Transactional Risk Advisors
Transactional Risk Advisors is a specialty insurance brokerage providing Representations and Warranties, Tax Liability, Contingent Liability, Environmental, and Litigation Buy-Out insurance plus due diligence advisory services to private equity sponsors and corporate acquirers in middle-market M&A transactions. Founded 2012, acquired by Oswald Companies in 2016.
- Company typePrivate
- Founded2012
- HeadquartersCleveland, United States
- Headcount11–50
- GTM typeB2B
- OfferingServices
What Transactional Risk Advisors does
Transactional Risk Advisors, LLC (TRA) is a specialty insurance brokerage founded in 2012 in Cleveland, Ohio by Jeff Phillips, a Certified Risk Manager with over 30 years of insurance brokerage experience, and Steven C. Lee, Esq., an M&A attorney and former General Counsel of TravelCenters of America and Valley National Gases with over 30 years of corporate legal experience. The firm focuses exclusively on transactional risk insurance products for middle-market mergers and acquisitions, with deal sizes ranging from $10 million up to $1 billion. In September 2016, TRA was acquired by Oswald Companies, one of the largest independently owned insurance brokerages in the U.S. (founded 1893, employee-owned), and now operates as part of the Unison Risk Advisors network of companies, with its commercial reach expanded nationally in 2024.
TRA's core product portfolio consists of five specialized insurance lines: Representations and Warranties (R&W) Insurance, Tax Liability Insurance, Contingent Liability Insurance, Environmental Insurance, and Litigation Buy-Out Insurance. These are complemented by due diligence services covering insurance programs, employee benefits, and risk management strategies. Pricing is structured on a case-by-case basis; R&W premiums typically range from 2.4% to 2.7% of policy limits with retention of 0.6% to 0.9% of enterprise value, and policies can be issued in as little as 5-7 business days. The firm has no proprietary technology platform — all service delivery is human-advisor-led, leveraging long-term underwriting relationships and the dual legal-insurance backgrounds of its principals.
Revenue is generated through two primary streams: (i) insurance brokerage commissions earned from carriers for placing transactional risk policies, and (ii) professional advisory fees for due diligence services. Go-to-market is exclusively direct sales, with field-based engagement targeting private equity sponsors, strategic corporate acquirers, and their portfolio companies. Demand generation is supported by content marketing and thought-leadership publications on M&A risk topics. Primary customer segments are middle-market companies undergoing M&A and private equity firms seeking to allocate risk in auctions and exits; secondary segments include corporate acquirers pursuing overseas targets with stringent board-level risk requirements.
Transactional Risk Advisors firmographics
Firmographics- Name
- Transactional Risk Advisors
- Legal name
- Transactional Risk Advisors, LLC
- Website
- https://transactionalrisk.com
- Company type
- Private
- Founded year
- 2012
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- Transactional Risk Advisors is a specialty insurance brokerage providing Representations and Warranties, Tax Liability, Contingent Liability, Environmental, and Litigation Buy-Out insurance plus due diligence advisory services to private equity sponsors and corporate acquirers in middle-market M&A transactions. Founded 2012, acquired by Oswald Companies in 2016.
- Ownership category
- akta.pro rank
Transactional Risk Advisors industry classification
Industry- Product category
- Transactional Risk Insurance Brokerage
- NAICS
- Insurance Agencies and Brokerages (52421), Agencies, Brokerages, and Other Insurance Related Activities (5242)
- SIC
- Insurance Agents, Brokers & Service (6411)
- akta.pro primary industry
- Insurance Due Diligence & Transaction Risk Advisory (M&A, W&I) (FSAEADAM)
Keywords
Where Transactional Risk Advisors is headquartered
LocationHeadquarters
- HQ city
- Cleveland
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Transactional Risk Advisors business model
Business model- GTM type
- B2B
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales
Revenue model
- Insurance Brokerage Commissions: TRA earns commissions from insurance carriers for placing transactional risk insurance products including Representations and Warranties, Tax Liability, Environmental, Contingent Liability, and Litigation Buy-Out insurance policies.
