SHERYL ORLOVE
Chicago, IL ***** 773-***-**** ************@*****.*** linkedin.com/in/sheryl-orlove PROFESSIONAL SUMMARY
Detail-oriented and highly collaborative project and operations leader with over 15 years of experience in managing complex initiatives across arts, insurance, and nonprofit sectors. Proven success in supporting multi-phase projects, vendor coordination, procurement oversight, and strategic communication. Known for exceptional organizational skills, stakeholder engagement, and dedication to crafting creative solutions in fast-paced environments. Passionate about supporting arts and design through effective project execution and team collaboration.
CORE COMPETENCIES
• Project Coordination & Workflow Optimization
• Procurement Support & Vendor Management
• Cross-Functional Team Collaboration
• Client & Internal Stakeholder Communication
• Microsoft Office Suite Smartsheet Adobe
• Documentation, Compliance & Recordkeeping
• Scenic/Creative Production Understanding
• Meeting Planning & Note-Taking
• CRM & Project Tracking Systems
RELEVANT EXPERIENCE
VP of Agency Operations and Compliance
Your Way Insurance LLC Chicago, IL Jul 2022 – Nov 2024
• Oversaw day-to-day project operations and compliance for over 8,000 licenses and 45,000+ carrier appointments.
• Led cross-departmental coordination ensuring project deliverables were met on time and aligned with strategic goals.
• Managed documentation workflows, ensuring clarity and timeliness across all compliance and reporting needs.
Project Manager, Lead Management & Carrier Relations Advise Insurance Chicago, IL Apr 2021 – Jul 2022
• Created project tracking and reporting strategies that improved transparency with stakeholders and external partners.
• Handled materials coordination and contributed to efficient project rollouts within business development teams.
Director of Carrier Operations and Agent Services
GoHealth LLC Chicago, IL Aug 2013 – Nov 2019
• Led project operations involving regulatory compliance and agent onboarding for over 3,000 agents.
• Partnered with vendors and internal teams to streamline project documentation and maintain up-to-date records.
• Provided leadership on process improvement initiatives that supported long-term organizational growth.
Development Research Department Head
The Art Institute of Chicago Chicago, IL Sep 2004 – Jun 2012
• Played a key role in multi-year capital projects, including the $400M Modern Wing campaign.
• Coordinated internal departments, vendors, and donors to ensure alignment of high-level fundraising deliverables.
• Maintained meticulous records and facilitated detailed briefings for meetings and events. EDUCATION
M.L.I.S., Archives & Special Collections Dominican University B.F.A., Art Education & General Studio Art Southern Illinois University AFFILIATIONS
• Co-Chair, Benefits and Fundraising – Artists Book House Board, Chicago
• Former Board Secretary – IL Chapter, APRA
• National Committee Member – Securities & Insurance Licensing Association TECHNICAL TOOLS
• Microsoft 365 Smartsheet Salesforce Adobe Raiser’s Edge
• CRM & Compliance Systems: RegEd, Sircon, AgentSync, Little Green Light
• Research Databases: DonorSearch, Lexis-Nexis