Robert Schapp: From IT to Servant Leadership

With a remarkable career spanning diverse industries, Robert Schapp is a prominent figure in the insurance and protective services sector. As the Chief Administrative Officer at Travelers Protective Association (TPA), Robert has harnessed his years of expertise and industry knowledge to nurture a culture of community, connection, and service. His commitment to high-touch leadership and human connection has earned him recognition as a leader, making a significant impact on the lives of TPA members and the broader community.

Robert’s Remarkable Journey to TPA

The present role represents the pinnacle of Robert’s career, where his diverse experiences in finance, technology, nonprofit work, and charitable and fraternal organizations are in one place. With a background that spans roles in the Shriners, financial services, IT, analysis, and nonprofit board chairmanship, Robert holds a unique blend of different skills and perspectives. Now, as the Chief Administrative Officer of TPA, he has found a platform where his expertise comes together in a way that feels both natural and fulfilling. Notably, the opportunity to lead TPA was compelling enough to bring Robert out of retirement, underscoring the alignment of this role with his passions and strengths.

“Servant Leadership” in Action

As a leader, Robert embodies the philosophy of servant leadership, where he mainly focuses on helping everyone and empowering them to be successful. By positioning individuals for success, offering necessary resources, and nurturing an open community, Robert strives to create an environment where everyone can thrive. He believes that most failures stem from breakdowns in communication, not technical issues, and thus actively works to eliminate silos and promote collaboration. Leading with integrity and a commitment to follow-through, Robert builds trust and influences outcomes through a selfless approach. Robert has always believed in the wisdom of the Harry Truman quote: “It is amazing what you can accomplish if you do not care who gets the credit.” That mindset shapes how he builds trust, influences outcomes, and creates an environment where everyone can thrive.

A Distinctive Approach to Cross-Functional Communication

According to Robert, clear and inclusive communication is the foundation of successful cross-functional teams. To accomplish this, he prioritizes eliminating silos and fostering open dialogue among team members and external partners. By connecting people and encouraging collaboration, Robert promotes a deeper understanding of each other’s roles through cross-training and job shadowing. The bigger picture leads to a stronger relationship, more effective collaboration, and better outcomes.

Empowering Communities through Connection and Service 

TPA stands out due to its commitment to providing a safety net and fostering genuine personal connections in an increasingly impersonal world. By promoting mental health through meaningful social opportunities and partnering with organizations to address the community’s needs, TPA is evolving to remain relevant in the current growing era. The organization’s mission is multifaceted, focused on championing hearing inclusion, advocating for better and safer communities, providing supplemental accident insurance, and offering social and service opportunities for its members. TPA strives to extend its impact and create a thriving world where everyone can thrive through its local posts and charitable arm.

Analytical Decision-Making with Emotional Intelligence

Robert’s decision-making process is guided by a simple question: What’s the right thing to do? The answer often comes from a balance of both analytics and empathy, grounding decisions in data but also weighing what he sees with his eyes, hears with his ears, and feels in his heart. This approach enables him to navigate complex situations with empathy and integrity, prioritizing what’s right, not just what’s easy or expedient.

Impact Beyond Core Services

TPA supports communities through various initiatives, including the TPA Hearing Trust, which provides vital assistance to individuals with deafness or hearing loss, helping thousands access hearing devices, specialized treatments, speech classes, interpreters, note-takers, and more.

The organization also maintains the Homer T. Wilson Humanitarian Fund, which has been providing emergency f inancial aid to members for over a century. One of TPA’s greatest strengths is the way its members step up for their communities.

Child safety and welfare remain a priority for them. Many posts still distribute “Watch That Child” bumper stickers for school buses and CHAD identification stickers, an initiative taken over from the Illinois Department of Transportation some years ago to help protect children in emergencies. Through these programs and countless volunteer-driven projects, TPA members make a tangible difference well beyond the core mission.

Adapting to Industry Shifts

In the past decade, the insurance and protective services industry has grown increasingly competitive and specialized. On the insurance side, TPA has leveraged its unique identity as a membership-based, fraternal community service organization. By focusing on its core values and designing benefits as member perks instead of products to sell, TPA has carved out a distinct niche. This approach allows the organization to provide meaningful coverage while also fostering a sense of belonging and service among its members.

Promise and Risk Amid Emerging Technologies 

Emerging technologies like AI, data analytics, and digital engagement offer tremendous opportunities for TPA to expand its reach and connect with others more effectively. But TPA recognizes the risk of losing sight of what makes it unique: personal connections, interpersonal growth, and a sense of belonging that come from being part of something bigger. The challenge lies in harnessing technology to enhance human relationships, instead of replacing them, and ensuring digital tools serve the organization’s mission without compromising its core values.

Remarkable Achievements Along the Way

As an IT Project Leader for a Fortune 50 company, Robert led a project that automated financial and management reporting for 50 semi-autonomous divisions nationwide. This complex project required collaboration with multiple stakeholders, including IT teams, vendors, and software developers. Robert secured their buy-in and ensured a smooth implementation by including divisions in the design and testing processes. The success of the project highlighted his ability to break down silos and drive communication and collaboration.

Words of Wisdom 

Robert advises aspiring leaders to build a strong network across multiple fields. By building relationships and seeking out mentors who support their long-term goals, individuals can gain valuable connections, perspectives, and opportunities. This strategic approach can ultimately prepare them to lead across disciplines.

Robert’s Take on High-touch Leadership

For him, “high-touch leadership” is about genuine human connection. In an increasingly digital and remote-first world, leaders who prioritize person-to-person interaction and authentic engagement will be harder to find, yet their impact will be great. High-touch leaders build trust, prevent silos, and reinforce the value of each person within the organization by connecting with people as individuals and building a foundation that technology alone cannot replicate.

TPA’s Future Outlook 

Robert envisions the TPA evolving over the next few years by leveraging technology and social media to expand its reach and impact. The TPA Hearing Trust will be a key part of the organization’s brand and new membership models and partnerships will be explored. TPA will preserve its fraternal and social benefits while delivering supplemental accident protection, community service, and personal connection to more people in more places. “In short, we’ll build on our heritage not as a hitching post that holds us back, but as a stepping stone toward an innovative, inclusive, and future-focused TPA,” asserts Robert.