10 Sentry Insurance underwriting leaders
Scott Miller, President - National Accounts, Transportation & Regional Insurance, is one of these Sentry Insurance underwriting leaders, whose titles name segments such as national accounts, transportation and commercial lines. A reader can learn how underwriting leaders work at Sentry Insurance from people who have held the role.
Professionals to explore
Brad Schneider TRS, AU, AU-M, AINS
LinkedInExperience: Director of Underwriting · Sentry
Brad Schneider has been Director of Underwriting at Sentry since June 2022, and the profile headline reads Director of Underwriting at Sentry Transportation. At Sentry, Brad Schneider was also Underwriting Manager from 2015 to 2022, Senior Underwriter from 2013 to 2015 and Underwriter from 2008 to 2013.
Brett Hoopingarner CPCU, QPFC
LinkedInExperience: National Sales Director - Direct Writer and Life & Annuity · Sentry
Brett Hoopingarner is a former Director of Underwriting - Direct Writer at Sentry, a role held from November 2018 to October 2025, and has been National Sales Director - Direct Writer and Life & Annuity there since October 2025. At Sentry, Brett Hoopingarner was also Division Manager - Direct Writer South in 2018 and Division Manager - SBP East from 2015 to 2018.
Brian Jorgenson
LinkedInExperience: Director of Underwriting - National Accounts · Sentry
Brian Jorgenson has been Director of Underwriting - National Accounts at Sentry since November 2018, based in the Wausau-Stevens Point Area. At Sentry, Brian Jorgenson was also Underwriting Manager, National Accounts from 2012 to 2018 and Underwriting Manager - Transportation from 2008 to 2012, and the profile says they manage a large staff of underwriters.
Dan Clements
LinkedInExperience: Sr. Director of Sales, Underwriting, & Market Development - Transportation · Sentry
Dan Clements has been Sr. Director of Sales, Underwriting, & Market Development - Transportation at Sentry since April 2023 and has also held Sr. Director of Sales & Underwriting - Transportation there since November 2021, based in Stevens Point, Wisconsin. At Sentry, Dan Clements was also Director of Sales from 2015 to 2021.
James Overturf, CPCU
LinkedInExperience: Former Director of Underwriting Audit & Standards - Personal Lines · Sentry
James Overturf is a former Director of Underwriting Audit & Standards - Personal Lines at Sentry, a role held from September 2003 to January 2010. James Overturf was also Director of Product Management and Underwriting Operations at AFR Insurance from 2010 to 2013 and VP Sales and Underwriting at Omaha Property and Casualty Company from 1996 to 2003.
Mike Schimke
LinkedInExperience: AVP Chief Underwriting Officer · Sentry
Mike Schimke has been AVP Chief Underwriting Officer at Sentry since December 2021, based in Stevens Point, Wisconsin. At Sentry, Mike Schimke was also Assistant Vice President Corporate Underwriting from 2016 to 2021, Corporate Underwriting Executive from 2014 to 2021 and Director of Underwriting, Business Products from 2011 to 2013.
Nic Hernandez
LinkedInExperience: Commercial Lines Underwriting Director- Regional · Sentry
Nic Hernandez has been Commercial Lines Underwriting Director- Regional at Sentry since February 2022, based in Mission Viejo, California. Nic Hernandez was Commercial Lines Underwriting Manager at Sentry from 2018 to 2022 and Sr Middle Market Territory Manager - Business Development at Nationwide from 2015 to 2018.
Peter Brown
LinkedInExperience: Director of Underwriting · Sentry
Peter Brown has been Director of Underwriting at Sentry since July 2024, based in San Diego, California, and the profile headline reads Underwriting Director - Regional. Peter Brown was Sr. Underwriting Director at Liberty Mutual Insurance from 2023 to 2024 and Director - Express Underwriting Operations there from 2017 to 2023.
Randy Ramczyk
LinkedInExperience: Director of Underwriting - Transportation · Sentry
Randy Ramczyk has been Director of Underwriting - Transportation at Sentry since June 2005, based in Stevens Point, Wisconsin. Randy Ramczyk was National Account Underwriting Manager at Sentry Insurance from 2000 to 2005 and National Account Underwriter there from 1995 to 2000.
Scott Miller
LinkedInExperience: President - National Accounts, Transportation & Regional Insurance · Sentry
Scott Miller has been President - National Accounts, Transportation & Regional Insurance at Sentry since January 2016, based in Plover Town, Wisconsin. At Sentry Insurance, Scott Miller was also Vice President - National Accounts from 2014 to 2016, Vice President - Transportation from 2012 to 2014 and Director of Underwriting- National Accounts from 2009 to 2012.
Choose the right perspective
Match the segment or region named in a person's title to the risk or decision you are working through. Weigh whether you need someone who sets underwriting direction across the company or a director who runs underwriting for one segment day to day.
Questions to take into the conversation
- 01What did you focus on first when you took on your underwriting leadership role at Sentry?
- 02How do you decide which risks fit the appetite of the segment you lead?
- 03What has your own work taught you about developing underwriters into leaders?
Reaching Sentry Insurance underwriting leaders
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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.