
About Water Street
Financial
Since 2016, Water Street Financial has been helping individuals, families, and business owners in Winchester, VA build, preserve, and transfer wealth with personalized strategies and transparent guidance.
Built on Relationships
Water Street Financial was founded in 2016 with a simple belief: financial planning should be personal, transparent, and built around real people — not products. Our Winchester, VA team has grown from that founding principle into one of the Shenandoah Valley’s most trusted financial planning firms.
Led by Managing Partners Ryan Oates, CFP® and Chris Cotterell, CFS®, our team brings deep expertise in financial planning, investment management, tax strategies, retirement planning, and estate planning — all under one roof.

Meet the People Behind Your Plan
Ryan Oates, CFP®, MBA
Managing Partner & Co-Founder
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Chris Cotterell, CFS®
Managing Partner & Co-Founder
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Angela Morrison
Founding Member & VP of Operations
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Thomas E. Stine, CFP®, CEPA®, AIF®, PPC™, CPFA®
Sr. Planning & Wealth Advisor
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Katie Hershey, FPQP®
Paraplanner
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Peyton Cotterell
Communications & PR Assistant
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Staci Nova
Virtual Admin Trainer
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Cerella Layfield
Administrative Assistant – Virtual
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Lindsey Shaver
Administrative Assistant – Virtual
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Ryan Oates, CFP®, MBA
Ryan Oates CFP®, MBA, is a co-founder, Managing Partner and Certified Financial Planner at WSF Wealth with over 20 years of experience helping families and business owners plan for retirement. He specializes in helping affluent families coordinate a complex financial landscape, navigate retirement, make crucial decisions regarding future income and minimize taxes through active tax planning within their portfolios.
Ryan has spent his entire career in the financial services industry. Prior to founding WSF Wealth, he spent over 5 years with First Bank Wealth Management where he partnered with Chris Cotterell to grow the bank’s private client division and expand its wealth management services.
Ryan earned his CFP in 2020. He earned his MBA from Shenandoah University in 2017 and a Bachelor’s Degree in Finance from George Mason University in 2002.
Outside of the office, Ryan enjoys traveling the world with his wife, Raychel, taking his son Tyler hunting and fishing, and playing bucket list golf courses with his friends. He also collects guitars and plays them on a vary amateur level while listening to old vinyl records.
Chris Cotterell, CFS®
Chris Cotterell CFS®, is a co-founder and Managing Partner of WSF Wealth, where he works closely with individuals, families, businesses, and organizations to help them navigate important financial decisions and pursue their long-term goals. With more than 25 years of experience in the financial services industry, Chris has built his career around creating meaningful client relationships and delivering personalized financial guidance.
At WSF Wealth, Chris oversees the firm’s investment strategies and portfolio management process while leading the individual client advisory practice. He is passionate about helping clients develop comprehensive financial plans that align with their values, priorities, and vision for the future.
Before founding WSF Wealth, Chris spent more than eight years with First Bank Wealth Management, where he partnered with Ryan Oates to grow the bank’s private client division and expand its wealth management services. His experience across investment management, financial planning, and client relationship development continues to shape the firm’s commitment to exceptional service and long-term partnership.
Chris earned his Bachelor of Science degree from Slippery Rock University while maintaining a student-athlete career playing water polo and swimming. He holds the Certified Funds Specialist (CFS®) designation. He also maintains Series 7, 63, 66, 9, and 10 securities registrations through LPL Financial, along with Life and Health Insurance licenses.
Outside of work, Chris enjoys spending time with his wife, Julie, and daughter, Peyton. Whether he’s playing a round of golf, relaxing in Ocean City, Maryland, or making memories with family and friends on the boat or on the beach, Chris values the balance between professional success and the people and experiences that matter most.
Angela Morrison
Angela Morrison is a founding member and Vice President of Operations at WSF Wealth, bringing more than 20 years of experience in the financial services industry. In her role, she oversees the firm’s day-to-day operations and ensuring the organization operates efficiently while delivering an exceptional client experience. In this role, she drives operational excellence by developing, implementing, and continuously improving firm-wide processes, procedures, and technology solutions that enhance productivity, consistency, and service quality.
Angela’s responsibilities include onboarding, training, and developing new employees; supervising and supporting administrative staff; establishing and maintaining operational policies and procedures; implementing technology-driven best practices; overseeing compliance-related processes; processing payroll; and partnering with the firm’s human resources vendor to administer and maintain HR policies, procedures, and employment practices. She also works closely with leadership to support strategic initiatives, improve internal operations, and foster a collaborative, high-performing workplace culture.
