who we are

About us

At O’ShaughnaHill Surety & Insurance, Inc. (OSI) we specialize in providing direct bail bonds insurance services. Whether you’re a novice or a veteran in the industry we’ll help guide every agent to maximize efficiency and fuel growth. In addition to our premium service, marketing expertise, and advanced bail bonds technology, we also provide our agents the most competitive rate in the state.

Apply today
work with the experts

Made by Bail Agents for Bail Agents

Founded, owned, and operated by licensed Florida bail agents. At OSI we are committed to strengthening the foundation of our agents for the future of our industry. Our team has the knowledge and experience for a true understanding of procedures on how retail bail operates. Thats why we are available 24/7 to assist, advise, and resolve any issues that may arise for every OSI agent.

We believe in educating our agents

advancing the industry

OSI works in tandem with our bail agents to inform, educate and proactively address any reforms or updates to our industry. When you join the OSI team every facet of your bail bond needs are backed by our qualified experts. So, no matter the challenge you may face, we have you covered!

we’re here to help

Available for you 24/7

Our services are offered around the clock, seven days a week, and include: bond transfers, large bond approval, and surety bail inquires. We provide the tools, advice, support, and service for unparalleled success. At O’ShaughnaHill Surety & Insurance, Inc. WE EMPOWER OUR AGENTS!

Peter Hill

// Co-founder and CEO

Peter Hill serves as Chief Executive Officer (CEO), and is one of the co-founders, of O’ShaughnaHill Surety & Insurance, Inc (OSI). He holds an active Florida bail bond license, has over a decade of retail bail experience, and over 15 years experience in premier customer service. Upon founding OSI Peter shifted his expertise to focus on bringing to fruition his vision of a surety provider that not only provides financial backing, but also the tools required to achieve optimal results in the Florida bail bond industry.

He maintains his relationships in state and local politics to ensure accountability and the right to bail in our criminal justice system. He is an active member of the Florida Bail Agents Association, Professional Bail Agents of the United States, and American Bail Coalition. His devotion to the industry is unmatched in enthusiasm and determination. He is committed to the highest ethical and professional standards within his company. He empathizes with agents on the struggles of retail bail making himself readily available to assist in promoting reliable growth and continued development of each OSI agent. He imbues his fleet of agents with a sense of empowerment that can come only from being backed by a leader. Peter Hill is a true maverick in his enterprise and looks forward to sculpting future entrepreneurs to empower themselves into true success.

kevin o’shaughnessy

// Co-founder and president

Kevin O’Shaughnessy is one of the co-founders and president of O’ShaughnaHill Surety & Insurance, Inc (OSI). After serving our great country in the United States Armed Forces, he worked as a corrections officer acquiring invaluable insight into our criminal corrections system. He went on to begin development of his entrepreneurial and management skills by working in a variety of successful businesses. Shortly thereafter, friend and mentor, Mel Barth, inspired Kevin to enter the profession of bail bonds where he developed a specialization in fugitive recovery. Kevin O’Shaughnessy’s knowledge, expertise, and passion for the bail industry, coupled with a wealth of experience in entrepreneurship, allow him to offer guidance, mentorship, and superior service to all agents of OSI.

Sam Jochananov

// Chief Operations Officer (COO)

Sam Jochananov serves as Chief Operations Officer (COO) of O’ShaughnaHill Surety & Insurance, Inc. He has earned over 25 years of experience in the bail industry. Sam dove into the world of bail bonds as an entry level agent specializing in fugitive recovery. He raced up the ranks, achieving the position of Managing General Agent (MGA).

In 2018, Sam joined the administrative staff at Financial Casualty & Surety, Inc. It was from there that he pursued, and was appointed, a senior level position at OSI. Sam’s executive position affords him the opportunity to assist in the rise of a company that offers hands on mentorship to their agents, and grants him the freedom to administer the highest quality services for OSI Agents. At OSI he has been able to grow, not only his own wealth of knowledge and expertise, but a company that empowers its bail agents with the skills they need to reach their own maximum potential.

In addition to his bail bonds experience, Sam boasts an accomplished musical career, and a background in audio engineering. He brings with him this rounded background to ensure that his vision for OSI is achieved. His daily goal for OSI operations is that agent provisions always be tailored to the unique need of each individual, so that OSI agents are always empowered to achieve ultimate success.

Ronald Weinbaum

// Chief financial officer (CFO)

Ronald Weinbaum, CPA is the Chief Financial Officer (CFO) for O’Shaughnahill Surety & Insurance, Inc.  He oversees the financial operations of the company and ensures OSI remains in statutory financial compliance with the insurance department.  Ronald graduated from the University of Massachusetts with a BBA in Accounting and earned his Master of Science in Taxation from Florida Atlantic University.    Ronald has been in the property and casualty financial area for the past 20 years providing services such as auditing, forensic accounting, CFO, consulting, and regulatory compliance services.  Ronald has also testified as an expert witness on several cases for the State of Florida involving statutory accounting issues.  Ronald is tasked with monitoring OSI’s financial landscape as the company continues to grow and add additional bail bond agents.