Taylor Oswald
Taylor Oswald is a Cleveland-based, MBE-certified insurance brokerage and risk advisory firm serving middle-market and large corporate clients across nine verticals plus high-net-worth individuals, operating as a minority-owned entity within the Unison Risk Advisors platform.
- Company typePrivate
- Founded2011
- HeadquartersCleveland, United States
- Headcount11–50
- GTM typeB2B
- OfferingServices
What Taylor Oswald does
Taylor Oswald is a Cleveland, Ohio-based insurance brokerage and risk advisory firm founded in 2011 as a joint venture between Oswald Companies and entrepreneur Eddie Taylor, operating today as a minority-owned constituent entity of Unison Risk Advisors Inc. — a platform formed in 2020 through the merger of Oswald Companies and RCM&D with more than 900 employee-owners across 20 offices in the Mid-Atlantic, Midwest, and Southeast. The firm serves middle-market and large corporate clients across nine declared verticals (construction and real estate, healthcare systems, public entities, non-profits and education, manufacturing, service and financial institutions, retail, warehousing/distribution/transportation) plus a high-net-worth personal risk segment, delivering an integrated portfolio that spans Property & Casualty, Employee Benefits (including a Wellness+ add-on), Retirement Plan Services, Personal and Family Risk Management, Life Insurance and Wealth Preservation, and Workers' Compensation (including Ohio BWC Group Rating advocacy that can lower employer premiums by up to 53%).
The company does not operate proprietary technology platforms; service delivery is broker-led and relationship-based, with quarterly reviews, annual renewals projected 5–6 months in advance, in-house claims advocacy, and global reach extended through the Assurex Global partnership network. Specialized coverage offerings — Active Assailant, Cyber Liability, Directors and Officers, Disability, Child Sexual Abuse Prevention, and Group Personal Excess Liability — complement the core lines and are positioned around emerging risk themes (cybercrime, active assailant, governance liability).
Taylor Oswald generates revenue through commissions earned on placed insurance premiums across its commercial and personal lines, with annual billing cycles and quote-based pricing that varies by client risk profile, industry, claims history, and carrier underwriting. Distribution combines enterprise field sales for the mid-market and large-corporate segment with inside sales, website contact forms, and an educational webinar/content marketing engine (AI Cybercrime, Employee Benefits Landscape, D&O, Group Rating) that supports top- and mid-funnel demand generation. The firm holds Ohio Certified MBE status, has been externally validated through Crain's Cleveland Notable Black Leaders (2024), BBB Champion of Integrity (2024), and Leadership Cleveland Class of 2026, and functions as a regional flagship for minority-owned insurance distribution within the Unison Risk Advisors ecosystem.
Taylor Oswald firmographics
Firmographics- Name
- Taylor Oswald
- Legal name
- Taylor Oswald LLC
- Website
- https://tayloroswald.com
- Company type
- Private
- Founded year
- 2011
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- Taylor Oswald is a Cleveland-based, MBE-certified insurance brokerage and risk advisory firm serving middle-market and large corporate clients across nine verticals plus high-net-worth individuals, operating as a minority-owned entity within the Unison Risk Advisors platform.
- Ownership category
- akta.pro rank
Taylor Oswald industry classification
Industry- Product category
- Insurance Brokerage
- NAICS
- Insurance Agencies and Brokerages (524210)
- SIC
- Insurance Agents, Brokers & Service (6411)
- akta.pro primary industry
- Specialty Insurance Brokerage (Marine, Aviation, Cyber, Professional Lines) (FSAEADAJ)
- akta.pro secondary industries
- Wholesale Insurance Brokerage (Excess & Surplus Lines) (FSAEADAD), Directors & Officers (D&O) Liability (FSAJADAF), Management Liability (D&O/EPL/Fiduciary) (FSAJAGAD), Professional Liability (E&O) (FSAJAGAC), Risk Management & Insurance Advisory for Families (FSAAADAK)
Keywords
Where Taylor Oswald is headquartered
LocationHeadquarters
- HQ city
- Cleveland
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Taylor Oswald business model
Business model- GTM type
- B2B
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D, Others
Revenue model
- Insurance Brokerage Commissions: Taylor Oswald generates revenue through commissions earned from placing insurance policies on behalf of clients with insurance carriers. Commissions are typically a percentage of the premium paid by clients. The company offers Property & Casualty, Employee Benefits, Retirement Plan Services, Life Insurance, Workers' Compensation, and Personal & Family Risk Management services.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Annual | Quote-based insurance brokerage services |
Go-to-market motion3 records
Distribution channels4 records
Marketing channels5 records
Taylor Oswald product offering
Product offeringCore offering
Taylor Oswald is a full-service insurance brokerage and risk advisory firm that places commercial and personal insurance coverage on behalf of clients and earns commissions from carriers. Its core service portfolio spans Property & Casualty, Employee Benefits, Retirement Plan Services, Life Insurance & Wealth Preservation, Workers' Compensation, and Personal & Family Risk Management, supplemented by specialized coverages such as Cyber Liability, D&O, Active Assailant, Disability, and Child Sexual Abuse Prevention. Services are delivered through dedicated risk advisors, in-house claims advocacy, and carrier relationship management across Ohio and the broader Midwest.
