Based in Portland, Maine, MyHealthMath provides health insurance
decision support and optimization to organizations across the country.

At MyHealthMath, we believe that quality inputs can lead to powerful results. That’s why we’ve developed an integrated, data-driven solution that combines predictive modeling with a unique personalized approach – so we can arm you with the numbers you need to make an informed decision.

Employers and employees across the country rely on MyHealthMath to gain strategic control, obtain invaluable insight into the cost and value of their benefits, and yield extraordinary savings.

Bob Watterson

Founder / CEO

Bob Watterson is an entrepreneur with a sales and management background in financial services and technology. After graduating from Dartmouth College, he began his career at Procter & Gamble in their sales management training program.

He moved into financial services and founded First Financial, a residential mortgage company. There he conceived and created FirstFacts, one of the mortgage industry's first Decision Support tools, to help consumers navigate the myriad of loan choices.

MyHealthMath uses a similar approach, combining consumer interviews with proprietary algorithms to help employees and their employers understand optimal health plan choices for their unique circumstances.

Tobey Scott


Tobey Scott has had a long tenure in software development, applications, and systems starting with early computer graphics systems (pre-Mac, pre-IBM PC) through cloud/virtual computing architectures and implementations.  

For over two decades he owned and operated a Microsoft Gold Certified Partner organization specializing in Microsoft Dynamics and various middle market ERP systems. He has designed, developed and implemented multiple systems involved in Medicare billing, third party insurance administration, pharmaceutical operations, financial modeling, forecasting, and data analysis.  

At MyHealthMath he is pursuing his passion to develop methods and systems that allow rational decision-making in an increasingly complex dynamic world.  

Brendan Canning

VP of Business Development

Brendan Canning has been in the benefits industry for over 25 years and has held sales roles at multiple insurance carriers. Brendan came to MyHealthMath after working at Metlife for 15 years, first as an Account Executive in San Francisco and then in an executive role as National Sales Director. At Metlife, he was responsible for specialty markets, which focused on multiple employer entities such as associations, trusts, and professional employer organizations (PEOs).

Brendan’s experience gives him unique insight into the different distribution avenues of insurance products and services through carriers, brokers, TPAs, benefits administration platforms, and enrollment firms.

Rebecca Taylor

Director of Health Data Analytics

Rebecca Taylor received her medical training at the University of Pittsburgh School of Medicine, where she pursued a dual degree in medicine and public health. As a National Institutes of Health Research Fellow, she became passionate about the pursuit of better health outcomes through the convergence of health care, technology, and behavioral economics. 

At MyHealthMath, Rebecca is responsible for integrating medical expertise and health behavior knowledge to ground our process in a foundation of cutting-edge research and insight. She leads data mining efforts to glean behavioral insights that will improve patient health, empower employees, and create more efficient and responsive health systems. 


NeoNet Capital

NeoNet Capital invests in out-of-the-box, innovative solutions for IT, alternative energy, specialized materials, telecom, and fin-tech. We are particularly interested in early stage companies with bright and passionate entrepreneurs addressing the global market.

Maine Technology Institute

The Maine Technology Institute (MTI) is an industry-led, publicly-funded, nonprofit corporation that offers early-stage capital to Maine-based businesses. MTI’s core mission is to diversify and grow Maine’s economy by encouraging, promoting, stimulating, and supporting the innovation of new products, services, and companies – thereby creating and retaining quality jobs in Maine.