Meet the Psympl Team

Meet the Psympl Team is a series published under Psympl Answers in which a member of the Psympl team is highlighted to get to know them better and understand them on a more personal level. The series follows a Question & Answer format, much like an interview.

This edition of Meet the Psympl Team features Ken Riley, the VP of Customer Success of Psympl, Inc. 

What is your background? How did you get your start?

My career has been a "bits and bytes" evolution, starting from the ground up as a network engineer and scaling the heights of healthcare IT leadership for over 20 years. I was born in Okinawa, Japan, and raised as a "military brat," traveling the world with my father, a C5 pilot. This life on the move forced me to learn how to become fast friends with people from all walks of life, sharpening the interpersonal skills that are now the cornerstone of my approach to customer success.

That focus and drive led me to join the military as soon as possible at age 17, eventually serving as a Staff Sergeant in a Communications Unit. My service took me to the Middle East, including Kuwait and Riyadh, where I managed critical communication infrastructure under high-pressure conditions. Whether troubleshooting telephone equipment in a combat zone or leading IT for a $2.1B health system, I have always been defined by a mission-first mindset and a commitment to detailed execution.

I learned the healthcare business from within the "bricks and mortar" of the UMass health system and the Baystate Health system, eventually serving as CIO for one of their community hospitals. As the Director of Patient and Population Health Technologies, I managed extensive portfolios including the local Health Information Exchange, the Salesforce CRM, and mobile applications to learn and apply my skills on engagement outside in the community. My work on the "digital front door" ensured that patient portal implementations optimized the connection between complex technical systems and human needs.

Why did you join Psympl®?

I joined Psympl® because of my deep history with the core science behind this company, having worked with the original team that developed this psychosegmentation model. I witnessed firsthand how understanding a consumer’s "why"—their motivations and communication preferences—could revolutionize engagement. The model was incredibly successful in healthcare, achieving 91.1% accuracy in identifying profiles to motivate real behavioral change.

During my doctoral research, I used this model to assess the "digital front door" through Natural Language Processing of patient messaging. I explored how the digitization of the human experience creates tailored opportunities for engagement at the very first point of contact. This research confirmed that segmenting populations based on attitudes and lifestyles is the key to moving beyond "one-size-fits-all" approaches to achieve superior outcomes.

Psympl® provides the opportunity to take this proven, life-changing concept and apply it to new, highly regulated industries like financial services. I am excited to work with an established team that moves beyond basic demographics to engage with the actual psychology of the consumer. It is a chance to operationalize a concept I have studied and practiced for years, ensuring it becomes the standard for how institutions build trust at scale.

What is your current role and responsibilities?

As the VP of Customer Success, I lead the strategy to own and scale enterprise outcomes for Psympl®. My mission is to ensure our Psychographic AI™ is a growth engine that delivers measurable value, retention, and expansion within complex, regulated organizations. I serve as the primary steward of our long-term relationships, connecting your strategic business goals with our platform’s unique capabilities.

I operate at the intersection of product, data science, and revenue to design structured onboarding and success strategies. By defining clear success plans and KPIs, I ensure every account sees the operational impact of our behavioral insights. My goal is to reduce time-to-value while maintaining the enterprise rigor required by banks, wealth managers, and financial entities.

Ultimately, I am the internal voice of the customer, translating real-world feedback into actionable recommendations for our product roadmap. I bring a veteran's discipline, a CIO's perspective, and over 10 years of experience as a Trustee and Board Member for Country Bank to this role. Serving on Country Bank's Risk and Audit committees as a technology advisor gives me a unique "board-level" understanding of the compliance and security needs of our financial services clients.

What motivates you in your work?

At my core, I am a problem solver who thrives on creating experiences that make outreach and engagement truly effective. I believe the "why" behind human behavior is the most important piece of data we can possess. My motivation is to use our platform to humanize digital interactions, ensuring that technology serves as a bridge rather than a barrier to human connection.

I find immense satisfaction in translating complex technology into tangible business outcomes, such as engagement lift and operational efficiency. I enjoy the process of defining success plans and then relentlessly executing against those goals to exceed expectations. For me, work is about proving that data-driven platforms can lead to better real-world results for both the business and the end-user.

Collaboration is another key driver for me, as I naturally operate across functions to bridge the gap between data science, marketing, and client stakeholders. Building and mentoring a team that is passionate about customer outcomes is a core part of my professional mission. I am motivated by the challenge of building structure where none exists and ensuring Psympl® remains a transformative partner for our clients.

What are your interests outside work?

When I am not deep in the world of Psychographic AI™, I am often pushing my physical and mental limits as an Ironman Triathlete. Training for these grueling challenges requires a level of discipline and endurance that mirrors my professional life. I believe that pushing your comfort levels to the absolute limit—whether on a racecourse or in a boardroom—is the only way to achieve true growth.

Family is the center of my world; I am a devoted husband and father to three children. They are my primary motivation and the reason I value the "human" element in everything I do. Balancing the rigors of an executive career with being a present father and husband keeps me grounded and provides the ultimate perspective on what "success" truly looks like.

I am also a world traveler who has reached the Kilimanjaro Summit and participated in the Pan-Mass Challenge. My travels throughout the Middle East and my upbringing in Japan have given me the energy to tackle complex problems with a global perspective. These experiences remind me that behind every data point is a person with their own goals, challenges, and motivations.