Meet the Team

A proven strategist and problem solver at heart, Jarryd’s philosophy is that an insurance policy is the last step in the Risk Transfer and Risk Management process. His strategic vision and passion for problem-solving foster out-of-the-box thinking throughout the organization. His passion and creativity led to his recent departure from the conventional brokerage arena.

A University of Delaware alumnus, his collegiate athletic career closed in a leadership role as a captain of the University’s D-1 Men’s Lacrosse program. To this day, he is influenced by “instant replay”—when the tape is reviewed, there is only evidence—no excuses.

“His door is always open, and his cell phone is always on.”

Chester brings a competitive athlete’s accountability to how Boulder operates—structured process, tight execution, and ownership of outcomes. A high-level competitor across ice hockey and golf, he played at Delbarton and later competed in college golf at Villanova.

He’s also earned significant amateur golf recognition—including winning the MGA Mid-Amateur Championship (2024) and being listed by the New Jersey Golf Foundation as an MGA / NJ Golf Champion on its Advisory Council, and New Jersey Golf Association 2024 Fourball Champion.

“Teaching and serving bring him joy! He always asks how he can help.”

Tiffany is a high-impact Chief Operations Officer with more than two decades of leadership experience in the insurance industry. Since beginning her career in 2004, she has developed deep expertise across both Personal and Commercial Insurance, with a particular focus on serving high-value and VIP clientele who require sophisticated, tailored risk management solutions.

Throughout her career, Tiffany has been recognized for driving operational excellence, strengthening organizational performance, and transforming complex insurance operations into streamlined, scalable systems. She has led cross-functional teams, elevated service delivery models, and built processes that enhance underwriting precision, client experience, and long-term profitability.

Known for her strategic mindset and commitment to precision, Tiffany brings a rare combination of industry depth, operational rigor, and client-centric leadership. Today, as COO, her work is defined by a dedication to innovation, disciplined execution, and delivering risk management strategies that meet the evolving needs of both individuals and businesses.

“Excellence is built, not claimed.”

Scott is a business attorney who began his career as a litigator before moving into corporate and transactional work. His background brings litigation-trained discipline to contracts, coverage issues, and governance—so decisions and documentation withstand scrutiny. He’s also assisted several companies as General Counsel and his experience on the inside of businesses allows him to help companies make the most practical, business-oriented decisions.

Scott is extremely active in his local community, including coaching a variety of sports, serving as Vice President of Chester Basketball as well as a number of other advisory and strategic Boards.

“Meticulous problem solver that leaves no stone unturned.”