Oakstreet Wealth Management

What Oakstreet Wealth Management does

Oakstreet Wealth Management is a privately held, full-service retirement plan solution provider founded in 1988 and headquartered in Houston with an additional office in Chicago. The firm serves plan sponsors (employers) across the United States, delivering integrated retirement plan services including plan design consulting, investment selection and management acting as an ERISA 3(38) fiduciary, complete recordkeeping, plan administration, and compliance testing. Oakstreet employs between 101 and 250 people and is led by CEO Lindsey A. Black. The firm operates on a fee-based advisory model under multi-year contracts with pricing set on a custom quote basis tied to plan size and complexity.

The company's product portfolio is structured around three core service modules. The Investment Management module delivers fiduciary fund selection and monitoring using a proprietary Investment Philosophy Framework that emphasizes cost-efficient index funds alongside actively managed strategies meeting defined quantitative criteria. The Recordkeeping & Administration module covers daily valuation, payroll integration, compliance testing (ADP/ACP, 410(b), 415(c), 401(a)(4), 402(g), Top Heavy), and 5500 filings, delivered through third-party infrastructure partners including Alliance Pension and Tri-ad. The Plan Design Consulting module provides consultative design of plan structures tailored to client demographics and goals. A 9-part Plan Sponsor Video Series serves as an educational resource supporting client acquisition.

Oakstreet's business model is sales-led and consultative, with prospective clients acquired through website quote requests, phone, and email outreach. The firm does not develop proprietary technology and instead leverages custodial and recordkeeping partnerships with Charles Schwab and Fidelity for asset custody and back-office infrastructure. Revenue is derived from advisory and administrative fees charged to plan sponsors; no fee schedules, revenue figures, or AUM are publicly disclosed. The company is bootstrapped and founder/management-owned, with no parent company, institutional investors, or funding rounds identified.

Name

Oakstreet Wealth Management

Legal name

Oakstreet Wealth Management

Website

https://oakstreetwm.com

Company type

Private

Founded year

1988

Operating status

Operating

Headcount range

101–250 employees

Short description

Oakstreet Wealth Management is a privately held, full-service retirement plan solution provider serving US plan sponsors with integrated investment management (ERISA 3(38) fiduciary), recordkeeping, administration, and plan design consulting from offices in Houston and Chicago.

Ownership category

akta.pro rank

Product category

Retirement Plan Services

NAICS

Portfolio Management and Investment Advice (52394), Pension Funds (525110), Securities, Commodity Contracts, and Other Financial Investments and Related Activities (523)

SIC

Investment Advice (6282)

akta.pro primary industry

Employer Retirement Plan Advisory (401(k)/Pension) (FSAEABAE)

akta.pro secondary industries

Insurance-Integrated Wealth Managers (RIA + Insurance Solutions) (FSAAACAI), Retirement & Pension Wealth (401(k)/IRA/SIPP/Superannuation Retail) (FSAAAAAJ), Advisory Portfolio Management (Non-Discretionary) (FSAAABAD)

Keywords

• Retirement plan services
• Investment management
• Plan administration
• Fiduciary advisory
• Recordkeeping services

Headquarters

HQ city

Houston

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Technology or R&D, Marketing or Sales, Others

Revenue model

1. Retirement Plan Advisory and Management Services: Oakstreet provides comprehensive retirement plan services including plan design consulting, investment selection and management, recordkeeping, and plan administration. The company operates as an ERISA 3(38) Investment Advisor, serving as a fiduciary to retirement plans. Revenue is derived from fees for advisory and management services rendered to plan sponsors (employers) and their retirement plans. The specific fee structure is not publicly disclosed; prospective clients must request a quote.

Pricing tiers

Go-to-market motion1 record

Distribution channels2 records

Marketing channels4 records

Core offering

Oakstreet Wealth Management is a full-service retirement plan solution provider delivering plan design consulting, investment selection and management (acting as an ERISA 3(38) Investment Advisor), recordkeeping, and ongoing plan administration and compliance services to business owners and plan sponsors across the United States. The firm operates a holistic model that integrates advisory, investment management, and administration under one roof, supported by back-office partnerships with Alliance Pension, Tri-ad, Charles Schwab, and Fidelity.

Product overview

Oakstreet Wealth Management offers a unified retirement plan solution combining three core service modules: Investment Management (acting as ERISA 3(38) fiduciary advisor with active/passive fund selection), Recordkeeping & Administration (daily valuation, compliance testing, payroll integration), and Plan Design Consulting. The firm distinguishes itself by managing all these functions in-house rather than separating them, providing integrated investment management, advice, recordkeeping, administration and compliance aimed at creating optimal retirement outcomes. They do not offer proprietary funds or sell products, instead providing independent investment advice with focus on cost-efficient index funds. A supplementary educational resource (Plan Sponsor Video Series) supports client understanding of retirement plan responsibilities.

