Rob Shapiro
Greenwich,CT
Summary
Application specialist and essay coach focused on mentoring and writing instruction. Developed proprietary worksheets and structured frameworks to improve essay clarity and quality. Authored 600+ essays and delivered admissions-focused writing support.
Overview
16
16
years of professional experience
Work History
Retirement & Benefits Specialist
New York Medical College
Valhalla, NY
09.2024 - Current
- Administered comprehensive retirement and employee benefit programs, providing essential support to faculty, staff, and administration.
- Guided employees through complex policy structures and plan options, ensuring clear communication and personalized support.
- Ensured regulatory compliance and streamlined processes by facilitating effective cross-departmental coordination within a higher education medical institution.
Life Insurance & Employee Benefits Broker
Rob Shapiro Insurance Solutions (RSIS) / Clarity Insurance Group
Greenwich, CT
01.2018 - Current
- Advised personal and corporate clients on life, health, group benefits, Long-Term Care insurance coverage, enhancing clients' understanding of options.
- Developed customized buy/sell life insurance and risk mitigation strategies for high-net-worth clients and hedge funds, addressing complex financial needs.
College Essay Writer & Application Specialist
Always A Writer
Greenwich, CT
02.2016 - Current
- Coached high school seniors through each stage of college application essay development, helping shape authentic personal narratives.
- Supported high school students with essay writing and college admissions guidance as a volunteer for Luca, building application readiness and confidence.
- Created student worksheets and writing frameworks that helped applicants identify meaningful personal experiences while keeping individual voice intact.
- Wrote 600+ essays for LinkedIn blog #StayTuned and published an ebook #StayTuned: Essential Essays, adding to online conversations on college admissions and essay strategy.
Chief Risk Officer
Bloomberg Tradebook
New York, NY
08.2010 - 03.2017
- Supported the development of Bloomberg's initial enterprise risk management (ERM) framework using the COSO framework to improve risk identification and response.
- Monitored operational risk across global business units and implemented key risk metrics and governance controls to strengthen risk management practices.
- Directed risk governance for Bloomberg Tradebook electronic trading and agency brokerage operations.
- Reviewed market, credit, and operational risk across trade capture and order routing.
- Built controls for best execution trading surveillance and exception escalation.
Education
Bachelor of Business Administration (BBA) - Finance
University of Michigan – Ross School of Business
Ann Arbor, MISkills
- Content editing
- Essay coaching
- Storytelling and close reading
- Student mentorship
- Higher education management
- Employee benefits administration
- Benefits design
- Regulatory compliance
- Risk management
- Client relations and collaboration
- Process optimization
VOLUNTEER WORK
LUCA (Latino U College Access), White Plains, NY, 2021, 2024, Provided college essay tutoring/mentoring assistance to Latino high school students who would be the first in their family to attend college.
Timeline
Retirement & Benefits Specialist
New York Medical College
09.2024 - Current
Life Insurance & Employee Benefits Broker
Rob Shapiro Insurance Solutions (RSIS) / Clarity Insurance Group
01.2018 - Current
College Essay Writer & Application Specialist
Always A Writer
02.2016 - Current
Chief Risk Officer
Bloomberg Tradebook
08.2010 - 03.2017
Bachelor of Business Administration (BBA) - Finance
University of Michigan – Ross School of Business