About Us – Checkwriters

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Hear From Our Team

Mike, Client Success

“Everyone is kind, knowledgeable, and helpful – you will learn and grow more every day with the support of an awesome team.”
Lukasz, Finance

“There’s a family atmosphere throughout the office and everyone genuinely cares about their colleagues. The private pickleball courts aren’t so bad either!”
Louise, Client Support

“I really enjoy working at Checkwriters for the same reason that I was attracted to seek employment here. It’s the shared belief that the employee is the company’s greatest asset – which in turn helps make our clients the HR and Payroll heroes at their own organizations.”
Dakota, Chief Marketing Officer

Leadership

Jim Hebert

Founder and CEO

Jim Hebert

Founder and CEO

In 1989, Jim took a chance on the burgeoning industry of payroll and tax services, which at that time was a paper-based endeavor focused exclusively on the processing of client payrolls and their timely physical delivery. Over the years, he oversaw the building of a Software Development team which led to the launch of the Checkwriters platform. Three decades later, the organization he founded is a national player in the field of Human Resources technology, which delivers an online platform and hands-on, accessible service to thousands of clients across the United States.

Prior to founding Checkwriters, Jim served as a non-commissioned officer in the U.S. military, 82nd Airborne from 1981-1985.

Margaret O’Grady

Chief Financial Officer

Margaret O’Grady

Chief Financial Officer

Peg joined Checkwriters in 1997 and has spent the years since recruiting and developing a strong and highly skilled Finance Department as Chief Financial Officer for Checkwriters and its affiliates.

A graduate of Western New England College, Peg spent 12 years in public accounting before joining Checkwriters. She has been a Certified Public Accountant (CPA) since 1987 and is a member of both the American Institute of Certified Public Accountants (AICPA) and the Massachusetts Society of Certified Public Accountants (MSCPA).

Outside of work, Peg is a mother and grandmother. She enjoys traveling, especially to warm destinations, and exploring wineries and breweries throughout New England and beyond.

Steve Sjostrom

Development Program Manager

Steve Sjostrom

Development Program Manager

Steve joined Checkwriters in 2008 and has been instrumental in shaping the technology that powers the Checkwriters platform. As a key architect of the system, he has led the development team in building a modern, scalable solution while overseeing the delivery of hundreds of enhancements, features, and services across the Checkwriters platform.

In his current role as Development Program Manager, Steve continues to guide the evolution of the platform while supporting our in-house development team. He is a Certified Scrum Product Owner (CSPO) and Certified Scrum Master (CSM).

Nancy Liquori

Director of Training & Development

Nancy Liquori

Director of Training & Development

Nancy has dedicated her career to building high-performing customer service teams and creating exceptional client experiences. Since joining Checkwriters in 2003, she has played an integral role in the company’s growth and success. Beginning as Operations Manager and advancing into her current role, Nancy focuses on training and developing team members and ensuring employees have the knowledge, resources, and support needed to deliver outstanding service to our clients. Her commitment to continuous improvement helps drive the exceptional client experience that Checkwriters is known for.

Sharon Glod

Director of Client Conversions

Sharon Glod

Director of Client Conversions

Sharon joined Checkwriters in 2008 in the Tax Department before quickly expanding her role to lead payroll conversions and help build the foundation of the company’s Implementation Team. Her leadership and dedication led to her promotion to Implementation Manager in 2015.

Today, as Director of Client Conversions, Sharon oversees the team responsible for setting up new client accounts and ensuring company and employee data is transitioned to Checkwriters accurately and efficiently. Sharon is a Certified Payroll Professional (CPP), and is committed to delivering a seamless onboarding experience and helping clients start their partnership with Checkwriters on the right foot.

Tracy Fleming

Director of Client Success

Tracy Fleming

Director of Client Success

Tracy joined Checkwriters in 2012 following a successful career in the banking industry, where that industry knowledge made her an excellent addition to Checkwriters’ leadership. In her role as Director of Client Success, Tracy works with her team to ensure each client receives exceptional support from kick-off to go-live, and that they continue to have access to professional and knowledgeable service and resources throughout their time as a Checkwriters client.

Tracy is a proud mother of two, but also a lover of shoes, hiking, kayaking, gardening, and attending concerts with her husband.

