Who We Are

Meet Our Team

Seasoned and experienced insurance professionals committed to helping your business succeed.

Ron Hoefer

Founder, Chief Visionary & Storyteller
Ron founded Milestone in 1987 with the goal of changing the insurance brokerage model to one where all parties win and partnerships are formed between client and carrier.
As President, John oversees all operations, sales initiatives and is responsible for client satisfaction. John founded the Brewery Insurance Program in 2012 and specializes in Workers’ Compensation insurance.

Warren Weed

Managing Director – P&C Insurance
As Managing Director of P&C Insurance, Warren oversees the strategy and performance of Milestone’s Real Estate and Solar Contractor niches. Warren joined Milestone in 2019.

Rachel Arnold

Senior Account Executive – P&C Insurance
Rachel has over 25 years’ experience in Property & Casualty insurance and joined Milestone in 2019. Rachel manages a diverse book of national accounts and middle market business and specializes in real estate risks.

Rebecca Chatham

Risk Management Consultant – Personal Insurance
With over a decade managing the personal insurance of individuals and families, Rebecca leads our personal lines division. Rebecca joined Milestone in 2022.

David Dittmar

Senior Account Executive – Group Benefits
David joined Milestone in 2021. As Senior Account Executive he leads the services for our self funded and large group clients. David has nearly 25 years experience in Group Benefits.

Judy Heald

VP of Group Benefits
Drawing on over 35 years experience in Group Benefits, Judy leads the strategy, design and negotiation on all self-funded and large group clients. Judy joined Milestone in 2006.

Emily Kauffman

Account Executive – P&C Insurance
As an Account Executive, Emily services middle market clients and spearheads the Brewery Insurance Program. Emily joined Milestone in 2016 and has over a decade of experience in Property & Casualty Insurance.

Catherine Montoya

Senior Account Executive – P&C Insurance
After nearly 20 years in underwriting at major insurance carriers, Catherine joined Milestone in 2000. Catherine leads our Account Executives and services national and middle-market accounts. A well rounded insurance professional, Catherine specializes in complex coverage challenges in the contractor space.

Rachel Padilla

Claims Advocate
Joining Milestone in 2022, Rachel manages our client’s claims to a successful resolution. Rachel previously worked as a claims adjuster at a major insurance carrier.

Vanessa Pena

Account Manager – P&C Insurance
Vanessa joined Milestone in 2022. Vanessa helps ensure the seamless handling of certificate requests, billing matters, policy endorsements and other important client service matters.