Differentiator

Problem solved

Functional benefit

Products and services

• Investment Management ERISA 3(38) Investment Advisor services including fund selection, monitoring, replacement, and active and passive investment management focused on cost-efficient index funds and custom-tailored portfolio construction based on client objectives. Designed for plan sponsors (employers) seeking fiduciary investment management for their qualified retirement plans.
• Recordkeeping & Administration Comprehensive plan administration including plan document design, employee notices, eligibility determination, quarterly account statements, daily valuation, data management, payroll integration, compliance testing (ADP/ACP, 410(b), 415(c), 401(a)(4), 402(g), Top Heavy), and 5500 filings. Delivered to plan sponsors through third-party infrastructure providers.
• Plan Design Consulting Consultative retirement plan design services that evaluate business needs, workforce demographics, and goals to create customized plan structures that maximize tax savings and retirement outcomes for business owners and their employees.

Quantifiable outcome

• Active investment management approach focused on achieving solid growth of plan assets while keeping costs low

Segments2 records

Ideal customer profiles1 record

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

Four partnerships are on record, tiered supporting.

• Alliance PensionsupportingOthersAlliance Pension provides recordkeeping, administration, compliance, and custodial services for Oakstreet's retirement plan clients. The partnership enables Oakstreet to offer comprehensive back-office infrastructure while focusing on advisory and consulting services.
• Tri-adsupportingOthersTri-ad serves as a service provider for recordkeeping, administration, and compliance services for Oakstreet's retirement plan clients. The partnership supports Oakstreet's holistic service model.
• Charles SchwabsupportingOthersCharles Schwab provides custodial services for retirement plan assets managed through Oakstreet's investment advisory services. The partnership ensures plan assets are held securely with a well-established financial institution.
• FidelitysupportingOthersFidelity provides custodial services for retirement plan assets, supporting Oakstreet's investment management and advisory services. The partnership leverages Fidelity's scale and infrastructure in the retirement plan market.

Scale indicators2 records

Recent moves4 records

Expansion highlights3 records

Direct peers

• SageView Advisory Group: Independent retirement plan and wealth advisory firm acting as 3(38) fiduciary for corporate plan sponsors. Closely comparable to Oakstreet on core fiduciary advisory offering and mid-market employer focus.
• Gregory & Appel: Mid-west focused retirement and wealth management firm providing 3(21)/3(38) advisory, plan design, and administration. Similar in size, geographic footprint (including Chicago presence), and full-service retirement offering to Oakstreet.
• Sentinel Benefits Group: Mid-market retirement plan advisory firm providing 3(38) investment management and administration services to corporate plan sponsors. Directly comparable on scope and customer profile.
• CAPTRUST: One of the largest US independent retirement plan and investment advisory firms serving corporate plan sponsors with full-service plan design, investment management, and consulting. Directly comparable to Oakstreet in product/scope, though substantially larger in AUM and headcount.
• OneDigital: National retirement and benefits advisory firm providing 3(38) investment advisory, plan design, and administration to mid-market and large employers. Compares directly to Oakstreet on integrated retirement services and consultative sales model, though at materially greater scale.

Broad incumbents

• Empower Retirement: One of the largest US retirement plan recordkeepers and 3(38) investment managers serving plan sponsors of all sizes. Sets industry pricing benchmarks and competes head-to-head with Oakstreet on mid-market plan mandates.
• Fidelity Workplace Investing: The retirement plan services arm of Fidelity Investments; offers full-stack retirement plan recordkeeping, administration, custody, and investment management to corporate plans. Serves as both a vendor partner to Oakstreet and the largest scaled incumbent competitor.
• Principal Financial Group Retirement Services: Large diversified financial services firm offering bundled retirement plan recordkeeping, investment management, and administration to employer plans. Competes in same mid-market plan sponsor segment as Oakstreet.
• Vanguard Retirement Plan Access: Vanguard's retirement plan business offering low-cost investment management and recordkeeping to plan sponsors; establishes aggressive fee benchmarks that pressure independent 3(38) advisors like Oakstreet.
• Charles Schwab Retirement Plan Services: Schwab's retirement plan business providing custody, recordkeeping, and administration to employer plans; acts as custodial partner to Oakstreet. Represents both partner and broad incumbent competitor targeting plan sponsors.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat3 records

Key risks6 records

Key highlights7 records

Customer concentration

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Oakstreet Wealth Management