Drew Doleski in

Drew Doleski

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Vice President, Product Strategy at Cocoon Home Services
📍 Chicago, Illinois, United States

Drew Doleski is the VP of Product at Cocoon Home Services, an executive with deep expertise at the intersection of P&C insurance and technology. He has a background in scaling new products, focusing on IoT and AI. People who have worked with him describe him as execution-oriented and even-keeled.

Originally from the Chicago area, where he attended Loyola University, Drew now resides in Nashville. He is involved in local philanthropy, regularly supporting the Vanderbilt Comprehensive Care Clinic with his wife and friends, and enjoys attending fundraising events like the Ruby Gala.

He has built a career focused on leveraging sensitive consumer data, from telematics to smart homes, while championing transparency and customer consent.

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Experience
15 Years
Current Role
Vice President, Product Strategy
Job Level
Senior
Location
Chicago, Illinois, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Drew cares about

Proactive Home Care
His current role at Cocoon and recent posts emphasize helping homeowners invest in preventative maintenance to reduce risk, stress, and future losses.
Insurance & Technology
His entire career, from Verisk to American Family Insurance and Cocoon, has centered on integrating IoT, telematics, and AI into the insurance industry.
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Career

Work history

8-2025
Vice President, Product Strategy
Cocoon Home Services
10-2023 - 7-2025
New Products & Partnerships - Strategy & Innovation
American Family Insurance
10-2021 - 10-2023
Director, New Product Development & Strategy - Property COE
Homesite Insurance
4-2020 - 10-2021
Director, Product Management & Strategic Marketing
Verisk
11-2017 - 4-2020
Senior Product Manager
Verisk
In the press

Media appearances

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Education
2005 - 2009
B.B.A.
Loyola University Chicago
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

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