Leadership Team

Paul Chaffee, CEO/CFO

A passionate advocate for technology and innovation in education, Paul has dedicated the vast majority of his career to providing technology services and solutions to schools.  Under his leadership as CEO/CFO and co-founder of Software Answers, Inc., the company grew from a technology consulting start-up in 1994 to a leading provider of K-12 software solutions.  Today he oversees the direction of ProgressBook Suite, a software solution dedicated to the K-12 education industry.  Prior to Software Answers, Paul spent ten years with Digital Equipment Corporation (DEC) as a consultant where he lead the implementation of a Student Information System into a major metropolitan school district in Ohio.  The final solution helped the school district streamline processes, cut costs, and improve  the overall quality and accessibility of the students’ data.  Paul is an active member of Northeast Ohio’s business and technology community. He is currently a board member for OHTec, (formerly known as NEOSA), a committee member for the COSE strategic planning course, and a member of the COSE Advocacy committee. 

Scott B. Miller, COO

A co-founder of Software Answers, Inc., Scott Miller serves as the company’s Chief Business Development Officer.  With more than 25 years’ experience in K-12 education, Scott brings a wealth of industry knowledge and market expertise to the organization. His responsibilities include overseeing research and new business development as well as finding opportunities for partnerships in the marketplace. Prior to the company’s startup, Scott worked at Digital Equipment Corporation (DEC), and Pentamation where he provided technology and consulting services to such organizations as Cleveland City Schools, NASA Lewis Research Center, EverReady Battery Co. and Pioneer Standard Electronics.  He is currently an active member of the Cleveland Entrepreneurs Organization (EO), an association that helps business owners learn and grow from each other.  

Christopher L. Aiello, Director of IT and Quality

As Director of IT, Product Quality and Customer Support, Christopher oversees the teams responsible for providing stable systems for staff and customers, ensuring product quality, and delivering knowledgeable service and support to our customers.  A veteran of Software Answers’ management team, he joined the company in 1995 and has risen through the ranks to assume responsibility for overall planning, organizing and execution of technology functions.  Under his direction, the company recently launched a faster, more reliable and affordable hosting solution in partnership with the Management Council of the Ohio Education Computer Network (MCOECN). Before joining Software Answers, Christopher held IT leadership positions at Deloitte Consulting, Factory Controls and the U.S. Census Bureau. 

Steve Reeling
Steve Reeling, VP of Product, Sales and Marketing

Steve brings more than 22 years of technology and product development experience to his role as Vice President of Product, Sales and Marketing.  He is responsible for providing overall product management leadership to the ProgressBook Suite as well as overseeing sales and marketing functions to maximize business opportunities and revenue.  Steve joined the company in 2012 as StudentInformation Product Manager, and has been instrumental at working with the solution’s funders – the Ohio Educational Computer Network (OECN) and its network of Information Technology Centers (ITCs) – to drive a customer and market-focused product sales system.  Prior to joining Software Answers, Steve worked at a number of technology companies, including OEConnection, where he served as Product Manager for their automotive parts supply chain technology.

Rob Sweeney, Customer Support Manager

As Software Answers’ Customer Support Manager, Rob is committed to ensuring that ProgressBook customers receive quality technical support in a timely manner.  He is responsible for the day-to-day operations of customer training and support, product implementation and rollout, technical installations and upgrades, and product documentation. Under Rob’s leadership, the company’s help desk operation boasts a response and resolution customer satisfaction rating of 98%.  Before joining Software Answers’ Customer Support team in 2007, he worked as a technical support/quality analyst for AMS Services/Rackley Inc., a provider of software for home, auto and commercial insurance. 

Craig Munyon, Product Manager

As a Product Manager at Software Answers since 2013, Craig has been instrumental in leading the development and direction of ProgressBook SpecialServices solution as well as State Reporting with StudentInformation.  Having previously served as Quality Assurance Analyst on the StudentInformation and GradeBook teams for five years, Craig brings in-depth product knowledge and technical expertise to his leadership role. Craig joined Software Answers in in 2005 as a Customer Support Specialist.

Cindy Chaffee, Human Resources and Finance Manager

A former RN at a busy teaching hospital, Cindy approaches her role as Human Resources and Finance Manager with patience, empathy, and attention to detail.  Since joining the company in 1995, she has assumed responsibility for the administration and coordination of human resources functions, as well as financial planning, business and payroll processes.  Under her direction, Software Answers has become recognized as an employer of choice, receiving numerous awards for creating an employee-friendly work environment that promotes innovation, engagement and achievement.  As a proud supporter of her local public school district, Cindy has served the Nordonia Hills School district as a volunteer, committee member and PTA board member. Prior to Software Answers, Cindy worked as a Nurse at University Hospitals of Cleveland and a Staff Development Coordinator at the Hattie Larlham Foundation 


6770 West Snowville Road Suite 200
Brecksville, OH 44141
Tel: (440) 526-0095
Fax: (440) 526-2557
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