Job Description

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?

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