Writing Sample (Employee Spotlight) - Amy Westerman of FlexManage
- Brittany Langmeyer
- May 16, 2020
- 5 min read
Company: FlexManage
My Role: Digital Marketing Specialist
Amy Westerman’s talent in O365 migrations shines with FlexManage’s DCS team

Amy Westerman knew that FlexManage was the right fit. At least that’s how she explains it. In 2014, she sought out the firm’s dynamic Deployment Coordination Services practice. And it wasn’t too long before she decided on a career change and was convinced that working at FlexManage was the right move. This is the story of her path to the FlexManage Family.
During the early years of her career from 2005 to 2012, she worked at Turner Broadcasting as a manager for the System Assurance and Operations Windows Group, responsible for leading engineers through projects in Exchange Active Directory, Virtualization, Patching, and the like. Eventually, she got so deeply immersed in Office 365 (O365) from a technical perspective that she became an engineer herself, turning into a management and execution powerhouse for these types of projects. “I still, to date, understand O365 extremely well, technically and everything… so [I realized] that the best thing for me to be doing would be to program manage and have projects underneath me,” said Amy.
Seeking a new challenge, she pursued positioning herself to lead new strategies into the organization for all collaboration tools. In 2014, she was promoted to the position of program manager for Turner’s Enterprise Messaging & Collaboration group. “[I considered] myself more of a change leader, understanding the technical aspects and strategy around what we do,” Amy explained.
And what eventually led her to find FlexManage was her desire to push services into the cloud. She knew that modern business was going in this direction, and so she’d often tell her supervisors that moving into the cloud was no longer a trend, but something they must do or risk serious data disasters down the line.
During an O365 migration in 2015 for Turner’s users, Amy was concerned that the job was something that she might not be able to tackle and lead as a single person. She explained that migrations aren’t just about the details of what needs to get done, but there are many other elements that are involved, such as timeline and status communication to the entire company or ensuring that stakeholders understand what’s going on while engineers are working on their devices. “I needed a plan for execution. It was just too high-level,” said Amy.
She turned to Microsoft for help, and that’s when they recommended FlexManage and our Deployment Coordination Services (DCS) practice as the solution to all her O365 migration project problems. She set up a meeting with Kris Gronert (pictured below), the practice director for DCS at FlexManage.

“Kris explained how the technical parts of the migration would work, but he also said that there’s many aspects that I still haven’t thought of. So I wanted FlexManage to not only do the migration, which is the scheduler role, but I also wanted their project management skills, as well. Their project manager was there to help me think and move a step ahead of what needed to be done,” explained Amy.
So it became official – Amy was able to launch an O365 migration project at Turner with the help from FlexManage’s DCS team. And the first thing that stood out to her about the team was their integrity and transparency.

“What I first loved about FlexManage was the negotiation around the contract,” said Amy. “We did a time and materials contract, they broke it into a bi-weekly basis and they were extremely accurate in their estimations. And when something came up [during the project] that was outside of what the contract was, they told me before it happened, not after. Just total integrity from the start.”
So what made FlexManage stand out from other vendors who offer migration services? “It’s the partnership,” Amy insisted. “Kris says, ‘We are here to be your partner. We are not here to be on top or offer you a service you can’t understand. We’re here to walk you through it.’ That was the best thing I ever heard. I have very few vendors I’ve worked with that are like that and that’s what makes FlexManage to me extremely good. They actually walked with us.”
As the project went on, Amy’s relationship with the FlexManage DCS team also blossomed. “Kris used to always tease me saying, ‘Anytime you want a job, you let me know,’” Amy remembered. The relationship continued as she moved higher in the organization, providing O365 services for the entire Time Warner family.
Then something unfortunate, yet fateful, happened. Amy was let go during a mass layoff at Time Warner (formally Turner) during February 2016. “The day I emailed out to Kris giving him his new contacts since I’d be leaving, Kris called me and he was just floored. I told him that I was ready for a new opportunity anyway and wanted to take some time to look – I have confidence in myself and I knew how employable I was. So he said that as soon as I’m ready, give him a call,” recalled Amy.
Four months later, she did indeed pick up the phone to call Kris. And he found the perfect role for Amy. She officially joined the FlexManage team in July of 2016 as a Solutions Architect for the DCS practice. Her first project was with a large financial services technology company and, during her first three months with FlexManage, Amy led the migration of 25,000 seats to the cloud. She hit the ground running.
What makes Amy such a perfect FlexManage fit is not only her genuine character, but her “mind for madness,” so to speak. “I can take chaos and put it into a plan of attack,” she said of herself. “I’m very good at deducting and analyzing. Fairly quickly, I can break through complexities and point out the fundamental issues behind what’s causing the problem and how we fix it.” If you ask anyone on her team, they will certainly vouch for her masterful analytical talents.
Today, after having been a part of the DCS team for nearly a year and a half, Amy swears by FlexManage’s skill in public folder migrations and Windows 10. But she thinks she has her finger on the DCS team’s true secret to success. “DCS is the whole package,” insisted Amy. “It’s about the leadership behind their role when they come into a company. I very much feel like we fuse with our customer. It’s never ‘that’s your job and this is my job.’ That genuine relationship with our client is the secret sauce. Then we lead, help guide and help our client understand it.”
But there is also something to be said about the cohesiveness of the DCS team itself. “I’ve always been impressed with the forward-thinking from FlexManage,” explained Amy. “Our communication is constant and we’re always talking about not only what is going on in a project, but where we are going forward.” Amy is so happy to be part of a team that can talk openly, stay on task, and just get the job done.
Looking back, it’s clear that Amy Westerman made the right choice when she came on board with our firm. “The reason why I came to FlexManage is because FlexManage stands for everything I want to represent,” said Amy, thoughtfully. As part of the DCS team, she feels like she has purpose. She feels like she is recognized and appreciated and inspired. She feels like an integral part of the FlexManage family. And let us assure you… she certainly is.
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Click here to view the original article on the FlexManage blog.
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