Product overview
Taylor Oswald is a full-service insurance advisory firm offering an integrated portfolio of six core service areas: Property & Casualty Insurance, Employee Benefits (with Wellness+ program), Retirement Plan Services, Personal & Family Risk Management, Life Insurance & Wealth Preservation, and Workers' Compensation (including Third Party Administration). The firm also provides specialized coverage offerings including Active Assailant, Cyber Liability, Directors & Officers (D&O), Disability Insurance, and Child Sexual Abuse Prevention coverage. Services are delivered through strategic partnerships with Oswald Companies (Unison Risk Advisors), Oswald Financial, and the Assurex Global network, enabling global risk management capabilities with personalized local service.
Differentiator
Problem solved
Functional benefit
Products and services
- Property & Casualty Insurance
Quantifiable outcome
- Franchise owner saved $240,000 annually in health insurance premiums while implementing a compliant benefits program
- +1 more outcomes
Companies that use Taylor Oswald
Customer profileNamed customers1 record
Segments10 records
Ideal customer profiles6 records
Taylor Oswald technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Taylor Oswald partnerships and signals
Strategic signalPartnerships
Seven partnerships are on record, tiered flagship, core and minor.
- Unison Risk Advisors Inc.flagshipUnison Risk Advisors Inc. was established in 2020 through the strategic merger of Oswald Companies and RCM&D. Taylor Oswald operates under this umbrella organization, which features more than 900 employee-owners in 20 office locations throughout the Mid-Atlantic, Midwest, and Southeast.
- Oswald CompaniesflagshipFounded in 2011 as a joint venture between Oswald Companies and entrepreneur Eddie Taylor. Taylor Oswald operates as a minority-owned partner organization of Oswald Companies, gaining access to extensive resources, carrier relationships, and operational support while maintaining independent brand identity and market focus.
- Assurex GlobalcoreAssurex Global is the world's largest association of privately held insurance brokers. Taylor Oswald leverages this partnership to provide global resources for effective worldwide risk management, extending their reach beyond regional operations.
- RCM&DcoreRCM&D is a sibling company under Unison Risk Advisors. Taylor Oswald partnered with RCM&D on the AI Cybercrime webinar, providing cyber insurance insight from their sibling organization.
- UR One BenefitsminorUR One Benefits is shown as a partner/affiliate on Taylor Oswald's website footer, indicating a collaborative relationship in the employee benefits space.
- Oswald FinancialminorOswald Financial partners with Taylor Oswald for Retirement Plan Services, collaborating to design strategies and achieve client financial goals.
- Transactional Risk AdvisorsminorTransactional Risk Advisors, A Unison Risk Advisors Company, is shown as a partner/affiliate, indicating collaboration within the Unison network.
Scale indicators4 records
Recent moves8 records
Expansion highlights6 records
Taylor Oswald competitors and assessment
Company assessmentBroad incumbents
- Oswald Companies: Taylor Oswald's founding JV partner and parent organization under Unison Risk Advisors. Operates a much larger commercial brokerage across multiple states, overlapping on P&C, employee benefits, and workers' comp but with a broader portfolio and larger employee base.
