number of different things competing for their attention at home. Would a more structured approach make more sense? Can you do “live” training for different groups, allowing for interaction, screen shares and user questions? Or do time zones, budget constraints, or basic logistics require you to record one group training and share this with users company-wide? 
  • Will the training be mandatory, or is it a better cultural fit to incent users to complete the program, or gamify participation with an individual or departmental competition? 

It’s important to note that although a remote workforce does require a more robust rollout strategy, reviewing historical data, and identifying  any roadblocks that occurred in the past are essential to refining your go-forward strategy. 


Change management: Driving adoption by getting personal

Although driving adoption has always benefitted from top-down support, finance leaders’ stake in the game is more significant than ever in the work-from-home model.  Rethinking your approach will maximize adoption—and that all-important ROI.



Communicate the coming change early and often, and work with department heads to reinforce the message. Make sure your users not only know what’s coming, but have a clear understanding of:

  • When they’ll be trained
  • Where to get support
  • Who can answer questions
  • When they have to be fully transitioned to the new software

It’s also important to assume you’ll need to repeat a lot of information, including links to training, password resets and portals. Consider making use of an intranet or developing a separate internal website just for communications around this initiative—as well as a means of driving users to these vehicles. 


Support strategy

Support strategy is a make or break for adoption. Because people can’t stand up and ask questions over a cubicle or access a trainer roving the office the week of go-live, you have to consider a more robust support model. 

It starts with knowing who your audience is, its size and your users’ skill levels. Then, based on these factors, identify what combination of support functions is the best fit:

  • Message boards and user forms, where power users help those with questions.
  • An online resource with chat support.
  • Multiple central, regional or local Point-of-Contacts within each department.
  • A human-staffed 12-hour or 24-hour phone  hotline, until the number of calls falls below a certain threshold.
  • Or, any combination of the above.


Peer advocacy

In a traditional software rollout, organizations rely on peer chatter to help drive adoption—one or a group of users “talking up” the new technology, its ease of use, or how a specific feature saved them time or aided them in some way.

Identifying how to replicate this breakroom chatter in a virtual environment can be challenging, but, even if it occurs on an employee communication system, or as success stories in employee news briefs, you’ll gain traction. And don’t forget to ask your advocates and power users what they recommend to spread the word. Chances are, they’ll come up with an effective approach you hadn’t considered before. 


Ongoing optimization

Finally, you have to find a feedback mechanism for process optimization that works with the home-office crowd. Surveys can work, but you may have to be creative to gain response, like entering respondents in a drawing or having department heads distribute (and collect) these online forms during virtual meetings. 

In a remote environment, it is particularly critical to analyze your usage data, and identify where your low utilization is. If you have engaged those department heads early on in the planning process, you can seek out their help in finding and addressing that root cause. 

Also consider having a virtual meeting with those low-use groups to discuss why they’re having issues, or offer up additional training or individual help, if required.

No question, COVID-19 has changed “business as usual” for us all, ushering in a new, virtual era for companies in every industry, everywhere around the globe. By adjusting to these new norms, and getting more involved in software deployments, finance leaders can ensure their software investments continue to pay dividends for the company, their users and the industry they serve.



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