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

Alex Herrera
Ryan Lorance

Account Management

Alex Herrera 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. Ryan is a graduate of Purdue University with a Bachelor of Science in management. Alex earned her Bachelor of Arts degree in Music Business Management from Columbia Chicago.

Jay Ebey

Robert Jones and Leo Marquez are our account coordinators. They are involved with calling and email distribution. From gathering content through monitoring writing, design and programming, emails are a time intensive process. Continual evaluation of open rates and clickthroughs assures that emails are distributed at the best time and day to maximize exposure. Robert is a graduate of the University at Albany, State University of New York with a Bachelor's degree in Business Administration. Leo received his Bachelor's degree in Media and Cinema Studies from the University of Illinois at Urbana-Champaign.

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.



Shedreonna Ashley 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 a Bachelor of Science degree in psychology from Columbus State University.

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.

Our Call Center

Winsby Callers are the perfect combination of friendly, inquisitive and persistent. For list verification they are finding the best people to approach about our clients' products and services. For customer satisfaction surveys they are getting people to take a few minutes to give valuable feedback about how well our clients performed.

Michelle Buker

Michelle Buker is working toward her BAS in criminal justice. She also investigates cold cases for missing persons.

Lisa Melnick

Lisa Melnick has two sons, and one granddaughter. She was a court stenographer for 17 years, then worked at Starbucks for ten years.

Terri Nooner

Terri Nooner is a lifelong Chicago native. She enjoys reading and spending time with family.

Jake Tallon

Jake Tallon has worked at Winsby since 2018 and earned a bachelor's degree in film from Columbia College in Chicago.

Brian Van Dyke

Brian Van Dyke has tested and called all types of projects. He has trained over 60 Winsby callers and has been with Winsby since 2015.

Brian Van Dyke

Jessica Townsend has three children and is the co-owner of a home services company with her husband. She is in the process of becoming a Notary.

Brian Van Dyke

Nia Chanel is working towards her BA in Arts, Media, and Entertainment. During her free time she creates music and travels across the country to attend music festivals.

Brian Van Dyke

Jennifer Eades earned her associates degree in Liberal Arts with a major in cognitive psychology and ethics. She enjoys outdoor activities and is a lifelong Cubs fan. She has three dogs and adores animals.

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