Bill Checkosky
Title: Vice President, Commercial Lending, Greater Hartford Market Manager, Chelsea Groton Bank
Age: 48
Experience: 26 years
Believe it or not, Bill Checkosky got into the banking business because of regulation. When he was an undergrad at Bentley College, he penned a paper about the Depository Institution Deregulation and Monetary Control Act of 1980. That, plus a course on financial institutions’ operations, was enough to hook the analytical-minded history buff into a banking career that’s spanned more than 20 years and some of the biggest names in New England banking. Last fall, he joined Chelsea Groton Bank with the goal of expanding the bank’s commercial lending into the Greater Hartford market.
Q: Tell us about your day-to-day at Chelsea Groton Bank.
A: My day consists of calling on prospects, leveraging my network of COIs – attorneys, accountants, appraisers, other bankers and the real estate network – and attending as many Chamber events and networking events as possible. I’ve also been working very closely with the marketing department to coordinate on sponsorships and community involvement. Certainly, much of my time is also spent coordinating the deal flow in my pipeline for my customers and soon-to-be customers.
I also keep an eye out for movement in the banking industry and opportunity to add staff in Glastonbury, as well. A great place for a networking event was the CBIA economic update. It seems all of us all worked for Fleet at one point or another in our lives, and it was interesting to see all of my friends and former coworkers. I always keep an eye out as to what’s going on elsewhere. After 25 years, you know who the good, capable lenders are who can contribute to the future of Chelsea Groton Bank.
Q: You’ve been working in the Greater Hartford market for more than 25 years; when you think back on your career, what observations jump out at you about the market?
A: When I think about banking over the past 25 years, there are a few things stick out to me in Greater Hartford and in Connecticut and in banking in general.
We’ve seen consolidation, competition, certainly regulation and technology. There have been a significant number of mergers and acquisitions over the past 25 years. Personally for me, even back in my college days, I remember going to school in the Boston area, you had Shawmut, Fleet, Bank of Boston and Bay Bank. They’re all now one of the banks that make up Bank of America.
You’d think maybe with less banks, there’d be less competition, but it’s hypercompetitive these days, in particular in the Greater Hartford market – especially in small business area and in commercial real estate lending. I would say we all tend to chase the same companies and the same developers.
The regulatory environment and the increase in reporting requirements and compliance costs, that’s been substantial. I guess the end result is that we’ve all got, particularly in New England, stronger and better capitalized banks. The banks in Connecticut and in New England in general are much better capitalized than when I started.
In terms of what I’ve seen in lending, overall the basics of commercial lending really haven’t changed significantly whether it’s C&I or commercial real estate. Lending is lending.
The interesting thing about Greater Hartford, I’d say, is the variety, the talent, the highly educated workforce, just the general overall quality of the business community in this area. There are a lot of very smart, very talented people in Greater Hartford. Hartford in particularly has come a long way over the past 10 years. It’s much more dynamic and diverse than ever. When I was working in Hartford in the early ’90s, when I would get out of work at 5:30 or 6:00, it was a ghost town downtown. It’s much more dynamic now. Does Greater Hartford have challenges? Yeah, every community does, but I know a lot of people in the business community and I see this at many of the networking events I go to: people who love living and working in this area.
That’s what sticks out to me about Greater Hartford.
Q: What kind of companies have you been working with at Chelsea Groton?
A: I’ve been working with privately held, small to mid-sized businesses in various industries – fiber optics, several commercial property owners, manufacturers, contractors. Many of the small to mid-sized businesses, most of them are looking for basic things: working capital lines of credit, term loans for equipment or vehicles, commercial real estate mortgages, investment and owner occupied properties. We’ll do SBA loans and construction loans. We focus on opportunities up to about $10 million. We have the ability to hit larger transactions if we participate with other banks, but those are generally the kinds of businesses we’ve been working with at Chelsea Groton.
Q: What’s on your agenda for the rest of 2016?
A: What I’m looking forward to the most is developing and growing Chelsea Groton’s commercial presence and market share in Greater Hartford and beyond. We have 160-plus years of a very successful track record in New London County, and that track record is due to providing a superior experience to our clients. We plan to expand that successful track record in Greater Hartford, in addition to becoming a great partner to the overall business community.
Hopefully, this leads to opening a branch or two in the area and expanding the commercial lending staff.
Checkosky’s Top Five Golf Courses:
- Ellington Ridge Country Club
- Farm Neck Golf Club, Oaks Bluff, Massachusetts
- Fox Hopyard in East Haddam and its sister course, Crumpin Fox, in Bernardston, Massachusetts
- Hartford Golf Club in West Hartford
- Blackledge Country Club in Hebron





