Drew Doleski

Collaborator
DISC Type : is

Vice President, Product Strategy at Cocoon Home Services

Chicago, Illinois, United States

Overview

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.

Personality Overview

Example Driven

Good Listener

Appreciative

Unlike D or C types, they are calm as well as friendly and can give the impression of being more receptive than they actually are.  They are more likely to opt for solutions that are proven in the market. Scenarios where both sides can come out as winners appeal to them greatly.

Topics They Care 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.
Data Transparency
He has publicly stated his belief that products using sensitive consumer data must lead with transparency, affirmative consent, and customer-centric protocols.

Media Appearances

Drew has no verified media appearances

Work History

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

Education

2005 - 2009
B.B.A. from Loyola University Chicago

More Information

Social Presence :

Prographics :

Exp : 15 Location : Chicago, Illinois, United States Job Level : Senior Designation : Vice President, Product Strategy at Cocoon Home Services
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Insights For Selling To Drew

During A Call Or A Meeting

DO's

  • Use phrases like ‘trust me when’, ‘your team will love’ etc.
  • When asking them questions, sound relatable and informal
  • Take time to make them feel comfortable before getting to the main pitch

DONT's

  • Don’t give the impression of being unproven or risky
  • Don’t ask too many questions that sound too dry and objective
  • Don’t get into excessive details unless prompted

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Drew is

  • Relationships can play a major role, followed by low risk and strong market validation.
  • Will you ever get a clear answer from Drew

  • They are not very direct, and unlikely to say no to your face.

Insights For Deal Planning

    How fast (or slow) will Drew move?

  • They can take their time to make decisions, even if they are constantly involved and friendly.
  • Can Drew take some risk or not?

  • It is unlikely that they will take many risks.

You And Drew

Personality Compatibility


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