The people leading our way.
We’re building the future of insurance, so our clients and communities can thrive. Together, we can all see possible.
Scott M. Wick
Founder, Chairman & Chief Executive Officer
Scott founded Highstreet in June of 2018 with a vision to help create stronger and more resilient communities. Prior to forming Highstreet, Scott was the President of The Fedeli Group in Cleveland, Ohio. Previously, he was the Executive Vice President and Chief Sales Officer of Hub International Midwest in Chicago, Illinois. Scott is a graduate of the University of Wisconsin-Madison and has an M.B.A. from the University of Notre Dame’s Mendoza College of Business.
Executive Leadership
Krae Dutoit
Chief Retail Officer
Krae joined Highstreet in 2021 with a passion for finding and integrating great growth agencies and helping them continue to scale. In addition to being President of the Western U.S., Krae oversees the agencies in the Gulf region.
James Hutchinson
Chief Commercial Officer & President, Specialty
James joined Highstreet in 2022 with a passion for executing on innovative growth and retention strategies. In addition to being President of the Eastern U.S., James oversees the agencies in the Northeast region.
Todd Macumber
Chief Growth Officer
Todd joined Highstreet in March 2026 as Chief Growth Officer. He is focused on business development, industry solutions, loss control and claims management.
Emma Riza
Chief Operating Officer
Emma joined Highstreet in 2021 with a vision to build the best partner agency experience.
Robert Sajdak
Chief Legal & Risk Officer
Robert joined Highstreet in 2022 with a focus on how agencies can grow to support and protect their clients.
Jim Scott
Chief Human Resources Officer
Jim joined Highstreet in 2024 with a commitment to enhancing workplace culture and attracting top talent.
Karl Sherrill
Chief Development Officer
Karl joined Highstreet in 2021 with a passion to enable others to find the best possible version of themselves and to lead conversations that empower organizations to achieve their true potential.
Kristen Stokes
Chief Broking Officer
Kristen joined Highstreet in October 2025 and is focused on growing and deepening Highstreet’s strategic market relationships.
Angela Williams
Chief Brand & Creative Officer
Angela joined Highstreet in 2021 with a vision to deliver a delightful client experience and to position Highstreet for the future.
Avery Zuck
Chief Financial Officer
Avery joined Highstreet in 2024 with a focus on driving sustainable growth.
Our Regional Leaders
West Region
Brian Clifford
President, West Region
In addition to being President of our West Region, where he oversees the agencies and their growth, development and profitability in that geographic area, Brian is National Segment Leader, Executive Risk, responsible for insurance solutions in management, professional and cyber liability.
Great Lakes Region
Michael Haverdink
President, Great Lakes Region
Mike joined Highstreet in 2019 with a vision to improve the insurance industry’s stature as a trusted advisor. He leads our Great Lakes Region and is also the President of Ottawa Kent Insurance where he has operated a successful agency for more than three decades.
Southeast Region
Alyssa Rockwell
President, Southeast Region
Alyssa holds CIC, CRM and PLCS designations and is responsible for growth and profitability in the Southeast region. Additionally, she supports the enterprise as National Segment Leader, Personal Lines.
Industry Solutions
Vincent Stazzone
President, Gulf Region
As President of Industry Solutions, Vince is responsible for the development of our industry strategy and build. He is also President of both Williams & Stazzone Insurance Agency, which specializes in coverage for diverse segments of the automotive industry, and W&S Underwriters.
Northeast Region
Chris Sumnar
President, Northeast Region
Chris Sumnar has more than 20 years of experience in the insurance and risk management industry. He joined Highstreet Insurance Partners in 2021 and currently serves as President of the Northeast Region.
Central Region
John Thompson
President, Central Region
In addition to being President of the Central Region John is the Market Leader for the region, where he assists agency partners with carrier appointments, market placement and maximizing revenue within consolidated carrier agreements.
Partnership Development
Let’s start a conversation.
Our dedicated Mergers & Acquisitions team of seasoned entrepreneurs is always looking for strategically aligned partnership opportunities.
Karl Sherrill
Chief Development Officer
Karl joined Highstreet in 2021 with a passion to enable others to find the best possible version of themselves and to lead conversations that empower organizations to achieve their true potential.
Michael Woodham
Director, Partnership Development & Strategy
Mike is a key point of contact for prospective new Highstreet agency partners and leads the new partner due diligence and closing processes as well as other strategic initiatives.
Forward together.
We’re agents of change. We love to help people pursue life’s opportunities with tenacity and confidence, to create stronger, more resilient communities. We do it for all our futures.
