Dillard Trapp
Founder & CEO | Simply Trapp Solutions
Co-Founder | Just Ice Served
Co-Founder | Seaside Supreme Solutions
Pensacola, Florida | Gulf Coast
Industry: Technology
Sector: Cybersecurity & Risk Management Consulting
Specialties: Cybersecurity Strategy | Governance, Risk & Compliance (GRC) | FedRAMP & Federal Cloud Compliance | Cloud Security | AI Security | Enterprise Risk Management
🌐 Website
Leadership Focus
Digital Resilience | Entrepreneurial Leadership | Innovation | Mentorship | Community Building
CityBox Executive Essence™
Dillard Trapp is a cybersecurity leader, entrepreneur, and U.S. Marine Corps veteran whose work brings together technology, risk management, business creation, mentorship, and community leadership.
As Founder & CEO of Simply Trapp Solutions, Trapp helps organizations navigate increasingly complex cybersecurity, governance, compliance, cloud-security, and enterprise-risk environments. His entrepreneurial leadership extends beyond technology through his roles as Co-Founder of Just Ice Served and Co-Founder of Seaside Supreme Solutions.
Executive Overview
Dillard Trapp leads Simply Trapp Solutions, a Pensacola-based cybersecurity and risk-management consulting firm serving organizations navigating cybersecurity strategy, governance, cloud compliance, technology risk, and organizational resilience.
A Certified Information Systems Security Professional (CISSP) and Project Management Professional (PMP), Trapp brings more than a decade of information-security experience spanning government and private-sector environments. His work includes federal cloud compliance, FedRAMP, Department of Defense requirements, security frameworks, and cloud-security environments.
His leadership, however, extends beyond cybersecurity.
Through Just Ice Served and Seaside Supreme Solutions, Trapp has expanded into additional entrepreneurial ventures, demonstrating an ability to apply business-building, relationship development, and strategic thinking across industries. Just Ice Served, which he co-founded, operates within Pensacola's food-and-beverage and hospitality ecosystem through premium specialty ice products.
This combination of technical expertise and cross-sector entrepreneurship gives Trapp a leadership profile that bridges cybersecurity, innovation, business development, mentorship, and community engagement.ilosophy centered on service, entrepreneurship, innovation, and creating long-term value across multiple sectors.
Why This Leader Matters
Technology risk has become business risk.
Artificial intelligence, cloud computing, regulatory requirements, cybersecurity threats, and digital transformation increasingly affect organizations at the executive level. Leaders must understand not only how technology works, but how security decisions influence operations, compliance, reputation, growth, and long-term resilience.
Trapp operates within that intersection.
His work helps translate highly technical security and compliance environments into strategic considerations organizations can understand and act upon. At the same time, his entrepreneurial ventures demonstrate that his leadership perspective is not confined to technology consulting.
He is also building businesses, mentoring emerging professionals, participating in regional technology conversations, and contributing to initiatives designed to strengthen Pensacola's entrepreneurial and leadership community.
His leadership illustrates the increasing value of executives who can move across disciplines while maintaining a clear foundation of expertise.
CityBox Leadership Signals™
Strategic Orientation
Integrating cybersecurity, risk management, regulatory readiness, emerging technology, entrepreneurship, and long-term organizational resilience.
Decision Style
Analytical, mission-driven, structured, and future-oriented, combining established security frameworks with entrepreneurial thinking and practical business considerations.
Primary Influence
Cybersecurity strategy, federal cloud compliance, governance and risk, artificial intelligence security, entrepreneurship, executive advisory, mentorship, and regional innovation.
Leadership Strength
Translating complex technology and security challenges into practical business decisions while applying entrepreneurial thinking across multiple ventures and industries.
Executive Signature
Building resilience. Creating opportunity. Leading across boundaries.
Leadership Environment
Cybersecurity, federal and commercial technology environments, cloud compliance, entrepreneurship, emerging technology, hospitality ventures, mentorship, and Gulf Coast business and civic communities.
Selected Leadership Milestones
Dillard Trapp’s leadership record reflects cybersecurity expertise, military service, multi-venture entrepreneurship, emerging-technology thought leadership, mentorship, and community engagement.
Cybersecurity & Federal Cloud Leadership
Trapp has built more than a decade of experience across information security, risk management, compliance, and cybersecurity leadership.
In addition to founding Simply Trapp Solutions, he serves professionally in federal cloud compliance and assessments, supporting federal and commercial organizations navigating FedRAMP, Department of Defense, cloud-security, and regulatory environments.
Multi-Venture Entrepreneurship
Beyond Simply Trapp Solutions, Trapp is Co-Founder of Just Ice Served and Seaside Supreme Solutions, extending his entrepreneurial portfolio beyond cybersecurity.
Just Ice Served has established a presence within Pensacola's food-and-beverage community with premium sculpted specialty ice designed for elevated beverage experiences.
His involvement across multiple ventures reflects an entrepreneurial approach built around recognizing opportunities, developing relationships, and creating businesses across different market environments.
AI & Cybersecurity Thought Leadership
Trapp contributes to conversations surrounding the evolving relationship between artificial intelligence and cybersecurity.
At Hack the Coast 2026 in Pensacola, he spoke on security architecture for autonomous AI agents, addressing the need for security guardrails as artificial-intelligence systems become increasingly autonomous.
Mentorship & Community Leadership
Trapp's leadership includes mentorship and initiatives intended to strengthen the next generation of professionals and community leaders.
His broader work has included involvement with Pillars of Promise, youth mentorship, technology-community engagement, and TEDxPensacola, extending his impact beyond his businesses into leadership development and community-building.
CityBox Magazine Cover Star
Dillard Trapp is a CityBox Magazine Cover Star, with an extensive editorial experience documenting his journey as an entrepreneur, cybersecurity strategist, mentor, and community leader.
His CityBox editorial record also includes his work with Simply Trapp Solutions and his entrepreneurial involvement with Just Ice Served, connecting his technology leadership with the broader business and cultural ecosystem of Pensacola.
CityBox Connections
CityBox identifies leaders whose experience and areas of focus may create meaningful opportunities for collaboration.
Todd Thomson
Technology, artificial intelligence, and cybersecurity are becoming increasingly important to economic development, workforce readiness, and the long-term competitiveness of regional businesses.
Troy Rafferty
As organizations adopt emerging technologies, legal strategy, cybersecurity, privacy, governance, and risk management continue to become more closely connected.
Kelvin Singleton
Cybersecurity strategy and enterprise security leadership naturally complement artificial intelligence adoption, helping organizations innovate while protecting critical systems, data, and business operations.
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