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Chester Ryan Westfall

Advisor at OSAIC — Medford, OR Crater Lake Hwy

Updated today

Credentials

Series 63, Series 66

Experience

21 years

Location

Medford, OR 97504

OSAIC logo

OSAIC

Institution

Total advisors

7,828

Across 3,559 offices

Clients per advisor

73 Low

Avg AUM per client

$398,336 Typical

HNW client ratio

10% Low

About

Chester Westfall is a financial advisor at Osaic Wealth, Inc. with 21 years of industry experience. He holds Series 63 and Series 66 licenses and has worked previously at firms including LPL Financial, MassMutual Investors Services, MassMutual Life Insurance Company, and MetLife Securities. Outside of his advisory role, he is president of COVERGEAR, LLC, a company involved in the creation and sales of outdoor adventure products, and participates in a family-run solar cleaning business. Osaic Wealth serves a diverse client base including individuals, high-net-worth investors, pension plans, corporations, and charitable organizations through a large network of affiliated advisers and multiple advisory platforms. The firm offers integrated brokerage and investment advisory services, using various asset allocation tools and third-party managers to construct portfolios tailored to client risk tolerance and investment restrictions.

Client services

Based on OSAIC

Financial planning Portfolio management Pension consulting Selection of other advisers Educational seminars or workshops

Expertise

Based on OSAIC

Annuities Wealth management Tax-loss harvesting Private / alternative investments Retirement plans for business owners (SEP, solo 401k)

Occupation focus

Based on OSAIC

Founder/Business Owner Executive

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Fee options

Fixed

Fixed or flat fees for financial planning and consulting services generally range up to $25,000, fixed fees for Non-Discretionary Investment Advisory Services range from $500 - $15,000.

Commissions

Advisory Representatives also receive commissions for brokerage and insurance products sold through Osaic Wealth as a broker-dealer.

Project-based

Hourly fees generally range from $0 - $750 per hour for financial planning and consulting, and $50 - $750 per hour for Non-Discretionary Investment Advisory Services.

Other

Account minimum: $5,500 Fee-only: Hourly fees for financial planning or consulting services generally range from $0 - $750 per hour, not exceeding $25,000 total fees. Fixed or flat fees for financial planning and consulting generally range up to $25,000, and fixed fees for Non-Discretionary Investment Advisory Services range from $500 - $15,000, hourly fees $50 - $750 per hour.

Location

See office

Medford, OR Crater Lake Hwy

3369 Crater Lake Hwy, Suite 101

Medford OR 97504

Advisors at this office

3

Most active in

Oregon

Work history

21 years of industry experience

Osaic Wealth

2025 - Present • 1 year

Medford, OR

LPL Financial

2021 - 2025 • 4 years

Medford, OR

Mass Mutual Investors Services

2017 - 2021 • 4 years

Medford, OR

MassMutual life Insurance Company

2016 - 2021 • 5 years

Medford, OR

MetLife Securities

2016 - 2017 • 1 year

Medford, OR

Disclosures

Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.

Business activities & affiliations

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Michael P

Series 66

Central Point, OR

Penfield Investments LLC

Michael Penfield is the sole advisor at Penfield Investments LLC in Central Point, OR, holding a Series 66 designation with 17 years of industry experience. His background includes three years at Edward Jones and twelve years at FanDistro prior to founding Penfield Investments in 2022. In addition to advisory work, he dedicates part of his time to insurance product sales. Penfield Investments LLC provides asset management and financial planning services primarily to individual and high-net-worth clients, managing approximately $4.87 million in non-discretionary assets. The firm utilizes fundamental, technical, and charting analysis, manages held-away retirement accounts through a third-party platform, and integrates an affiliated insurance business.

Cash flow / budgeting Debt management
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Michael H

Series 66

Ashland, OR

True Purpose Advisors, LLC

Michael Hansen is the sole advisor at True Purpose Advisors, LLC in Ashland, Oregon, with 13 years of industry experience. He holds a Series 66 designation and previously worked at Retirement Asset Managers, Inc. from 2017 to 2018. In addition to his advisory role, Hansen operates a business consulting firm, ProfitMax Professionals, LLC, where he serves as Managing Member. True Purpose Advisors serves individuals, high-net-worth clients, business owners, and various business entities by offering cashflow management coaching, insurance and protection analysis, and asset allocation advice. The firm utilizes a client questionnaire to assign accounts to model portfolios managed through a co-advisory relationship with Matson Money, which handles trading and portfolio management.

Cash flow / budgeting Life insurance needs analysis Disability insurance Founder/Business Owner
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Stephen G

Series 63, Series 65

Central Point, OR

Gerritz Wealth Management, Inc.

Stephen Gerritz is the sole advisor at Gerritz Wealth Management, Inc. in Central Point, Oregon, holding Series 63 and Series 65 licenses with 15 years of industry experience. He has operated his independent advisory firm since 1999. Gerritz Wealth Management provides active portfolio management and advisory services to individuals, high-net-worth clients, and profit-sharing plans. The firm employs a tactical asset allocation strategy that integrates fundamental and technical analysis using proprietary timing tools to manage discretionary portfolios.

Active portfolio management Wealth management
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Richard S

Ashland, OR

Schultz and Associates Inc.

Richard Schultz is the sole advisor at Schultz and Associates Inc. in Ashland, OR, with 22 years of industry experience. He has been with Schultz and Associates since 1981. Outside of his advisory work, he owns and operates Kitchen Creek Vineyards. Schultz and Associates provides discretionary portfolio management primarily for individual clients and a small number of pension or profit-sharing plans, focusing on liquid asset management. The firm employs a research-based, top-down approach emphasizing exchange-traded funds, closed-end funds, and short-term Treasury instruments, while maintaining detailed operational controls and customized account management.

Wealth management
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Cassandra D

CFP®

Ashland, OR

Nagel & Padilla, LLC

Cassandra Dexter is a CFP® professional with 12 years at Nagel & Padilla, LLC and five years of industry experience. She has worked exclusively with the firm since 2014 in Ashland, OR. Nagel & Padilla, LLC provides accounting, tax, payroll, bookkeeping, and business consulting services alongside financial planning and investment advisory for individuals, trusts, estates, charitable organizations, and small businesses. The firm emphasizes written financial plans and client communication while not acting as custodian of assets or engaging in discretionary trading.

General tax planning General retirement planning Cash flow / budgeting
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Audrey C

Series 63, Series 65

Medford, OR

Oregon Pacific Wealth Management

Audrey Creak is a financial advisor at Oregon Pacific Wealth Management with 22 years of industry experience. She holds Series 63 and Series 65 licenses and has worked at Oregon Pacific Wealth Management since 2016. Her prior experience includes roles at Oregon Pacific Banking Company and LPL Financial LLC. Oregon Pacific Wealth Management serves individuals, including high-net-worth clients, as well as pension and profit-sharing plans, trusts, estates, and business entities. The firm manages approximately $175 million in assets and constructs globally diversified, risk-based portfolios, primarily using ETFs and mutual funds, with a variety of analytical approaches and options for active management during volatile markets.

Wealth management Passive / index investing Active portfolio management Retirement income strategy General tax planning
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