Ryan Specialty : Financial Results Presentation FY 2023

INVESTOR PRESENTATION

MARCH 2024

DISCLAIMER

Forward-Looking Statements:

This presentation by Ryan Specialty Holdings, Inc. (the "Company," "we," "us") contains forward-looking statements, within the meaning of the Private Securities Litigation Reform Act of 1995, that involve substantial risks and uncertainties and that reflect the Company's current expectations and projections with respect to, among other things, its plans, objectives, and business. These forward- looking statements may include words such as "anticipate," "estimate," "expect," "project," "plan," "intend," "believe," "may," "will," "should," "can have," "likely" and other words and terms of similar meaning in connection with any discussion of the timing or nature of future operating or financial performance or other events. All forward-looking statements are subject to risks and uncertainties, known and unknown, that may cause actual results to differ materially from those that the Company expected. For more detail on the risk factors that may affect the Company's results, see the section entitled ''Risk Factors'' in our most recent annual report on Form 10-K and quarterly reports on 10-Q filed with the SEC, and in other documents filed with, or furnished to, the SEC. Should one or more of these risks or uncertainties materialize, or should underlying assumptions prove incorrect, actual results may vary materially from those indicated or anticipated by such forward-looking statements. Given these factors, as well as other variables that may affect the Company's operating results, you are cautioned not to place undue reliance on these forward-looking statements, not to assume that past financial performance will be a reliable indicator of future performance, and not to use historical trends to anticipate results or trends in future periods. The forward-looking statements included in this presentation relate only to events as of the date hereof. We do not undertake, and expressly disclaim, any duty or obligation to update publicly any forward-looking statement after the date of this release, whether as a result of new information, future events, changes in assumptions or otherwise.

Market and Industry Data

This presentation includes information concerning economic conditions, the Company's industry, the Company's markets and the Company's competitive position that is based on a variety of sources, including information from independent industry analysts and publications, as well as the Company's own estimates and research. The Company's estimates are derived from publicly available information released by third party sources, as well as data from its internal research, and are based on such data and the Company's knowledge of its industry, which the Company believes to be reasonable. The independent industry publications used in this presentation were not prepared on the Company's behalf. This information involves many assumptions and limitations, and you are cautioned not to give undue weight to these estimates. The Company has not independently verified the accuracy or completeness of the data contained in these industry publications and other publicly available information. Accordingly, we make no representations as to the accuracy or completeness of that data nor do we undertake to update such data after the date of this presentation.

Non-GAAP Measures

This presentation contains the following financial measures: Organic Revenue Growth Rate (or "Organic Growth"), Adjusted EBITDAC, and Adjusted EBITDAC Margin, each of which are not recognized under generally accepted accounting principles ("GAAP") in the United States. The Company believes that non-GAAP financial information, when taken collectively, may be helpful to investors because it provides consistency and comparability with past financial performance and assists in comparisons with other companies, some of which use similar non-GAAP financial information to supplement their GAAP results. The non-GAAP financial information is presented for supplemental informational purposes only, should not be considered a substitute for financial information presented in accordance with GAAP, and may be different from similarly-titlednon-GAAP measures used by other companies. Organic Growth, Adjusted EBITDAC, and Adjusted EBITDAC Margin each have limitations as an analytical tool, respectively, and you should not consider any of these measures either in isolation or as a substitute for other methods of analyzing the results as reported under GAAP. Please see the appendix for a reconciliation of such non-GAAP financial information to the most comparable GAAP measure.

2

OUR FOUNDING THESIS

TREND	#1	TREND	#2	TREND	#3	TREND	#4
Risks are becoming bigger	Retail brokers are getting	Retail broker panel	Delegated authority
and more complex	substantially bigger	consolidation is intensifying	is accelerating

Retail broker

	
Broad panel	Singular
	solution

CARRIERS	UNDERWRITERS
Want more	Want to join
intellectual	entrepreneurial
capital	organizations

There is elevated risk and

a need for

specialized solutions

Bigger retail brokers

require the assistance of bigger wholesale brokers

Retail brokers require

a singular solution

Intellectual capital and

entrepreneurs need

a new home

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WHO WE ARE

We are a rapidly growing provider of specialty products and solutions for insurance brokers, agents and carriers.

