When Dan Cohen joined The Amenity Collective in 2018, his mission was to turn a host of siloed data and mismatched systems in a decentralized environment into an integrated platform that could help the organization scale.

The company mainly served as a holding company for several hospitality and lifestyle services businesses that it had acquired, including American Pool and Heartline Fitness.

Fast forward to 2022, the final piece of the puzzle was to finish building out the integrated platform and digitizing services through a new SaaS vendor, Workday. 

When companies switch software providers, it can rock the status quo. For employees, the change can impact day-to-day work. It’s on technology leaders to reduce friction, limit frustration, engage stakeholders and foster communication to ensure a migration goes smoothly.

For The Amenity Collective, changing software providers was no small feat. 

“There was a really big change management process that, of course, comes along with any big transformation like this,” Cohen said. 

Cohen leaned on best practices from Workday regarding when to engage stakeholders and trainings for different user groups.

“It was a big focus and took probably one to two months before we fully launched to make sure that everyone was prepared, ready and able to make the transition,” Cohen said.

The pre-migration prep

Depending on the end-user impact — and their loyalty to a piece of software — moving from one provider to another can be painful without adequate communication.

Throughout Dara Meath’s tech leader career, she has changed software providers due to poor performance of the vendor, cost models, the vendor’s future business plans and because a solution wasn’t the right fit anymore.

No matter why a change is happening, Meath, SVP and CTO at Build-A-Bear Workshop, said the first step is to sit down with a committee of current end users and identify what they like, what’s working and what could be better about the tool.

“It’s a conversation to be had not just within the technology department, but also those user communities that are touching the tool, because you don’t want to make a change that will adversely affect others and they’re not privy to the opportunity to make the change alongside you,” Meath said. 

When considering vendors, Meath looks at what’s best for the company, what fits well in the infrastructure and tech stack, tool offerings, cost of implementation and how well the vendor understands the business. 

Meath communicates her findings with stakeholders, end users and others involved in the process. That way, everyone has a realistic understanding of what is out there and what will work best based on budget restrictions and usability.

“Do technologists love the current tech stacks? Absolutely, in many ways,” Meath said. “You get comfortable, you’re using it, it’s easy and changing never feels like a good thing, but I have conversations with them to give them the positive side.”

For members of other business units who might be impacted, messaging shouldn’t change, according to Meath. Technologists working on back-end infrastructure don’t relate to people that are using it in finance unless the two parties are brought together. 

“Give extra attention to both the emotional and organizational leaders in the group,” Jeff Golterman, managing director of SoftwareReviews, a division of Info-Tech Research Group, said in an email. “Win over the biggest voices, and you will win the rest of the users.”

In the room where it happens

Build-A-Bear Workshop has a software renewal coming up this quarter. In preparation, Meath held a meeting with leaders from departments using the solution, a vendor representative, IT staff and a project manager.

“If you do your meeting separately, you will have two separate ideas, two separate opinions and two separate understanding of what we should be doing,” Meath said. 

To ease transitions, when Meath has a meeting in person, she brings food in for staff and puts emphasis on team building. 

“Laughter goes a long way in any of these things that you’re doing because people get very serious when technology changes, and the way that we try to communicate it is so serious too,” Meath said. 

Along with food, Meath suggests planning an icebreaker or team building exercise to warm up the room.

Think about timing

For technology leaders, ensuring adoption means venturing outside the IT department.

“Be prepared for compromise but also escalation in case of blockers or conflicts,” Christian Richter, chief customer officer at SaaS provider LeanIX, said in an email. “Having a clear visualization of your roadmap [and] acting as a single, accessible source of truth will be vital for achieving consensus.” 

Timing and forethought are critical to success.  

If a tech stack no longer supports business goals, any time is the right time to change software providers, according to Richter. But for some enterprises, the right time to change can depend on business peaks and valleys. 

The Amenity Collective is a seasonal business in which the employee population quadruples between Memorial Day and Labor Day, according to Cohen.

“We have to be very careful about when we launch new things, because there's such a large focus on scheduling and managing a large customer base that balloons along with our employee base, so we had some restrictions around when we could go live based on making sure we had a smooth transition in and out of the season,” Cohen said. 

Taking into consideration when the busy season is for employees impacted by a software change is critical to reducing friction. When people have more work or are busier, introducing a new tool can cause frustration and slow adoption. 

“I think the one thing that I’d probably do differently is plan for longer timelines,” Cohen said. “It’s really important to make sure there’s buy in and engagement across the spectrum, both from a job function perspective and service lines, and that consensus and engagement takes time.”

Even businesses without seasonal workers frequently have milestones during a certain part of the year. 

“For example, if you are swapping in a new CRM platform for your sales force, you would want to do that as part of your new sales year kick off,” Golterman said. “This keeps the inevitable disruption within a window where you can recover and see your users take the time to ramp up and get productive.”

Making sure your IT team is in the loop and ready to assist during transitions can reduce pain points, too.

“Assume higher than usual levels of calls to your service desk — put on more staff and open up more hours,” Golterman said. “Any system worth investing in is driving greater levels of productivity, and with today’s remote workforce, you can expect those extra calls to the service desk at night and other odd hours.”