Demo

Sales Support Specialist

Checkwriters
Northampton, MA Full Time
POSTED ON 1/6/2026
AVAILABLE BEFORE 2/4/2026
We’re looking for a go-to teammate who keeps our Sales Team shining and our clients raving. In the Sales Support Specialist role, you’ll join prospect calls, run demos, create proposals, and help new clients feel at home; making first impressions turn into lasting partnerships.

Checkwriters is a payroll and HR services company focused on elevating every step of the customer experience. From customer interactions with our team to our genuinely useful software that's designed to fit customer needs — we don’t just provide an excellent product. We have a team of experts who care about the details, and work continuously to ensure that the customer experience is the best of any payroll and HR provider.

What you’ll be doing:

  • Partner with our Sales Team on calls, presentations, and proposals that wow.
  • Be the bridge between clients, Sales, and our internal experts.
  • Dig into data and trends to spot opportunities and improvements.
  • Keep communication flowing, no prospect or client slips through the cracks!
  • Potentially join Account Executives at trade shows, conferences, and networking events.
  • This role may also include following up with clients post-sale to ensure satisfaction and keeping them informed about new features and services.

What makes you our ideal fit:

  • Experience in sales, customer service, or admin. (Bonus if you know HR/payroll!)
  • Knowledge of HRIS platforms and payroll systems (preferred but not required).
  • Top-notch communication skills, written and spoken.
  • Strong presentation skills.
  • Organization superpowers and the ability to juggle multiple priorities.
  • CRM experience (HubSpot = extra points).
  • A team player who’s also confident flying solo.
  • A positive attitude, a strong work ethic, and a drive to make an impact.

At Checkwriters, we’re not just hiring for a job, we’re building a team of rockstars who love helping clients and each other succeed. Could that be you?

Salary : $50,000 - $70,000

If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Sales Support Specialist?

Sign up to receive alerts about other jobs on the Sales Support Specialist career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$69,294 - $90,454
Income Estimation: 
$84,489 - $116,961
Income Estimation: 
$88,480 - $114,350
Income Estimation: 
$95,613 - $132,947
Income Estimation: 
$69,294 - $90,454
Income Estimation: 
$84,489 - $116,961
Income Estimation: 
$88,480 - $114,350
Income Estimation: 
$95,613 - $132,947
Income Estimation: 
$48,269 - $61,450
Income Estimation: 
$79,910 - $123,078
Income Estimation: 
$54,802 - $70,174
Income Estimation: 
$54,802 - $70,174
Income Estimation: 
$79,910 - $123,078
Income Estimation: 
$72,620 - $101,287
Income Estimation: 
$88,480 - $114,350
Income Estimation: 
$79,910 - $123,078
Income Estimation: 
$116,558 - $154,666
Income Estimation: 
$116,001 - $149,277

Sign up to receive alerts about other jobs with skills like those required for the Sales Support Specialist.

Click the checkbox next to the jobs that you are interested in.

  • Account Management Skill

    • Income Estimation: $49,505 - $67,506
    • Income Estimation: $57,456 - $77,960
  • Customer Acquisition Skill

    • Income Estimation: $43,501 - $61,493
    • Income Estimation: $46,546 - $65,526
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Checkwriters

  • Checkwriters Northampton, MA
  • Join Our Growing Sales Team at Checkwriters! Are you a motivated, results-driven sales professional ready to take the next big step in your career? At Chec... more
  • 4 Days Ago


Not the job you're looking for? Here are some other Sales Support Specialist jobs in the Northampton, MA area that may be a better fit.

  • Clinical & Support Options, Inc. Springfield, MA
  • CSO is looking for a Cleaning Specialist to join our Facilities team in Northampton. Starting salary: $31,000-$35,000/year You Will As a Cleaning Specialis... more
  • 4 Days Ago

  • Clinical & Support Options, Inc. Greenfield, MA
  • CSO is looking for a Cleaning Specialist to join our Facilities team in Greenfield. Starting salary: $31,000-$35,000/year You Will As a Cleaning Specialist... more
  • 3 Days Ago

AI Assistant is available now!

Feel free to start your new journey!