We help you grow

Winsby has worked with businesses all across the world to help them grow, using proven processes that are constantly monitored to make sure the results are consistently good. We drive growth by growing your prospect list, pushing your customers to purchase more often with more variety, then monitoring your customers' interactions with your company to make sure there aren't any issues that you aren't aware of.

Impressive results

Our clients grow consistently, and they retain their customers, so the growth has a positive impact on their businesses. We often find problems you didn't realize you had, but once you know about them, it's easy to fix them.

The problems we run into are those that follow growth—there's more hiring, and procedures sometimes change with more volume. We're based in Chicago, but we have clients across the U.S. Many of them are global. Their success is our report card, and we are obsessed with our high GPA.

We have experience with companies in a wide variety of businesses:




Service Businesses

Service Businesses

Our Founders

In 2003, Steve Clegg and Debbie Frakes founded Winsby Inc. They had both been involved with a variety of businesses and had developed predictable ways of generating growth. They wanted to share their knowledge and experience with other companies to help them minimize problems in figuring out the best ways to grow.

Steve Clegg

Steve Clegg

Steve had been with AEA Investors, Inc. and had served on the boards of directors and in executive positions for companies they purchased. The industries were diverse and included a group of steel mills that were bought individually, then combined, a chain of discount retail stores across the U.S., a roofing materials manufacturer that expanded into installation, a weight loss franchise that grew to over 2,000 locations in North America, a group of shoe stores that tripled, a company that produced specialty items according to customer specifications across several locations with disparate capabilities, and more!

Initially, he began his career in international finance, working for WR Grace, then Avis. He received a Bachelor of Science from the United States Air Force Academy and a Master of Business Administration from the University of Chicago.

Debbie Frakes

Debbie Frakes

Debbie has started several businesses, and each has grown rapidly. With her first venture, she purchased a service franchise that expanded to seven locations within two years. Another startup established an elder care management company throughout a major metropolitan area. A successful catalog operation and a market research company also preceded Winsby.

Her first position outside of school was as an environmental consultant in New York City. She earned a Bachelor of Arts in environmental science from Barnard College, Columbia University, and a Master of Business Administration in finance and marketing from the Columbia University School of Business.

Winsby Departments

Jessica Findley
Ryan Lorance

Account Management

Jessica Findley and Ryan Lorance are our senior account managers. They are charged with ensuring that all services are completed on time and on task for Winsby clients. They oversee a staff of account managers who support their efforts admirably. Jessica is a graduate of Illinois State University with a Bachelor of Science in marketing, and Ryan earned a Bachelor of Science in management from Purdue University.

Jonah Everett

Jonah Everett is our account coordinator. He specializes in coordinating the process for distributing emails, from gathering content through monitoring writing, design and programming. Continual evaluation of open rates and clickthroughs assure emails are distributed at the best time and day to maximize exposure. Jonah earned his Bachelor of Science in Marketing from the Indiana University Bloomington.

Eric Druhan


Overseeing our design department is Eric Druhan, the keeper of Winsby's high standards, to ensure that all projects are creative, intelligent, and clearly communicated. He graduated from Indiana University Bloomington with a Bachelor of Fine Arts in graphic design.

Gerard Gerace

Gerard Gerace is an essential part of the design team. He and Eric collaborate and brainstorm to make any idea at least twice as amazing. A graduate of the University of Dayton, Gerard earned his Bachelor of Fine Arts in visual communication design.

Alex Herrera


Alex Herrera leads the research and proofreading department to provide information to the writers. Then, it's all double checked and proofed at each step of the process, from writing to design to programming. She earned her Bachelor of Arts degree in Music Business Management from Columbia Chicago.

Ryan Miller


Ryan Miller is our master writer. He can make anything sound amazing by crafting a message carefully and eloquently. A graduate of the University of Michigan, Ryan earned his Bachelor of Arts degrees in German and political science.

Sidharth Malhotra

Lists and Analytics

Sidharth Malhotra has a staff of analysts and data managers to handle projects that range from cleaning lists to programming analytics functions that reveal patterns in our invoice data. He earned his Bachelor of Technology Computer Science from PTU, Jalandhar and his Master's in IT Business Management (MBA-IT) from Symbiosis University, Pune, India.

Ask a Question