We sat down with Digitalized Software’s Vice President of Sales Jason Donnay to explore his journey, leadership philosophy, and the unique perspective he brings to our team. Jason joined Digitalized Software in its early days, bringing nearly a decade of experience in the software industry and a deep passion for customer success. Beyond his professional achievements, Jason serves his community as a volunteer firefighter, embodying the same commitment to service that drives his approach to business.
Below is our conversation with Jason about his role, his approach to customer relationships, and how his values shape both his professional and personal life.
Joining Digitalized Software
Q: What drew you to Digitalized Software, and how has your role evolved since joining the team?
A: “I was immediately drawn to Digitalized Software’s mission of freeing people from mundane, manual tasks so they can focus on higher-value work. Having spent years in the software industry, I’ve seen how the right technology can truly transform operations, and Received Digital represents exactly that kind of transformational solution.
When I joined as VP of Sales, I was excited to lead not just a sales team, but a customer success organization. My role has evolved from simply driving revenue to building a comprehensive approach that ensures our clients achieve maximum value from our platform. We’ve built a team that doesn’t just sell software—we partner with organizations to solve real business problems and create lasting impact.”
Leadership philosophy and intention
Q: You’re known for your customer success philosophy of “seek to understand, not be understood.” How does this approach influence your team’s interactions with clients?
A: “This principle is fundamental to everything we do. Too often in sales, there’s a rush to present solutions before truly understanding the problem. I’ve trained my team to lead with curiosity and genuine interest in our clients’ unique challenges.
When we engage with a mail center operator at a university or a facilities manager at a Fortune 500 company, our first goal is to deeply understand their current processes, pain points, and what success looks like for them. Only then can we demonstrate how Received Digital can deliver specific value. This approach has resulted in stronger relationships, better implementations, and clients who become true advocates for our platform.”
Q: Can you explain the “1% rule” and how it applies to both personal and professional development?”
A: “The 1% rule is about incremental improvement each day. It’s about the compound effect of small, consistent gains. In our fast-paced industry, it’s easy to look for dramatic breakthroughs, but real transformation happens through daily commitment to getting slightly better.
For my team, this might mean improving our discovery process, refining our demo presentations, or enhancing our follow-up strategies. Personally, it applies to staying current with industry trends, developing new skills, or simply being more present in my interactions. When you improve by just 1% each day, you’re 37 times better by the end of the year. That’s the power of consistent, focused effort.”
Personal values and their professional impact
Q: You live by the concept of the ‘5 Star Day’—Family, Health, People, Work, Focus. How do you balance these priorities?
“The 5 Star Day framework keeps me grounded and ensures I’m investing energy in what truly matters. Each element is interconnected and reinforces the others.
Family comes first—they’re my why and my motivation. Health gives me the energy to show up fully for my family, my team, and our clients. People include the relationships I build with colleagues, customers, and my community. Work is about making a meaningful contribution through Digitalized Software. And focus ties it all together—being intentional about where I direct my attention.
Some days I might excel in all five areas, other days I might focus more heavily on one or two. The key is being conscious about these priorities and making decisions that honor what’s most important.”
Q: Beyond your role at Digitalized Software, you serve as a volunteer firefighter. How does this experience influence your approach to business?
A: “Being a volunteer firefighter has profoundly shaped how I approach business and life. In emergency response, you learn to stay calm under pressure, make quick decisions with incomplete information, and work seamlessly as part of a team where everyone’s safety depends on each other.
These skills directly translate to my role at Digitalized Software. When a client faces an urgent challenge with their mail processing, I approach it with the same urgency and systematic problem-solving I use in emergency situations. Both roles are fundamentally about service and helping people when they need it most.
The firefighting experience also reinforces the importance of preparation and continuous training. Just as we drill regularly to be ready for emergencies, I ensure my team is continuously developing skills and knowledge to serve our clients better.”
Growth strategies in a competitive market
Q: What strategies does your team employ to ensure Digitalized Software’s continued growth in the competitive SaaS market?
A: “Our strategy centers on three pillars: deep customer understanding, value based selling, and long-term relationship building.
First, we invest heavily in understanding our target markets—higher education, corporate facilities, government agencies. We attend industry conferences like NACUMS and NPF, engage with mail center management professionals, and stay connected to the evolving challenges in mail and package management.
Second, we practice value based selling rather than transactional sales. We don’t just demonstrate features; we show specific business outcomes and ROI.
Finally, we focus on customer lifetime value rather than just initial deals. Our success is measured not just by new client acquisition but by client retention, expansion, and advocacy. When clients see genuine value and feel supported, they become our best sales partners.”
Envisioning the future of mail centers
Q: How do you see the future of mail center operations, and how do you think Digitalized Software is positioned for that future?
A: “The future of mail center operations is undoubtedly digital, but it’s not just about technology—it’s about reimagining the entire process around efficiency, transparency, and recipient experience.
We’re seeing organizations recognize that mail and package management isn’t just a back-office function; it directly impacts employee satisfaction, operational efficiency, and even organizational reputation. Received Digital positions our clients ahead of this curve by providing real-time visibility, automated workflows, and data insights that transform how they think about inbound processing.
With our 20+ years of postal industry expertise combined with modern software development capabilities, we’re uniquely positioned to help organizations navigate this transformation. We’re not just digitizing existing processes—we’re helping them reimagine what’s possible.”
Final thoughts
Jason’s approach to sales leadership, grounded in service, continuous improvement, and genuine care for both clients and team members, reflects the core values that drive Digitalized Software’s success. His commitment to understanding before being understood, combined with his real-world experience in emergency response, brings a unique perspective to our organization.
As Jason continues to lead our sales and customer success efforts, his focus remains clear: helping organizations transform their operations while ensuring every team member and client feels valued and supported. Whether responding to an emergency call as a volunteer firefighter or helping a client optimize their mailroom operations, Jason’s dedication to service and positive impact shines in everything he does.