- Marsh McLennan: Global incumbent brokerage and risk advisory firm with massive middle-market and large-corporate presence. Competes indirectly for Taylor Oswald's enterprise accounts and sets the carrier-relationship benchmark.
- Aon: Global insurance brokerage and advisory firm with significant middle-market and specialty practice overlap (cyber, D&O, construction). A relevant comparator on scale, carrier access, and benefits brokerage depth.
Direct peers
- RCM&D: Sibling company under Unison Risk Advisors, formed through the 2020 Oswald-RCM&D merger. Offers overlapping commercial insurance, employee benefits, and risk advisory services, frequently co-hosting client webinars with Taylor Oswald.
- Alliant Insurance Services: Large national middle-market commercial insurance brokerage serving specialty and complex-risk accounts across P&C, employee benefits, and surety — directly comparable to Taylor Oswald's core middle-market and large-corporate segments.
- USI Insurance Services: Middle-market and large-account commercial brokerage with deep employee benefits, P&C, and specialty practice groups. Competes for the same middle-market and large corporate buyers Taylor Oswald targets across healthcare, construction, manufacturing, and public sector.
- NFP (an Aon company): Middle-market-focused commercial insurance brokerage and benefits advisor. Comparable in target customer (middle-market companies) and product breadth (P&C, benefits, retirement, personal lines).
- Higginbotham: Independent, employee-owned commercial insurance brokerage with strong middle-market presence in the South and Midwest. Closely comparable employee-ownership model and middle-market commercial focus to Taylor Oswald's positioning.
Emerging players
- Brown & Riding Insurance Services: Specialty wholesale brokerage focused on E&S and complex commercial risks including construction, cyber, and management liability. Comparable to Taylor Oswald's specialty practices that route risk into E&S markets.
Others
- Assurex Global: Global alliance of privately held insurance brokers that Taylor Oswald leverages for worldwide placement. Peer in the sense that other Assurex member firms (regional independents like Holmes & Company, RPS) share Taylor Oswald's boutique-with-global-reach model.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat5 records
Key risks6 records
Key highlights7 records
Customer concentration
Taylor Oswald social profiles
Digital presenceTaylor Oswald financial estimates
Financial estimateRevenue estimate
Valuation estimate
Taylor Oswald leadership team
Management profileNumber of profiles
Profiles7 records
Taylor Oswald funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Taylor Oswald M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Taylor Oswald
What does Taylor Oswald do?
Taylor Oswald is a full-service insurance brokerage and risk advisory firm that places commercial and personal insurance coverage on behalf of clients and earns commissions from carriers. Its core service portfolio spans Property & Casualty, Employee Benefits, Retirement Plan Services, Life Insurance & Wealth Preservation, Workers' Compensation, and Personal & Family Risk Management, supplemented by specialized coverages such as Cyber Liability, D&O, Active Assailant, Disability, and Child Sexual Abuse Prevention. Services are delivered through dedicated risk advisors, in-house claims advocacy, and carrier relationship management across Ohio and the broader Midwest.
Is Taylor Oswald a public or private company?
Taylor Oswald is a private company. It is classified as management employee owned and is currently operating.
When was Taylor Oswald founded?
Taylor Oswald was founded in 2011. It employs 11 to 50 people.
Where is Taylor Oswald based?
Taylor Oswald is headquartered in Cleveland, United States, in the North America region.
How does Taylor Oswald make money?
One revenue line is on record: insurance Brokerage Commissions.
Who are Taylor Oswald's main competitors?
Broad incumbents on record are Oswald Companies, Marsh McLennan and Aon. Direct peers are RCM&D, Alliant Insurance Services, USI Insurance Services, NFP (an Aon company) and Higginbotham. Brown & Riding Insurance Services is listed as an emerging player. Assurex Global is listed as an others.
Does Taylor Oswald have an API?
No public API is recorded for Taylor Oswald.
What industry is Taylor Oswald in?
Taylor Oswald's product category is Insurance Brokerage. Its primary akta.pro industry code is FSAEADAJ, Specialty Insurance Brokerage (Marine, Aviation, Cyber, Professional Lines), with a secondary code of FSAEADAD, Wholesale Insurance Brokerage (Excess & Surplus Lines). Its NAICS code is 524210 and its SIC code is 6411.