jerry c

Get to Know: Jerry Calabrese at Cash Flow

We sat down with Jerry Calabrese, Business and Corporate Development Officer for Chesapeake Bank’s Cash Flow Division, so he could answer a few FAQs his clients ask about Cash Flow. We also got to know the guy behind the briefcase: from his family life and experience living outside of Philadelphia to his early career as an entrepreneur.

After all, it’s our employees at Cash Flow, and throughout all our divisions of business at Chesapeake Bank, that make everything we do possible.

Tell us a little bit about your role at Cash Flow.

Jerry Calabrese: I am a Business Development Officer for the Cash Flow Division of Chesapeake Bank. I am responsible for serving businesses in need of Accounts Receivable and Asset-Based Lines of Credit. I also work to develop referral relationships, oversee underwriting and negotiate pricing and deal structures for companies in need of cash flow. Although my general geographic area of business is the Northeast region, I do work with business customers throughout the entire United States.

CB: On a more personal note, tell us a little bit about your life outside of work.

JC: My wife Shari and I live about an hour north of Philadelphia and east of New York City, in an area called Bethlehem Township, Pennsylvania. Other than the brutal winters, it’s the perfect location to live, work and play. With just a short drive, we can enjoy the sights and sounds of large cities like Philadelphia and New York, be surrounded by picturesque mountains, or take a day trip to the beach.

I am the proud father of two daughters: Mikela and Nicole. My oldest, Mikela lives and works in Indianapolis and is a graduate of Indiana University. Nicole lives and works near home and obtained her undergraduate degree from the University of Pittsburgh and a master’s degree from Bryn Mawr College.

In what free time is available, I enjoy playing golf (not well, I’ll admit), and spending time with my family.

CB: What three questions are you asked most often?

JC: Being out in the field, I meet such a diverse group of business owners, but I find that many of them have similar questions. First and foremost, they want to feel secure that they are dealing with a reputable company. That’s one of my favorite questions, and it’s easy to answer. I simply state the facts: Chesapeake Bank is a 117-year-old FDIC-insured bank with strong growth, continuity of management and a team dedicated to both their customers and their communities.

Secondly, I’m asked about other services beyond the two primary products offered by Cash Flow, like financing options for commercial or residential real estate, auto, equipment, etc. Because I operate outside of Chesapeake Bank’s primary market (Virginia), I then explain that we can only offer our Cash Flow products or Merchant Services in states outside of Virginia.

Hardly an inquiry goes without questions related to cost and pricing. This is generally expected, as our customers are entrepreneurs who have risked it all to pursue their dream of starting a business. In past positions I’ve held, this question was somewhat daunting, as I knew it was coming and what my response would have to be. But, cost is an important part of the equation. Here at Cash Flow, we have unique risk underwriting which makes us priced perfectly to capture clients purely shopping for price, especially when compared to typical financing companies.

CB: What do you wish your customers knew about Cash Flow or its products and services?

JC: It can be difficult to convey two things that are generally abstract or secondary thoughts for our clients, but that I find most compelling. First, the importance of backend operations simply cannot be understated. While having a new client commit to working with us is gratifying and important, we keep our clients as a result of the quality and commitment of our operations staff, who are the best in the business.

Also, the entire team at Cash Flow is truly committed to seeing our clients’ businesses be successful. Unlike others in the financing business that may be interested in simply closing a sale, we are looking for the right companies, paired with the right price point, to provide great support and assist in reaching their growth goals.

CB: What’s in your tool bag that helps you do your job most effectively?

JC: I believe that my background as an entrepreneur for most of my professional life sets me apart from those that have been salespeople most of their careers. I have been on our clients’ side – stressing over being able to make payroll, health insurance coverages, the copier being jammed (or in my days the fax machine), worrying about who called in sick today and how to cover that loss.

It’s this unique perspective that gives me the ability to understand and have empathy for the plight of business owners.

CB: Do you have a favorite quote or motto?

JC: “The desire to win is not nearly as important as preparing to win.” — Bobby Knight

Connect with Jerry | LinkedIn | 610-442-9107 |

To learn more about Chesapeake Bank’s Cash Flow Division or contact us directly here.