We're investing in technology and AI to make our service even better, and we're looking for someone to help lead the way! 

Checkwriters has provided payroll and HR services to employers since 1989. We're headquartered in Northampton, Massachusetts, and known for something rare in our industry: a team that's responsive, knowledgeable, and get clients accurate answers so payroll is done right. 

As our AI Solutions Engineer, you'll have the opportunity to identify and build ways to supercharge our people so they can continue to deliver a premium service experience. You'll design and develop internal tools, automations, and AI-driven solutions that help our Sales, Onboarding, Support, and Client teams work more efficiently and effectively. Working across the entire client journey, from the first sales conversation to long-term client relationships, you'll collaborate with teams throughout the company and work closely with our technology leadership to identify opportunities, solve challenges, and bring innovative ideas to life. This is a hands-on role with plenty of room for creativity, innovation, and the opportunity to make a meaningful impact on how we work and serve our clients.

This is an in-office position at our Northampton, Massachusetts location.

What You'll Work On:

• Sales intelligence: research, data enrichment, and tools that help our sales team prepare
• Client onboarding: smoother, faster experiences for new clients
• Client experience: tools that help our client teams stay responsive and proactive
• Reporting and insights: dashboards and analysis that help leaders make better decisions
• RevOps: keeping our CRM and data clean, connected, and useful
• AI agents: design and deploy Claude-based agents that do GTM work on their own
• AI exploration: testing new tools and bringing the best ideas to the team

Our Ideal Candidate Will Have:

• 3+ years of experience in Revenue Operations, Sales Operations, Sales Engineering, or a similar technical or customer-facing role. Relevant entrepreneurial or independent project experience will also be considered.

• Demonstrated ability to develop and implement technical solutions, automations, or tools that improve business processes and efficiency.

• Strong familiarity with emerging AI technologies, tools, and applications, with the ability to identify practical business use cases.

• Working knowledge of Python or JavaScript, SQL, APIs, webhooks, and AI-assisted development tools.

• Strong communication and interpersonal skills, with the ability to collaborate across departments and explain technical concepts to nontechnical audiences.

• Proactive, solutions-oriented mindset with the ability to identify opportunities for process improvement and independently execute solutions.

• Strong commitment to data security, confidentiality, and responsible handling of sensitive client information.

Interested candidates: Please submit a resume with links to 2-3 things you've built, such as GitHub repo, a demo video, or a live tool.