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50 Fastest Growing Companies of The Year 2017

“Our business strategy has been to empower our clients so that they can leverage their ERP and CRM systems to thrive and grow”: Crestwood Associates LLC


Crestwood Associates LLC was founded in the year 1998 and has office locations in Central and South Florida, Indiana, Michigan, Wisconsin and headquarters located in Mount Prospect, Illinois. 

Three factors are responsible for the company’s success

  • Hire and invest in people who want to make an impact
  • Empower clients to work without limits
  • Don’t be afraid to tear up the playbook and start over

Of these, hiring and investing in our people is the most critical. You can buy the same software we offer from lots of vendors, but you can’t find the same understanding of how these tools can power your business.

A chat with the leaders: Brian McGuckin and Timothy Thompson

Why was the company set up? How did you select the vertical and decide to be a part of the global platform?

The increasingly complex nature of business, from information to supply chain, makes it difficult for companies to identify and correct their course. This is especially true as you move into the smaller end of the SMB, where resources are limited and business moves at a much faster pace. We wanted to empower these firms with leading solutions, thoughtfully deployed.

How successful was your first project roll out?

Our first client is still our client, 18 years later. Part of our success was driven by implementing a great solution in regards to Dynamics GP that is ideally suited to meet the ERP needs of small and mid-market organizations. The other key aspect of our success was driven by the business objective to work closely with our clients to educate and empower them on Dynamics GP so they could be self-sufficient moving forward.

What challenges did you face in your initial years? What can your peers learn from it?

We learned early on that it is important for our team members to understand the “why” behind everything they do. Teaching our team to focus on the why allows them to question the status quo and continuously add value to the projects they undertake. In addition, everyone needs to take ownership of their actions and work in partnership with clients. We constantly ask ourselves, “Who owns this?” It’s become a mantra of sorts, and allows our employees to have skin in the game, ensuring our mutual success. My advice is to hone in on what truly makes someone a fit within your culture and develop a process to identify those traits. You’ll save a whole lot of time and energy by hiring right the first time.

If you have to list factors that have been/are the biggest asset to your organization, what would they be and why?

As a company we need to always be willing to ask if there is a better way to do something and be comfortable enough in our skin to redesign a business process. Great ideas can come from anyone within a business, so be open to them since the business owners are not always the only ones with answers.

That is the way that we want to work in our own organization, and we bring that freedom to our customers through education, process improvements, and decades of learning what works.

How big is your organization today? Briefly explain the organizational structure?

Crestwood has 75 team members spread across 13 states and 6 offices, so leveraging technology to stay connected is very important to our success. To that end, we invest in tools to keep our team connected, and we conduct all-hands video calls every other month. At the start of 2017, we split the company into product centric teams (i.e. Microsoft Dynamics 365, Acumatica, Microsoft Dynamics GP, etc.), each with a Practice Director responsible for the team’s success, in order to provide greater focus.

A short chronicle of the Ace dyad

Timothy Thompson, Partner: Tim has a unique career path that has provided him with a wealth of experience working with individuals and companies across the U.S. Tim graduated from the University of Notre Dame with a BA in Business Administration, Accountancy and began his career in the audit practice of Deloitte & Touche LLP. After earning his CPA in the State of Illinois, Tim left D&T to serve as a volunteer teacher on the Navajo Indian reservation in western New Mexico. After completing his teaching assignment, Tim attended Indiana University and received an MBA with a concentration in Small Business Development. Upon graduation, Tim joined the Entrepreneurial Consulting practice of Ernst & Young LLP and focused on delivering Lawson and PeopleSoft ERP solutions to the middle market.

Brian McGuckin, Partner:   Brian has a diverse background and brings a unique perspective and level of energy to Crestwood that has helped drive the organization to deliver excellence. After graduating from the University of Notre Dame with a BS in Mechanical Engineering, Brian was a nuclear submarine officer in the U.S. Navy. During his tenure in the Navy, he received a master equivalent degree in nuclear engineering and served on two submarines. While completing his final tour of duty, Brian attended the University of Chicago and received an MBA with concentrations in Finance and Accounting. After leaving the service, Brian joined the consulting firm of Ernst & Young LLP as a consultant in the Strategic Advisory Services practice. Brian’s focus at E&Y was in the development of valuation models, operating models, and strategic growth plans for Fortune 500 organizations.

“We provide the tools and quality services that help you perform above and beyond the competition.”