Jonathan Calpas

Background

About Jonathan Calpas

I am an experienced General Counsel who oversees all legal, regulatory and compliance matters for 3 tax-exempt insurance risk pools and a services company subsidiary. These insurance enterprises provide health, workers’ compensation and property and liability coverage to ~200 unique public entity members generating ~$250M in combined annual revenue with ~$300M in assets under management. I serve as a trusted business partner to the leadership team. I negotiate, draft, review and manage contracts across all business lines/departments and counsel our member entities on contractual indemnification and insurance provisions to lessen the trust’s covered contract risk. I am comfortable with a wide variety of agreement types including insurance, reinsurance, service provider, SaaS, software development, information technology, confidentiality, financial services, investment management, brokerage, PBM, TPA, business associate, training and facilities. I manage an internal team and external vendors to ensure health plan compliance for covered lives across ~165 member entities. I collaborate closely with a respected outside lobbying firm and direct efforts to influence legislative activity at the state level. I provide insurance coverage opinions, manage our outside counsel defense rosters and advise our internal claims team on high stakes General Liability, Employment Practices Liability, Civil Rights, Public Officials, Workers Compensation and Property claims. I partner with our risk control team on targeted policy creation to reduce claim frequency and severity. I leverage legal technology and data automation to modernize processes and workflows and improve recordkeeping. I formerly worked as a business and finance associate for an AmLaw 100 law firm specializing in employee benefits and executive compensation. On a daily basis, I advised lawyers, senior management and finance/HR personnel on a wide variety of laws including ERISA, HIPAA, COBRA, ADA, ACA and the Internal Revenue Code and their implementing regulations. I frequently reviewed, designed and drafted retirement, health and welfare, and executive compensation plans along with related disclosures, employee communication materials and board-level documentation. I participated in mid-market M&A deals and co-authored 5 editions of Employer’s Guide to Health Care Reform (Aspen Publishers: 2010-2015). Prior to becoming a lawyer, I worked in corporate accounting for a Fortune 50 company for 5 years and became licensed as a CPA (currently in inactive status) while attending law school.