Expand Your Knowledge & Expertise

Get specialized training to master your role and opportunities to expand your horizons.

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Employee Benefits

Healthcare Plan

We offer a comprehensive, company-sponsored health care plan for health, dental, and vision. Features include a “Healthy Actions” incentive, gym/fitness reimbursement, an HRA, and FSA options to help with qualifying health and childcare expenses.

Paid Time Off

We like our employees to have a positive work-life balance, so we provide you with over two weeks of PTO during your first two years with us, and over four weeks of PTO after that. (Added bonus: you can roll your PTO into the next year for increased flexibility).


We invest in the knowledge and expertise of our employees, giving you opportunities for travel to industry conferences, events, and workshops. We want you to grow your career and network within the Payroll, HR, and tech world and we cover all travel costs to make that happen.

Work from Home + Flexible Schedules

Many of our positions offer work from home and flexible scheduling options. The expectation is that you’ll provide the best experience for our clients no matter where you’re located (but, we’ll note that many employees love coming into the office)!

Community Support

Our company and employees are very involved in community initiatives and events, often through our clients in the non-profit and education industries. Checkwriters sponsors several events throughout the year where employees are able to participate.

Great Company Atmosphere

Is the era of having a beautiful place to work over? We don’t think so! Our campus is a converted 19th-century school overlooking the New England city of Northampton, walking distance to parks, cafes, and restaurants. We place a high value on employee fitness opportunities with our private pickleball courts; host dining events throughout the year; and give our team opportunities to interact with their colleagues in other departments.

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Hear From Our Team

  • Dominique, Sales

    “I love working at Checkwriters because of the emphasis we place on client support. It makes my job really easy knowing my clients are in great hands.”

  • 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!”

  • Sam, Client Support

    “We’re a large company with a national presence, but with the most welcoming and personal culture! The environment at Checkwriters is one of a kind.”

  • 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.”

Seize Your Opportunities

View our currently open positions.