Proven Success in Government Licensing, Fundraising, Workforce Training, and Building and Leading High-Performance Teams
Dan Weiss, CEO, Highwater Bound
•With 25+ years of leadership and entrepreneurship experience, he has designed, launched, and led organizations across financial services, fintech, and consulting, driving innovation and strategic growth.
•An expert in licensing, funding, and certifications, he has a proven track record of successfully navigating complex applications and securing approvals at state, federal, and international levels.
•As Founding CEO & Owner of Chartwell Compliance, he built and led this licensing and compliance firm for 12+ years, serving 700+ fintech and financial services clients, including Microsoft, Coinbase, Ant Financial, and Square. Organically scaling the company to middle-market size, he achieved a successful exit through acquisition by NASDAQ-listed MVB Bank, gaining unique insight into operating within a fintech bank, followed by a second exit to Ankura. A forward-thinking leader, he designed and led experiential, skills-based employee training in Gettysburg, Normandy, and Japan, while maintaining zero employee turnover for the final three years.
•As Chief Strategy and Compliance Officer and the first employee at Microfinance International Corporation, a global payments and lending fintech, he played a pivotal role in its growth over 7+ years. He secured $9 million in equity, debt, and grants from the U.S. and Dutch governments, achieved a flawless compliance record, and obtained state licenses across five financial services areas. Additionally, he established and led a profitable compliance consultancy, further expanding the company's impact.
•As an Economic Development Advisor, he helped major corporations, including PepsiAmericas and JetBlue Airways, secure large-dollar state training grants. While at a boutique tax incentives firm, he established and led this practice area, driving significant funding opportunities for corporate workforce development.
What Government Leaders Say About Dan Weiss
The former Acting Secretary, Acting Under Secretary, and Senior Assistant Secretary of the U.S. Air Force, the Honorable Tidal McCoy, shares his perspective on Dan Weiss’s leadership, strategic mindset, and ability to drive success
“I have had the privilege of knowing and observing many exceptional leaders throughout my career, and few stand out as distinctly as Dan. He possesses the boldness and courage necessary to take well-considered risks, consistently stepping outside his comfort zone to seize opportunities that others might hesitate to pursue. His ability to build and lead extraordinary teams – teams that endure, adapt, and succeed over time – Is a testament to his pragmatic and empathetic leadership.
Dan has an exceptional talent for applying military history as a guiding framework for modern business leadership, ensuring that strategy, discipline, and adaptability remain at the forefront of his decision-making.
Whether fundraising from the most complex institutions or spearheading high-stakes compliance initiatives, his results speak for themselves. He is, without question, one of the more successful and dynamic business executives I have encountered, bringing the kind of vision, resilience, and execution that drive organizations to remarkable success.
As a former All-American athlete, I recognize in Dan the same qualities that define elite competitors – unwavering focus, relentless drive, and the ability to perform under pressure. His representation of Team USA is not just a testament to his physical endurance, but also to his mental toughness and strategic discipline, traits that clearly translate into his business leadership and success.”
Dennis Lormel, the legendary former Chief of the FBI's Financial Crimes Section and the architect and Chief of its Terrorist Financing Operations Section after 9/11, highlights Dan Weiss’s leadership, expertise, and commitment to client success:
“Daniel is a straightforward and detail-oriented executive. He has assembled an extraordinarily talented cadre of subject matter experts to work with him on a variety of compliance projects. Daniel is well organized and adept at project development and execution. Daniel is cognizant of the needs of his clients and ensures their requirements are met.”
Terri Iverson, former Office of the Comptroller of the Currency National Examiner, praises Dan Weiss’s energy, integrity, and client-focused approach:
“Dan brings high and addicting energy and focus. His integrity and service standards are some of the best in the financial institution industry. He cares about his clients and has their best intentions when tailoring consulting services to the client's needs.”