Experienced Professionals

InSightful Solutions

Darryl Siry
Chief Digital Officer

Darryl’s unique background and smarts combined make him the best Chief Digital Officer in insurance land, which is why he’s at ProSight Specialty Insurance! We lead with the best, and Darryl is a prime example. His technology leadership spans our IT efforts, our Digital Products and our Customer Service. Darryl is a dynamic leader whose legacy includes successful deployment of innovative and effective digital strategies in a diverse set of industries. Prior to joining ProSight, he was founder and CEO of NewsBasis, a software service for media relations. Previous to that, Darryl led Sales and Marketing at Tesla Motors and was SVP and Chief Marketing Officer for Fireman’s Fund Insurance Company. Darryl earned a BA in Economics from Brown University and an Executive Certificate in Technology and Operations from MIT Sloan School of Business. When he is not directing our technology activities, he’s cycling the beautiful hills of central New Jersey, as he is an avid cyclist.

Meet the Leadership Team

Joe BeneducciChairman, President and CEO


Larry HannonChief Operating Officer

MEET Larry

Bob BaileyChief Underwriting Officer


Joe FinneganCustomer Group President


Paul KushChief Claims Officer


Darryl SiryChief Digital Officer

MEET Darryl

Frank BosseChief Human Resources Officer

MEET Frank

Michael FurguesonManaging Director

MEET Michael

Lee KraemerChief Actuary Officer


Anthony PiszelChief Financial Officer

MEET Anthony

Frank PapaliaChief Legal Officer

MEET Frank

Kevin KennyStrategic Initiatives Executive

MEET Kevin

The ProSight Difference

We create unrivaled value for our customers by exceeding expectations in everything we do. We accomplish this based on our unique performance culture and a desire to succeed at uncommon challenges.

Partnering Only with Exclusive Agents

We partner exclusively with a select number of agents who share our vision of delivering value to customers through superior expertise.

Excellent Financial Strength

The underwriting members of the ProSight Specialty Insurance (ProSight) group of companies including Syndicate 1110 at Lloyd’s of London, are rated “A” (Excellent) by A.M. Best.


Get in touch

Contact Options



(973) 532-1900

Mailing address
ProSight Specialty Insurance
412 Mount Kemble Ave.
Suite 300C
Morristown, NJ 07960

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