Prior to WSF Wealth, Angela spent eight years with First Bank Wealth Management alongside fellow founding members Chris Cotterell and Ryan Oates. Before that, she worked for eight years with Chris at another local investment firm, further building the professional foundation and partnerships that ultimately led to the creation of the firm.
Outside of her professional responsibilities, Angela enjoys spending time with her family, fishing, watching classic films, volunteering with Winchester Rescue Mission, and spending time with Zeus, her Border Collie. She is also a devoted fan of Lucille Ball and appreciates the timeless humor and legacy she created.
Tommy Stine
Tommy is a Certified Financial Planner (CFP®), Investment Adviser, licensed Life Insurance Professional, and Certified Exit Planning Advisor (CEPA®) who helps business owners holistically grow their company’s value, plan for succession, and execute profitable, tax-efficient exit strategies. He works closely with successful individuals, families, and business owners to plan for both their present and future, helping them make informed decisions that allow them to live their best lives with the resources they have. Tommy’s approach integrates comprehensive financial planning, investment management, risk management, life insurance planning, business value enhancement, and exit planning to help clients align their personal, business, and legacy goals. He enjoys building lasting relationships with clients and guiding them through life’s financial opportunities and transitions with clarity and confidence.
Tommy and his wife, Tina, are lifelong residents of Winchester and are deeply committed to serving and giving back to the community that has supported them throughout the years. Together, they volunteer their time with numerous local organizations, including Shenandoah Apple Blossom Festival and the Judges Athletic Association, where Tommy has served as Vice President, President, and Senior Board Member for nearly 30 years. Outside of work and community service, Tommy and Tina enjoy spending time with their many friends and traveling, particularly to the coast of South Carolina, where they appreciate the opportunity to relax and recharge.
Katie Hershey
Katie Hershey is a Financial Paraplanner Qualified Professional (FPQP®) at WSF Wealth and has been with the firm for over two years. She works closely with advisors to develop comprehensive financial plans and provide clients with a clear path toward their financial goals. Katie specializes in financial analysis, data gathering and organization, and preparing detailed reports that support personalized planning strategies.
Prior to joining WSF Wealth, Katie built a strong foundation in finance, organized record-keeping, and exceptional client service through her experience in banking and with a government contractor. She brings that attention to detail and commitment to client care to every aspect of the financial planning process.
Outside of work, she enjoys spending time with her family, exploring new places, and creating lasting memories together.
Peyton Cotterell
Peyton joined WSF Wealth in 2026. She supports the firm’s team through a variety of marketing, communications, client service, and administrative initiatives. She assists with social media and website content, marketing materials, client events, and brand communications while helping enhance the firm’s client experience. Peyton is currently pursuing a degree in Business and Public Administration at Pennsylvania State University and is passionate about expanding her knowledge of financial services while gaining hands-on experience in wealth management and strategic communications.
In her free time, Peyton enjoys spending time with family and friends, and repping blue and white any chance she gets.
Cerella Layfield
Cerella brings strong experience in advisor support, workflow management, and team collaboration. She is organized, dependable, and thoughtful in the way she serves advisors. She works well independently while staying connected to the larger team, which makes her a steady and trusted support partner.
Before joining the team, Cerella worked as an administrative assistant for her church and managed the financial and administrative side of two family businesses. She also brings many years of experience in bookkeeping, reporting, scheduling, and administrative organization.
Cerella lives in East Tennessee and enjoys spending time with her three children, their spouses, and her five grandsons. She also enjoys traveling and attending her church.
Lindsey Shaver
Lindsey graduated in 2014 with an Associate’s Degree in Office Administration from Jefferson State Community College. For four years, she worked as an Administrative Assistant for the children’s ministry at her church. She was responsible for the office administration and assisted in event planning, coordination, and leading worship. Lindsey also assisted at camps and ministry outreaches as a staff member. After her tenure with the children’s ministry, she began working in the service industry while living in Jackson Hole, Wyoming.
In 2020, Lindsey began her career in the finance industry as a bank teller where she honed her skills for high quality customer service with integrity and focus on attention to detail. Because of this dedication, she was promoted to a higher position with greater responsibilities.
Life led her to Tennessee where she lives with her husband and young daughter. She loves to explore new places, hike, camp, ski, and do anything outdoors. She values quality time with family and friends.