James LeDuc

Director of Sales

James LeDuc

Director of Sales

James joined Checkwriters in 2014 as a Senior Sales Account Executive. His success in building teams and developing new sales talent led to his position as Director of Sales.

Through his prior industry experience, James saw how the one-size-fits-all approach to Payroll and HR software and services could be drastically improved. This informs both his leadership of the Checkwriters’ national Sales Team and in his presentation of creative payroll, attendance, and human resource solutions for new and prospective clients.

Meghan Mancino

Tax Manager

Meghan Mancino

Tax Manager

Meghan joined Checkwriters in 2017 as a Tax Specialist and currently serves as the Tax Manager. As Tax Manager, she is responsible for the Tax Department’s timely filing of payroll tax returns and remittance of tax payments to the IRS, and oversees the department’s tax responsibilities on behalf of Checkwriters clients in all 50 states plus the Virgin Islands and Puerto Rico. In addition, her department is responsible for the processing and distribution of W-2s, submittal of amended tax returns and corrected W-2s, and ensuring new taxes, such as Paid Family and Medical Leave, are added to clients when applicable by state.

Before joining Checkwriters, she worked in human resources, primarily with payroll and benefits and employee onboarding. Meghan is Fundamental Payroll Certification (FPC)-certified through the American Payroll Association (APA).

Dakota James Hebert

Executive Vice President

Dakota James Hebert

Executive Vice President

Dakota joined Checkwriters in 2013, where he worked in the Sales and Marketing departments and currently serves as Executive Vice President.

Before joining Checkwriters, he worked in communications in the U.S. Senate in Washington, D.C. He lives with his wife and children in Massachusetts.

Samantha Hathaway

Technical Solutions Manager

Samantha Hathaway

Technical Solutions Manager

Sam joined Checkwriters in 2019, as a Client Support Specialist and has advanced through several roles, including Client Support Manager, and now serves as a Technical Solutions Manager. In her current role, she acts as a key liaison between the Development and Client-Facing teams, helping translate client needs into innovative solutions while ensuring new product enhancements deliver meaningful value to customers.

Before joining Checkwriters, Sam oversaw payroll operations for a family-owned business. A Florida native, she now calls Massachusetts home, where she lives with her husband and their dogs.

Megan Butz

General Counsel

Megan Butz

General Counsel

Megan joined Checkwriters in 2020 and is responsible for reviewing, revising, and implementing internal policies of the company, advising on human resource, employment, and labor matters, and monitoring and publishing state and federal legal updates to the Checkwriters News and Compliance Center for distribution to thousands of clients around the country.

Before joining Checkwriters, Megan served as a judicial law clerk for the justices of the Massachusetts Probate and Family Court performing legal research and writing, followed by private practice in Cape Cod. She lives with her husband and children in South Carolina.

Felicia Corbeil

Human Resources Manager

Felicia Corbeil

Human Resources Manager

Felicia joined Checkwriters in 2020, where she serves as the Human Resources Manager. Her particular areas of focus include hiring, benefits administration, and the development and implementation of company policies in conjunction with the Checkwriters Compliance Team. She is a member of both our ACA Team and ERC Team where she assists clients on the intricacies of those programs, requirements, and filings.

Felicia holds a Masters in Business Administration and is based in Massachusetts, where she lives with her husband and children.

Youssef Karami

Director of IT Infrastructure

Youssef Karami

Director of IT Infrastructure

Youssef joined Checkwriters in 2021 as the Director of IT Infrastructure. Since joining the team he has provided his expertise in the design, implementation, operation, and management of the company’s on-premise and cloud IT infrastructure as well as implementing permanent solutions to ease and improve the day-to-day operations within the organization.

Youssef brings 15 years of experience in the field of information technology. He is Cisco-certified in network administration and has worked in various industries including the medical, biotech, and IT sectors.

Kevin Gregory

Engineering Director

Kevin Gregory

Engineering Director

Kevin joined Checkwriters in 2022 as a Software Engineer and now serves as Engineering Director.

With more than 15 years of experience in software development, he has played a key role in enhancing and expanding the Checkwriters platform. His diverse background spans digital marketing, healthcare, education, financial services, and utilities, bringing a broad perspective to the development of innovative solutions that support both clients and employees.

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