- Advisory and Due Diligence Services: Professional advisory services for M&A transactions including due diligence on insurance programs, employee benefits, and risk management strategies for private equity and corporate buyers.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Other | Pay-as-you-go | Representations and Warranties Insurance - approximately 2-5% of limit of liability |
| Other | Pay-as-you-go | R&W Insurance Policy Structure - Limits at 10%-15% of enterprise value |
| Other | Pay-as-you-go | Litigation Buy-Out Insurance - case-by-case pricing |
| Other | Pay-as-you-go | Contingent Liability Insurance - case-by-case pricing |
| Other | Pay-as-you-go | Tax Liability Insurance - case-by-case pricing |
Go-to-market motion2 records
Distribution channels1 record
Marketing channels4 records
Transactional Risk Advisors product offering
Product offeringCore offering
Transactional Risk Advisors (TRA) is a specialty insurance brokerage that places transactional risk insurance products for middle-market mergers and acquisitions, including Representations and Warranties (R&W), Tax Liability, Contingent Liability, Environmental, and Litigation Buy-Out insurance. The firm complements these placements with advisory due diligence services on insurance programs, employee benefits, and risk management for private equity sponsors, strategic acquirers, and their portfolio companies. TRA operates as part of Oswald Companies and Unison Risk Advisors.
Product overview
Transactional Risk Advisors offers a suite of specialized transactional risk insurance products for the mergers and acquisitions community, serving both buyers and sellers. The core portfolio includes Representations and Warranties Insurance (R&W Insurance), Tax Liability Insurance, Contingent Liability Insurance, Environmental Insurance, and Litigation Buy-Out Insurance, all designed to mitigate risk and facilitate deal closings. These products are complemented by Due Diligence Services that assess insurance and employee benefits across industries. The company specializes in middle-market transactions ranging from $10 million to $1 billion, with coverage being flexible and affordable for mergers, acquisitions, divestitures, restructuring, and workouts.
Differentiator
Problem solved
Functional benefit
Products and services
- Representations and Warranties Insurance (R&W Insurance) Breach of contract coverage designed to enhance or replace seller indemnification to buyers in M&A transactions. It covers unforeseen costs arising from breaches of seller representations such as customer contracts, employment breaches, or financial misstatements.
- Tax Liability Insurance Protection against losses incurred when a taxing authority challenges or revokes a previous tax position. Covers federal, state, local, or foreign tax exposure including taxes, interest, fines, penalties, defense costs, and tax gross-up.
- Contingent Liability Insurance Protection against specific and known indemnities within the context of a transaction, covering issues such as specific indemnity obligations, successor liability, contractual issues, governmental approval contingency, and fraudulent conveyance.
- Environmental Insurance Protection against unforeseen damages caused by environmental issues such as pollution or contamination, typically not covered by standard Reps and Warranties insurance. Covers clean-up costs, natural resource damage, bodily harm, and environmentally triggered events.
- Litigation Buy-Out Insurance Coverage for specific lawsuits or known claims that can adversely impact an organization during or after a transaction, enabling transfer of existing third-party liability to an insurer or hedging against future exposures to facilitate deal completion.
- Due Diligence Services Insurance and employee benefits due diligence services across a wide spectrum of industries, leveraging resources to bring competitive strategy and disciplined process to risk management, ensuring pre-closing findings are resolved quickly for efficient post-close transition.
Quantifiable outcome
- R&W Insurance policy issuance can be completed in 2-3 weeks (underwriting process)
- +3 more outcomes
Companies that use Transactional Risk Advisors
Customer profileSegments3 records
Ideal customer profiles3 records
Transactional Risk Advisors technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Transactional Risk Advisors partnerships and signals
Strategic signalPartnerships
One partnership is on record.
- Oswald CompaniescoreOswald Companies, one of the largest independently owned insurance brokerages in the U.S., acquired Transactional Risk Advisors, LLC in September 2016. TRA operates as part of the Oswald Companies network, strengthening their ability to advise clients including private equity and strategic buyers on due diligence and risk mitigation. The acquisition complements Oswald's existing due diligence and aggregation structures.
Scale indicators5 records
Recent moves5 records
Expansion highlights5 records
Transactional Risk Advisors competitors and assessment
Company assessmentBroad incumbents
- Lockton: Largest privately held independent insurance brokerage in the U.S., with M&A and private equity practices placing transactional risk insurance. Comparable to TRA in independent-ownership positioning, with substantially broader geographic and product reach.
- Aon: Global insurance and reinsurance brokerage with a dedicated Transaction Solutions (R&W) practice covering middle-market through large-cap M&A. Competes with TRA on the same product set (R&W, tax, contingent) but at greater scale, with broader carrier panels and international reach.
