10 W. R. Berkley underwriting leaders
Michael McKinley, VP, Chief Underwriting Officer at Berkley Southeast, is one of these W. R. Berkley underwriting leaders, who lead underwriting at Berkley units such as Berkley Small Business Solutions, Key Risk and Berkley Professional Liability. A reader can learn how underwriting leaders work at W. R. Berkley from people who have held the role.
Professionals to explore
Greg Tardy, CPCU, ARM
LinkedInExperience: Vice President, Underwriting & Quality Assurance · Key Risk (a Berkley Company)
Greg Tardy has been Vice President, Underwriting & Quality Assurance at Key Risk (a Berkley Company) since January 2012, based in Greensboro, North Carolina. Greg Tardy was Underwriting Director at Summit from 2007 to 2011 and Underwriting Director at K&K Insurance Group, Inc. from 2000 to 2002.
Jason Beauchene LSSBB, CLCS, AU, AIS
LinkedInExperience: Vice President of Underwriting - Main St · Berkley Small Business Solutions (a Berkley Company)
Jason Beauchene has been Vice President of Underwriting - Main St at Berkley Small Business Solutions (a Berkley Company) since July 2025. Jason Beauchene was Manager, Commercial Lines Underwriting at Preferred Mutual Insurance Company from 2020 to 2025 and Manager, Middle Market Commercial Underwriting at Nationwide from 2017 to 2020.
Joe Rugnetta
LinkedInExperience: Vice President - Underwriting Development · Berkley Meridian (a Berkley Company)
Joe Rugnetta has been Vice President - Underwriting Development at Berkley Meridian (a Berkley Company) since September 2026. Joe Rugnetta was Senior Vice President - Underwriting at Vela Insurance Services (a Berkley Company) from 2012 to 2024 and Vice President - Specialty Casualty at Berkley Specialty Underwriting Managers LLC from 2004 to 2012.
Kathleen (Katie) Fleming, CPCU, AU
LinkedInExperience: Vice President Transportation Underwriting · Berkley Small Business Solutions (a Berkley Company)
Kathleen (Katie) Fleming has been Vice President Transportation Underwriting at Berkley Small Business Solutions (a Berkley Company) since August 2024 and Vice President Underwriting & Operations there since January 2025. Kathleen (Katie) Fleming was Assistant Vice President Underwriting at Berkley Prime Transportation (a Berkley Company) from 2021 to 2024.
Ken Traylor, CPCU
LinkedInExperience: VP-Underwriting Officer · Berkley Regional Specialty Insurance Company
Ken Traylor has been VP-Underwriting Officer at Berkley Regional Specialty Insurance Company since October 2010, based in Scottsdale, Arizona. Ken Traylor was President at Zurich E&S Brokerage from 2006 to 2010, AVP-Underwriting at Zurich Group Captives-Alternative Solutions from 2004 to 2006 and Treaty Underwriting Director at Kemper Reinsurance & GE Reinsurance from 1996 to 2000.
Michael McKinley
LinkedInExperience: VP, Chief Underwriting Officer · Berkley Southeast (a Berkley Company)
Michael McKinley has been VP, Chief Underwriting Officer at Berkley Southeast (a Berkley Company) since November 2025, and the profile says the role provides strategic leadership for the underwriting discipline. Michael McKinley was Sr. Vice President at AXA XL from 2022 to 2025 and Vice President, Controlled Insurance Programs at XL Catlin from 2011 to 2018.
Richard Sasso, Jr.
LinkedInExperience: Vice President · Berkley Professional Liability (a Berkley Company)
Richard Sasso, Jr. has been Vice President at Berkley Professional Liability (a Berkley Company) since March 2025 and also lists the title Assistant Vice President there since March 2022. At Berkley Professional Liability, Richard Sasso, Jr. was Underwriting Manager from 2020 to 2022 and Senior Underwriter from 2018 to 2020.
Rita Kane
LinkedInExperience: Assistant VP Equine Underwriting · W. R. Berkley Corporation
Rita Kane has been Assistant VP Equine Underwriting at W. R. Berkley Corporation since March 2020, based in the Greater Lexington Area. Rita Kane was Senior Underwriter - Equine Insurance North America, AFIS at AXA XL from 2008 to 2020 and a Licensed Insurance Agent at Muirfield Insurance from 1996 to 2008.
Ryan Munro Oosterheert
LinkedInExperience: Vice President, Corporate Underwriting · W. R. Berkley Corporation
Ryan Munro Oosterheert has been Vice President, Corporate Underwriting at W. R. Berkley Corporation since February 2026. Ryan Munro Oosterheert was Chief Operations Officer, Markel Specialty at Markel from 2023 to 2026, Head of US Strategy at Markel from 2019 to 2022 and Executive Vice President, Eastern Underwriting Center Branch Manager at Chubb from 2017 to 2019.
Tom Woodstock
LinkedInExperience: Vice President · Berkley Specialty Property (a Berkley Company)
Tom Woodstock has been Vice President at Berkley Specialty Property (a Berkley Company) since April 2024 and held the title Vice President of Undwrwriting E&S Commercial Property there from 2024 to 2025. Tom Woodstock was Senior Director - Ocean Marine, Inland Marine and Brokerage Property at Markel from 2020 to 2024 and Regional Vice President at Liberty Specialty Markets from 2010 to 2017.
Choose the right perspective
Match the Berkley operating unit and line in a person's title to the decision you are working through. Weigh whether you need someone from corporate underwriting or someone who leads underwriting inside one specialty unit.
Questions to take into the conversation
- 01What did you focus on first when you took on your underwriting leadership role at your Berkley unit?
- 02How do you set underwriting priorities for the specialty line you lead?
- 03What has your own work at W. R. Berkley taught you about developing underwriters?
Reaching W. R. Berkley underwriting leaders
How can I contact one of these W. R. Berkley underwriting leaders?
Pick one of the 10 people on this page and choose "Book a paid call", or describe your project to find others. You offer a fee for a 15-minute call or a written answer, Instant Expert finds the person's work email and sends the invitation, and they decide whether to accept. The list covers 8 companies, including Key Risk (a Berkley Company), Berkley Small Business Solutions (a Berkley Company) and Berkley Meridian (a Berkley Company), based on profile data retrieved on October 24, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach W. R. Berkley underwriting leaders?
You choose the offer, starting at $5 per person. The offer is what the person receives, and Instant Expert's fee is added on top, so a $100 offer costs you $125. The fee is 20% of what you pay. You're charged only when the person books the call or sends the answer.
What if they don't reply?
You pay nothing. Instant Expert sends follow-up reminders, and if the person hasn't booked or answered within 7 days, the request expires and any hold on your card is released. You can invite several of the 10 people on this list at once and cap your total spend, so you pay only for the ones who accept.
Can an AI agent ask one of these W. R. Berkley underwriting leaders a question?
Yes. An agent with a USDC wallet on Base can ask one question without an Instant Expert account. It names the person, for example by the LinkedIn URL on this page, and pays per ask over x402 (HTTP 402). The person answers in writing or by voice note, and if nobody answers within 7 days, the payment goes back to the wallet automatically. Claude and ChatGPT can do the same through the Instant Expert connector: setup is at /docs/mcp for Claude and /docs/chatgpt for ChatGPT. x402 docs
About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot; roles marked former had ended by then. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.
Request a correction or removal