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Sim Shain began their career in 1996 as a Paramedic at Hatzolah EMS. In 2007, they joined MONOC EMS in the same role. In 2009, Sim became the Director of Strategic Partnerships at Banquest Payment Systems. In 2010, they were appointed Chief Executive Officer of ParaFlight Aviation- Inc. 5000 Company. In 2020, Sim took on the role of Chief Executive Officer at OrganFlights.com, as well as a Paramedic at RWJBarnabas Health.

Sim Shain obtained a Bachelor's degree in Talmudic Studies from Talmudical Academy-New Jersey between 1987 and 1991. In 2007, they obtained a National Registered Paramedic (NRP) certification from the National Registry of Emergency Medical Technicians and a Paramedic certification from the NJ Department of Health. In 2014, they obtained a Flight Paramedic certification from ParaFlight EMS and Aviation. In 2017, they obtained a NBAA Certificate of Membership from the National Business Aviation Association and a Commercial Medical Escort certification from the Medical Escort Association. In 2019, they obtained a Paramedic certification from United Hatzalah of Israel. In 2020, they obtained an Open Water Diver certification from PADI. In 2021, they obtained a Certified Chaplain certification from the United States Chaplain Corps (USCC). Sim also holds an Extrication Technician certification from the Bergen County EMS Training Center.