Northampton
Welcome to Northampton
Located in the Pioneer Valley of Western Massachusetts, Northampton was founded in 1654, was the home of 31st US President Calvin Coolidge, and is the home of Smith College and, of course, Checkwriters HQ! You’ll also find an array of restaurants, coffee shops, bars, art galleries, and museums all conveniently located in this walkable city right off of Interstate 91.
Location
Distance to:
Springfield 25m (19.3 mi)
Hartford 49m (44.6 mi)
Boston 1hr 45m (104 mi)
New York 3hr 15m (164.8 mi)
Checkwriters HQ Office Map
In October 2019, Checkwriters moved into a new, 40,000 square foot historic building in downtown Northampton. The building underwent a multi-year historic renovation and conversion to modern, high-tech office space to fit the requirements of a growing technology company.


Favorite Spots
Here are some of the preferred spots of the Checkwriters team:

Coffee Shops
- Dunkin' Damon Road Northampton
- The Roost
- Shelburne Falls Coffee Roasters
- Tart Baking Company
- Northampton Coffee

Restaurants
Special Projects
On the second floor along the Northwest side of the building is the Special Projects Department, which oversees a number of important client services and initiatives such as trainings and setup and implementation of our Onboarding and Benefits products.
Bridget Boisvert, Special Projects Manager
Tax
Along the Southwest corner of the second floor is the Tax Department, which oversees the filing of client taxes in all 50 states plus US territories, and has been recognized with the National Tax Partner of the Year award.
Jill Grasso, Tax Manager
Sales
On the East side of the building facing Round Hill Road is the Sales Department, complete with a soundproof "Zoom Room" equipped with the latest in video conferencing capabilities.
James LeDuc, Sales Manager
Conference and Training Center
The Conference and Training Center can accommodate large groups of up to 30 for meetings, trainings, webinars, and events. It is located off the main atrium.
Human Resources
On the East side of the building facing Round Hill Road is Human Resources, which oversees recruiting, hiring, compliance and engagement initiatives.
Carly Fallon, Director of Human Resources
Marketing
Past the Finance Department on the North side of the building, second floor is the Marketing Department, which dreams up creative ways of presenting Checkwriters' products to prospective customers across the country!
Dakota Hebert, Chief Marketing Officer
IT & Development
On the East side of the building facing Round Hill Road is the IT & Development Departments, where Checkwriters' infrastructure and security apparatus is managed and our software is designed and developed.
Stephen Sjostrom, Director, Software Development
Jonathan Flebotte, Director, IT Infrastructure
Packout
Located on the West side of the building is the Mail Room and Loading Dock.
Reception Area
Past the Café are the Reception area, Elevators, and Restrooms.
Finance
Walk up the stairs from the Reception area and immediately to your left will be the Finance Department.
Peg O'Grady, Chief Financial Officer
Operations
The large area on the South side of the second floor facing down Round Hill Road houses Checkwriters' Operations Department - where our Account Specialists and Team Leaders provide real-time responses to client inquiries and assist in the use of our Payroll and HR technology.
Nancy Liquori, Operations Manager
Benefits
The Benefits Department provides our clients with customized benefit packages and assists in the recommendation and implementation of benefits technology such as carrier connect and electronic employee enrollment. They also provide ongoing, year-long administrative support for clients who utilize Checkwriters Benefits Group as their benefits broker.
Implementation
Walk through the Banking and Marketing Departments on the second floor and you'll pass into the new, lofted addition to the original historic building. Here, you'll find an open common area with seating and meeting space, as well as the Conversions and Implementation Departments - tasked with onboarding new customers and ensuring their first experience with the Checkwriters Team is a positive one!
Sharon Glod, Implementation Manager | Tracy Fleming, Implementation Project Manager
Café
Enter through the main doors from the parking lot into the large, lofted atrium. Here, you'll find open seating for breakfast and lunch and the Café - complete with a coffee bar and espresso machine for you and your guests!
Executive Offices
James Hebert, Founder and President
Peg O’Grady, Chief Financial Officer
Pete Whelan, Executive Vice President
Keelie Hebert, Founder and Treasurer