Charles Sybert in

Charles Sybert

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VP, Strategic Program Executive at Insurity
📍 Cook County, Illinois, United States

Charles Sybert is a VP, Strategic Program Executive at Insurity with over 24 years of experience in insurance technology. He specializes in large-scale, technology-driven business solutions, process innovation, and executive leadership, holding a B.S. from DePaul University. Colleagues describe him as well-organized, thorough, reliable, and detail-oriented.

Outside of his professional life, Charles is passionate about animal welfare. He actively volunteers his time with Recycled Rotts, a Rottweiler rescue organization, where he helps transport dogs to receive veterinary care and find new homes, demonstrating a strong commitment to community involvement.

He has a passion for giving dogs a second chance, personally transporting rescue animals like a Rottweiler named "Courage".

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Experience
27 Years
Current Role
VP, Strategic Program Executive
Job Level
Leadership
Location
Cook County, Illinois, United States
Personality Overview

How Charles shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Charles cares about

Insurance Innovation
His career focuses on blending deep insurance expertise with cutting-edge technology to redefine the industry, optimize operations, and enable sustainable growth for clients.
AI-Augmented Delivery
His current role involves operationalizing generative AI and agentic workflows within the insurance sector, indicating a focus on next-generation technology solutions.
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Career

Work history

7-2025
VP, Strategic Program Executive
Insurity
12-2024 - 7-2026
Principal – Strategic Growth
Wikifri
2020 - 12-2024
Vice President Insurance
RCG Global Services
2019 - 2020
Director
RCG Global Services
2016 - 2020
Managing Consultant
Majesco
In the press

Media appearances

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Education
B.S
DePaul University
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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