Job Description

Join Our Growing Sales Team at Checkwriters!

Are you outgoing, motivated, and ready to build a career in sales? At Checkwriters, you’ll have the opportunity to develop your skills, connect with businesses, and play an important role in growing our client base—all while being part of a vibrant, supportive team that’s redefining the payroll and HR experience.

We are a payroll and HR services software company focused on elevating every step of the customer experience. From interactions with our team to genuinely useful Payroll and HR software—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 we provide our customers with the best experience they’ve ever had with a payroll and HR provider.

What You’ll Do:

As a Business Development Representative at Checkwriters, you’ll be on the front lines of our growth efforts, creating new relationships and introducing prospective clients to Checkwriters. You will:

• Connect with prospective clients through high-volume outbound outreach, including approximately 80–100 calls per day and consistent email follow-up.
• Research prospective clients and engage them in thoughtful conversations to better understand their organizations and HR and payroll needs.
• Create a positive first impression of Checkwriters by providing a professional, helpful, and engaging experience with every interaction.
• Identify and qualify potential sales opportunities and coordinate next steps with our Account Executives.
• Build and maintain relationships with prospects through consistent and timely follow-up.
• Maintain accurate and detailed records of prospect interactions, activity, and next steps in HubSpot.
• Collaborate with our Sales and Marketing teams on campaigns, prospecting strategies, and other business development initiatives.
• Consistently meet and exceed individual activity and opportunity-generation goals.

Who You Are:

We’re looking for an energetic, persistent, and customer-focused professional who enjoys connecting with people and is motivated by goals. Our ideal candidate has:

• Strong written and verbal communication skills and the confidence to initiate conversations with new people.
• A customer-first mindset and a high level of professionalism.
• The motivation and persistence to succeed in a high-volume, goal-driven environment.
• Strong organization and follow-through, with the ability to manage a large volume of daily activity.
• The ability to listen, ask thoughtful questions, and build rapport with prospective clients.
• A willingness to learn, accept coaching, and continuously improve.
• Previous experience in sales, business development, customer service, or another customer-facing role is preferred, but not required.

Individuals from all career paths are encouraged to apply!

We offer a competitive salary and benefits package, company-sponsored social and community events, and an exceptional office workspace including sit-to-stand desks and private pickleball courts! This is an in-office position at our Northampton, MA location.

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