Ryan Oates, CFP®, MBA, CPFA

Managing Partner

As a founding member of Water Street Financial, I focus on working closely with high net worth financial planning clients, the growth and expansion of our firm, and work with Tommy to oversee the firm’s retirement plan division.

Because of my passion for what I do, I’ve spent my entire career in the financial services industry. Before founding Water Street Financial, I spent over 5 years with First Bank Wealth Management along with my partner, Chris Cotterell. During our time at First Bank, Chris and I worked together to grow the private client segment of the division and expand the bank’s offering to its clients.

I earned my bachelor’s degree in finance from George Mason University in 2002 and my MBA from Shenandoah University in 2017. I obtained the CFP® designation in 2020 to enhance my focus on providing exceptional financial planning to my clients. I’m also a Certified Plan Fiduciary Advisor (CPFA) meaning that I am targeted towards providing fiduciary advice to retirement plan clients. I also hold FINRA series 7 and 66 licenses through LPL Financial along with life and health insurance licenses.

Outside of the office, you can usually find me at the golf course or enjoying outdoor activities with my wife Raychel and our son, Tyler. My passion is to travel and I especially love traveling to play golf around the world. I most recently went to Scotland and Ireland and am planning to go back again soon.

Chris Cotterell

Managing Partner

As a founding member of Water Street Financial, I’m responsible for investment strategies and portfolio construction, as well as working with individual clients and overseeing the individual client side of the firm.

I have gained over 25 years of experience in the financial services industry, and I started by spending over 8 years working at First Bank Wealth Management along with my partner, Ryan Oates. I worked with Ryan to expand both the private client segment of the division and the bank’s offering to its clients.

In 1989, I received my bachelor’s degree of science from Slippery Rock University. I hold the designation of Certified Funds Specialist along with the Series 7, 63, 66, 9 and 10 securities licenses through LPL Financial and life and health insurance licenses as well.

In my free time, I enjoy spending time with my wife Julie and our daughter, Peyton. I’m also on the Board of Directors for Our Health.

Angela Morrison

V.P. of Operations

As the V.P. of Operations here at Water Street Financial I strive to make our process with clients as seamless as possible. Day to day, I work on managing operations, onboarding new employees and developing and maintaining procedures to ensure a positive client experience, combining best practices and available technology. I’m also responsible for implementing and sustaining compliance procedures and training and supervising administrative staff.

I have almost 20 years of experience in the financial services industry. Before joining the Water Street Financial team in 2016, I spent 8 years with First Bank Wealth Management, along with Chris Cotterell and Ryan Oates. I actually worked with Chris Cotterell at another local investment firm as well, prior to joining First Financial Advisors of First Bank.

In my free time, I enjoy being with my family, cooking, watching old movies and am also an avid fan of Lucille Ball.

Jeff Reid, CFP®

Director of Wealth Management & Financial Planning

Financial planning for you is at the core of what I do as the Director of Wealth Management. My position also focuses on the future growth and expansion of our firm while also overseeing the entire financial planning division.

I’ve spent the past 18 years in the financial services industry, with over 10 years of experience with Schwab and Scottrade prior to joining Water Street Financial. Most recently, I worked as a manager of financial planning with an advisory firm in Colorado.

In 2002, I earned my bachelor of arts degree in economics from Colorado College. I later obtained the CFP® designation in 2010. I hold FINRA series 7 and 66 licenses through LPL Financial as well as life and variable insurance licenses.

In my free time, you can find me taking part in family activities, camping, golfing, one-wheeling and doing my best to add more to the world than I take.

Thomas Stine, CFP®

Director of Retirement Plan Services

I take pride in the work I do with our financial planning clients, as I help them to live their best possible life with their current means. I also work with retirement plan sponsors to navigate complex rules, regulations and laws of ERISA and the DOL in designing plans, including participant financial wellness.

My designations include the CERTIFIED FINANCIAL PLANNER™ professional (CFP®) designation, the Accredited Investment Fiduciary® (AIF®) professional designation and the Profession Plan Consultant™ (PPC™) designation, which signifies a commitment to education and service excellence in the qualified plan industry. I also graduated from the 401(k) Service Training Program™ which addresses the service standards in the retirement plan industry and imparts professionals not only with the knowledge, but the tools needed to meet and exceed those standards. Lastly, I achieved The Certified Plan Fiduciary Advisor (CPFA) credential from The National Association of Plan Advisors, an affiliate organization of the American Retirement Association. The CPFA was developed by some of the nation’s leading advisors and retirement plan experts and demonstrates knowledge, expertise and commitment to working with retirement plans.

My wife, Tina, and I are active and lifelong members in the Winchester Community. I volunteer my time with many causes and hold a position as a senior board member of the Judges Athletic Association. I’m also an avid supporter of my college alma mater, James Madison University.

Tommy Stine is solely an investment advisor representative of Water Street Financial, and not affiliated with LPL Financial. Any opinions or views expressed by Water Street Financial are his/her own and are not those of LPL Financial.

Corbin Sutton, CFP®, MBA

Wealth Manager

As a Wealth Manager, I spend my time creating and maintaining financial plans as well as developing ways to secure the future growth and expansion of the firm. However, my primary focus is working with individual clients.

I’ve spent the past four years in the financial services industry. Prior to joining Water Street Financial, I worked with Sterling Financial Partners, Inc. in Ashburn, VA for over two years, I focused primarily on financial planning and client service during my time there.

I received my MBA from Shenandoah University in 2018 and my bachelor of arts degree in psychology from DePauw University in 2001. During my time at DePauw, I played NCAA college soccer and served as a team captain during my senior year. I now hold FINRA series 7 and 66 licenses through LPL Financial as well as Virginia Life, Health, and Variable Insurance licenses.

I love to travel internationally and spend time outdoors, camping and hiking. I’m also a devoted Oklahoma Sooners football fan.

Caleb Fry

Financial Planner

Caleb graduated from the University of Akron in 2021 with a Bachelor’s in Financial Planning. Over the course of his college career, he had the opportunity to intern with various financial organizations in the corporate and personal wealth planning fields. Following graduation, Caleb gained valuable planning experience with another firm before accepting an offer with Water Street Financial. He holds a FINRA Series 7 through LPL Financial and Series 66 license through Water Street Financial, as well as a Life and Health Insurance license.

In his free time, Caleb enjoys running, reading, and staying active with friends. Being relatively new to Virginia, Caleb and his wife are frequently exploring new activities in the area. He is very excited to join the team at Water Street Financial and adding value wherever he can. Planning for families and individuals is something that Caleb thoroughly enjoys and believes Water Street Financial provides a great opportunity to do just that.

Dru Dearing

Client Relations Associate

As Client Relations Associate, I’m responsible for supporting clients through every stage at our firm. From account opening and maintenance to scheduling client meetings, I strive to make our clients feel as comfortable and informed as possible. Internally, I also maintain our contact relationship management software and assist with event planning and implementation.

I joined Water Street Financial in June of 2016. My experience with account opening and account maintenance allows me to prioritize an abundance of tasks at the office. Everyday, I’m able to gain knowledge in a variety of financial disciplines to add onto my skills in organization, prioritizing and multitasking.

In my free time, I enjoy spending time with family and friends, trying out new restaurants, and I vacation in Florida every chance I get. I graduated from John Handley High school in 2013 and am a lifelong resident of Winchester.