- Willis Towers Watson (WTW): Global advisory and brokerage firm with a Transactional Liability practice offering R&W, tax, and contingent liability insurance for M&A. Competes in the same middle-market and large-cap segments as TRA and is scaling its M&A specialty brokerage capabilities.
- Hub International: North American insurance brokerage with M&A advisory and private equity practice groups that place R&W and adjacent transactional coverages. Comparable to TRA in middle-market reach and PE sponsor focus, with broader regional scale.
- Marsh: Operating unit of Marsh McLennan; Marsh's M&A Practice and Private Equity/Mergers & Acquisitions Group place R&W and specialty transactional risk insurance globally. Overlaps directly with TRA on R&W, tax, and contingent liability placements, particularly for middle-market sponsors.
- Alliant Insurance Services: Specialty insurance brokerage with M&A and private equity advisory capabilities and growing transactional risk coverage placement. Overlaps with TRA on middle-market R&W and contingent liability work.
Direct peers
- McGill and Partners: Specialty insurance and reinsurance brokerage with a focused M&A / transactional risk practice serving private equity sponsors. Directly comparable to TRA in product set (R&W, tax, contingent) and PE-led middle-market deal orientation.
- Woodruff Sawyer: Mid-market-focused insurance brokerage with a dedicated Transactional Risk practice offering R&W, tax, and contingent liability coverage. Closest size and specialty match to TRA, serving private equity and strategic acquirers in the lower-middle and middle market.
- Risk Strategies Company: National specialty insurance brokerage with a Transactional Risk / M&A practice placing R&W and related coverages. Comparable to TRA in serving middle-market PE and corporate acquirers, with broader specialty product breadth across the U.S.
Regional players
- Tysers: U.K.-headquartered specialty insurance broker with a Transactional Risks team placing R&W insurance for cross-border M&A into the U.S. market. Adjacent comparable to TRA on product set, but primarily competing in cross-border deals with U.K./European sponsors and acquirers.
Market position
Strengths4 records
Weaknesses4 records
Competitive moat3 records
Key risks6 records
Key highlights6 records
Customer concentration
Transactional Risk Advisors compliance and trust
Trust signalCompliance2 records
Transactional Risk Advisors financial estimates
Financial estimateRevenue estimate
Valuation estimate
Transactional Risk Advisors leadership team
Management profileNumber of profiles
Profiles6 records
Transactional Risk Advisors funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Transactional Risk Advisors 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 Transactional Risk Advisors
What does Transactional Risk Advisors do?
Transactional Risk Advisors (TRA) is a specialty insurance brokerage that places transactional risk insurance products for middle-market mergers and acquisitions, including Representations and Warranties (R&W), Tax Liability, Contingent Liability, Environmental, and Litigation Buy-Out insurance. The firm complements these placements with advisory due diligence services on insurance programs, employee benefits, and risk management for private equity sponsors, strategic acquirers, and their portfolio companies. TRA operates as part of Oswald Companies and Unison Risk Advisors.
Is Transactional Risk Advisors a public or private company?
Transactional Risk Advisors is a private company. It is classified as corporate owned and is currently operating.
When was Transactional Risk Advisors founded?
Transactional Risk Advisors was founded in 2012. It employs 11 to 50 people.
Where is Transactional Risk Advisors based?
Transactional Risk Advisors is headquartered in Cleveland, United States, in the North America region.
How does Transactional Risk Advisors make money?
Two revenue lines are on record. Insurance Brokerage Commissions are the primary driver. The others are advisory and Due Diligence Services.
Who are Transactional Risk Advisors's main competitors?
Broad incumbents on record are Lockton, Aon, Willis Towers Watson (WTW), Hub International, Marsh and Alliant Insurance Services. Direct peers are McGill and Partners, Woodruff Sawyer and Risk Strategies Company. Tysers is listed as a regional player.
Does Transactional Risk Advisors have an API?
No public API is recorded for Transactional Risk Advisors.
What industry is Transactional Risk Advisors in?
Transactional Risk Advisors's product category is Transactional Risk Insurance Brokerage. Its primary akta.pro industry code is FSAEADAM, Insurance Due Diligence & Transaction Risk Advisory (M&A, W&I). Its NAICS code is 52421 and its SIC code is 6411.