O'Toole Strategic Investments LLC
Data sourced from SEC public records (and other sources when available). Refreshed weekly • Updated today.
About
O’Toole Strategic Investments LLC serves individual clients — including those characterized as high net worth — by providing investment advisory referrals and client liaison services rather than running discretionary portfolios. The firm’s deliverables focus on identifying and onboarding a third‑party manager for a client’s account, assisting with paperwork, and monitoring the manager’s performance and reporting.
The firm’s process begins with gathering a client’s financial information and suitability factors, then recommending a third‑party manager and monitoring that manager on an ongoing basis; clients receive account statements and are billed directly by the third‑party manager. O’Toole Strategic Investments does not custody or directly manage client assets, and it receives an ongoing portion of advisory fees from the third‑party manager as a referral fee rather than charging its own direct asset‑based management fee.
What is distinctive about the firm is its close affiliation with an insurance business: the owners are licensed insurance agents and devote a material portion of their time to selling insurance products, a practice disclosed as a potential conflict of interest. The firm also primarily operates by recommending a single third‑party manager and explicitly does not vote client proxies or provide direct portfolio management or custody, which differs from many supported advisers that offer in‑house portfolio management and direct AUM billing.
Client services
Expertise
Fee options
Client Directed Accounts charged a flat $300 annual fee
Investment Advisor Representatives are licensed insurance agents and receive commissions on insurance products sold
Account minimum: Determined by the Third-Party Managers (TPMs) to whom OSI refers its Clients; no specific dollar amount stated Minimum fee: $300 flat fee for Client Directed Accounts Fee-only: Fees are paid as a portion of the TPM's advisory fees; OSI receives 1.00% annually of assets under management as referral fees from TPM fees (varies by portfolio type)
Main office
900 Fox Valley Drive, Suite 206
Longwood FL 32779
Advisors at this office
2
Most active in
Florida
Disclosures
Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.
Business activities & affiliations
Is active or affiliated with:
Insurance agent
They sell insurance products and may earn commissions on those sales.
Is not active or affiliated with:
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Broker-dealer / trader
They provide brokerage services and may earn transaction-based compensation in addition to advisory fees.
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Bank
They're affiliated with a bank that may offer its own financial products and services.
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Trust company
They provide trust and estate administration services, typically for separate fees.
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Fund sponsor
They manage or sponsor investment funds and may earn management or performance-based fees if clients invest in them.
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Accountant / CPA / tax prep
They offer tax and accounting services, typically for separate fees.
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Lawyer
They provide legal services, typically billed separately.
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Real estate agent
They facilitate real estate transactions and may earn commissions.
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Other specialized services
They may provide services such as pension consulting or municipal advisory work, typically for separate fees.
Forms ADV
Advisors at this firm
Sean O
Series 63, Series 65
Longwood, FL
O'Toole Strategic Investments LLC
Sean O’Toole is a financial advisor with O’Toole Strategic Investments LLC, holding Series 63 and Series 65 licenses and having four years of industry experience. He has been involved with The O’Toole Group since 2011, where he is also a licensed insurance agent and broker. O’Toole Strategic Investments LLC serves individual clients, including high net worth individuals, by providing investment advisory referrals and client liaison services rather than managing discretionary portfolios. The firm focuses on recommending third‑party managers, assisting with onboarding and paperwork, and monitoring performance, without directly managing client assets.
Caitlin O
Series 65
Longwood, FL
O'Toole Strategic Investments LLC
Caitlin O’Toole is a Series 65-licensed financial advisor with six years of experience, currently with O’Toole Strategic Investments LLC and The O’Toole Group. She has prior work experience at Wekiva Elementary School. Caitlin is also a licensed insurance agent involved with insurance sales and service outside of her advisory work. O’Toole Strategic Investments LLC serves individual clients, including high net worth individuals, by providing investment advisory referrals and client liaison services rather than managing portfolios directly. The firm focuses on recommending and monitoring third-party managers without custody of client assets.
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