Sterling Oak Advisors logo

Sterling Oak Advisors

Updated today

Client assets under management

$47,500,000

Clients

36

100% high-net worth

Advisors

2

of 2 employees

Firm type

Supported

1-3 advisors or $200M+ in AUM

Clients per advisor

18

Very Low

Average account size

$1,319,444

About

Sterling Oak provides discretionary investment management, financial planning, and retirement plan advisory services to high‑net‑worth individuals and retirement plans. The firm acts as a fiduciary for retirement accounts and frames engagements around ongoing personal contact with clients.

Portfolios are built primarily from dividend‑paying and dividend‑growing blue‑chip stocks and low‑cost ETFs, with a long‑term orientation while allowing shorter‑term trades for rebalancing, tax harvesting, or changing client needs. Sterling Oak employs macroeconomic, fundamental, technical and trend analysis, conducts ongoing monitoring with formal reviews at least annually, and may retain legacy holdings for tax or portfolio‑fit reasons.

The brochure highlights two features that distinguish Sterling Oak from many peers: it offers performance‑based fee arrangements to “Qualified Clients” subject to high‑water mark calculations, and the firm’s principal is a licensed insurance professional who may receive commission‑based compensation for insurance sales. The firm discloses that insurance activities are separate from advisory services and notes the potential conflict of interest this creates.

Client services

Financial planning Portfolio management

Expertise

Wealth management Retirement income strategy

Fee options

Percentage

Up to 2.00% annually, negotiable based on complexity, asset level, and overall relationship

Commissions

Insurance commissions earned by Mr. O’Connor as a licensed insurance professional, separate and in addition to advisory fees

Project-based

Financial planning services at $400/hour, negotiable

Performance-based

Performance-based fees up to 20% of gains for Qualified Clients (minimum $1,000,000 under management or $2,100,000 net worth), subject to high-water mark calculation

Other

Account minimum: $500,000 (can be waived at sole discretion of Advisor) Fee-only: Investment management fees up to 2.00% annually, financial planning hourly fee of $400, retirement plan advisory fees up to 2.00% annually

Main office location

Sterling Oak Advisors

77 Exeter Street, Suite 1603

Boston MA 02116, United States

Number of offices

1

Most active in

Massachusetts

Disclosures

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

Business activities & affiliations

Advisors at this firm

user avatar

Ryan O

Series 65

Boston, MA

Sterling Oak Advisors

Ryan O'Connor is a financial advisor at Sterling Oak Advisors in Boston, MA, with four years of industry experience. He holds a Series 65 designation and has been with Sterling Oak Wealth Advisors since 2020. His prior work includes roles at Eli's on Whitney, Quinnipiac University, The Cottage Wellesley, and Dover-Sherborn Regional High School. Sterling Oak Advisors serves primarily high-net-worth individuals and retirement plans, providing discretionary portfolio management, financial planning, and retirement-plan advisory services. The firm focuses on portfolios concentrated in dividend-paying and dividend-growing blue-chip equities and low-cost ETFs, employing a long-term investment approach supported by various analytical methods.

Wealth management Retirement income strategy
user avatar

Brian O

Series 63, Series 66

Boston, MA

Sterling Oak Advisors

Brian O'Connor is a financial advisor at Sterling Oak Advisors in Boston, MA, with 17 years of industry experience. He holds Series 63 and Series 66 licenses and has been with Sterling Oak Advisors since 2009. O'Connor is also a partner and equity analyst at Sterling Oak Asset Management, a small investment management company specializing in equity portfolio management. Sterling Oak Advisors serves primarily high-net-worth individuals and retirement plans, offering discretionary portfolio management, financial planning, and retirement-plan advisory services. The firm focuses on concentrated portfolios of dividend-paying and dividend-growing blue-chip equities and low-cost ETFs, using a long-term investment approach informed by various analytical methods.

Wealth management Retirement income strategy
Warmer team member

Not sure where to start?

We'll help you think it through – whether you ultimately need an advisor or not.

Call (201) 292-4557

Warmer provides personalized recommendations and introductions to independent fiduciary advisors. We do not supervise advisors, manage or hold assets, guarantee performance, or provide advice about specific investments.

Each advisor listed on our site is an independent fiduciary responsible for their own advice. Warmer may receive fees from advisors for participation or referrals; these fees are paid by advisors and do not affect the fees clients pay for advisory services.

For advisor listings, we rely on sources including public filings and data provided by advisors, and we cannot guarantee that all information is current or accurate. Please review an advisor's Form ADV and do your own diligence before entering into an advisory relationship.

By using our service, you agree to Warmer's Terms of Service and Advisory Agreement and Privacy Policy. Logos provided by Logo.dev

© 2026 Warmer Holdings Inc. ("Warmer")