Staci Nova
Staci is a highly professional and dedicated virtual assistant who joined the team in 2023. She is a proud graduate of the University of Alabama, where she earned a bachelor’s degree in Human Environmental Sciences with a concentration in Human Development and Family Studies. During her academic career, she was recognized for her achievements as a member of the Alpha Lambda Delta and Phi Eta Sigma national honor societies.
With over seven years of experience in customer service and administrative roles, including three years within the finance industry, Staci brings a well-rounded and in-depth understanding of client support. She is proficient in a wide range of custodian platforms, CRM systems, and other industry-specific software. She also has extensive experience navigating firm processes and enhancing operational efficiency by developing and implementing streamlined workflows.
Staci is committed to delivering exceptional service and takes pride in tailoring her support to meet the unique needs of each client. She values building strong, reliable partnerships and consistently strives to contribute to the success of the advisors she supports.
Staci currently resides in Colorado with her husband and their cat. Outside of work, she enjoys cooking, hiking, and spending quality time with her family.
Our Standard Fee Schedule
| Assets Under Management | AUM Fee Percentage |
|---|---|
| First $500,000.00 | 1.25% |
| Next $1.5 million | 1.00% |
| Next $3 million | 0.85% |
| Above $5 million | 0.65% |
Backed by Industry Partners
LPL Financial
Securities offered through LPL Financial. Member FINRA/SIPC.
Wealthcare Advisory
Investment advice through Wealthcare Advisory Partners LLC, a registered investment advisor.
CFP® Certified
Our team holds the CERTIFIED FINANCIAL PLANNER™ designation.
Common Questions by Service
Select a service to see the most common questions we hear.
How much does financial planning cost?
Varies by complexity. We offer transparent fees and discuss all costs upfront during your complimentary consultation.
What is the difference between a planner and advisor?
A planner creates a comprehensive roadmap. An advisor may focus on investments. We provide both under one roof.
Do I need a plan if I already have a 401(k)?
A 401(k) is one piece. A plan coordinates your entire picture so everything works together.
How often should I review my plan?
At least annually, or whenever you experience a major life event.
Is there a minimum investment?
We work with clients at various stages. Schedule a complimentary consultation to discuss.
How are your fees structured?
Full transparency. All fees are disclosed before you commit. Investment advice through Wealthcare Advisory Partners LLC.
Can I keep my current brokerage?
We custody through LPL Financial and Charles Schwab. We help manage any transition.
What makes you different from a robo advisor?
We provide personalized, human led management that accounts for your complete financial picture.
When should I start planning for retirement?
Now, regardless of age. The earlier you start, the more options you have.
How much do I need to retire?
There is no one size fits all number. It depends on lifestyle, healthcare, income sources, and longevity. We model your specific situation.
Should I take Social Security at 62 or wait?
Depends on health, other income, and spousal situation. We run detailed break even analysis.
Can you help with federal retirement?
Absolutely. Deep experience with FERS, CSRS, TSP, FEHB. It is one of our specialties.
Is tax planning the same as tax preparation?
No. Preparation is filing after the year ends. Planning is proactive, year round strategy to minimize liability.
Do you replace my CPA?
No. We work alongside your CPA as a team on strategic planning. If you need one, we can recommend Winchester, VA professionals.
What is a Roth conversion?
Moving money from a traditional pre tax account to a Roth, where it grows and is withdrawn tax free.
Do I need an estate plan if I am not wealthy?
Yes. It is about protecting wishes, family, and keeping decisions out of court.
What is the difference between a will and a trust?
A will goes through probate and is public. A trust bypasses probate, provides privacy and more control.
Does Water Street Financial draft legal documents?
No. That is your attorney’s role. We develop the financial strategy and coordinate with your attorney.
What is wealth management vs. financial planning?
Planning creates the roadmap. Wealth management is the ongoing execution, managing investments, taxes, estate, and insurance together.
How does Water Street Financial get paid?
Full fee transparency. Disclosed before commitment. Investment advice through Wealthcare Advisory Partners LLC.
Can I meet in person?
Yes. 335 Westside Station Drive in Winchester, VA. We also offer virtual meetings.
How much does it cost to set up a 401(k)?
Costs vary by plan size. Many plans qualify for tax credits that offset setup costs.
Am I required to match contributions?
For 401(k), matching is optional but recommended. For SIMPLE IRAs, a match or non elective contribution is required.
Can I switch from my current provider?
Yes. We handle the entire conversion process to make the switch seamless.