For retail insurance brokers, we assist in the placement of complex or otherwise hard-to-place risks.

For insurance carriers, we work with retail and wholesale insurance brokers to source, onboard, underwrite and service these same risks.

2010	2nd	$2.1bn
founded	largest U.S. P&C wholesale	2023
broker / managing underwriter1	total revenue

20.4%15.0%

2023 total	2023 organic
revenue growth	revenue growth2

1 According to premium volume; Source: Business Insurance, company filings	4
2 Non-GAAP measure; Please see the appendix for a reconciliation of organic revenue growth to the most comparable GAAP measure.

DRIVING VALUE BY SECURING COVERAGE FOR COMPLEX SPECIALTY RISKS

Traditional risks	Standard
78%	Insurance Carrier
of the commercial market	(Risk bearing)
(Admitted market)1

Insureds Retail	Bespoke, complex,
or larger risks
Broker	22%
(Commission	of the commercial market
and fee model)	(E&S market)	Wholesale Broker
		Underwriting Manager
		(Commission and fee model)

Specialty

Insurance Carrier

(Risk bearing)

Source: SNL, AM Best September 13, 2023 Market Segment Report; 1 ~22% of Ryan Specialty's business was in the admitted market for the year	5	ended 12/31/2023

78% OF OUR PREMIUMS ARE PLACED IN THE ATTRACTIVE E&S MARKET1

WHAT IS THE E&S MARKET?

Market for highly specialized insurance risks

Freedom of rate and form

Tailor coverage to the needs of insureds

Facilitates coverage which wouldn't be possible otherwise

WHAT IS DRIVING THE E&S MARKET?

Increasing catastrophe losses and risk of climate change

Increasing jury verdicts and social inflation

Proliferation of cyber threats as more business is done online

Emergence of novel health risks

1 For the year ended 12/31/2023	6

TOTAL ADDRESSABLE MARKET IS POISED FOR FURTHER GAINS

E&S PREMIUMS & TOTAL NORTH AMERICA COMMERCIAL P&C PREMIUMS

RYAN Total Addressable Market

($bn)

$149

$12

$137

	Commercial Lines Premium		E&S Premium	$450
					$98	E&S CAGR1
			$356	10.2%
		$292	$66
$258	$41
$33	$235				Admitted Market
$32
				$351	CAGR1
					4.4%
		$251	$290

$224 $203

Underlying E&S Market

• Specialized Admitted Market P&C
• International P&C
• Group Benefits
• Alternative Risk
• Reinsurance Underwriting

	2000	2005	2010	2015	2020	2022
E&S %	8%	13%	14%	14%	19%	22%
of Total

Extensive Market Opportunity

Source: SNL, AM Best September 13, 2023 Market Segment Report.	1 For the period 2000 to 2022.	7

A CLEAR VALUE PROPOSITION

Retail Brokers

Employees

Carriers

 Wholesale brokers are a "force	 Independent wholesalers are a destination	 Carriers rely on wholesale brokers and
multiplier" for retail brokers:	of choice - the most talented professionals	MGAs / MGUs for product expertise and
 Specialized expertise	want to work with:	distribution capabilities:
 More efficient results for their	 All retail brokers, only possible	 Access to >20,000 retail brokers
through independence
clients	 Gain the ability to quickly enter
 Access to industry-leading talent on a	 Platform that provides the highest	new markets on a variable cost
earnings potential	basis
variable cost basis
	 Entrepreneurial culture
Retailers have used wholesalers for	Ryan Specialty had 98%	Quality submissions and underwriting
over 85% of E&S placements	expertise are paramount to
producer retention in 2023
over the last 5 years1	preserving underwriting performance

1 Per AM Best September 13, 2023 Market Segment Report

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WHOLESALE BROKERS & MGUS OFFER A UNIQUE VALUE TO OUR CLIENTS

	Product
	Expertise
MGUs	Industry
Provide
Lasting	Expertise
Solutions
	Wholesale
	Value
Strength of	Proposition
Depth &
Relationships
Breadth of
Drive Client
Platform
Outcomes
	Speed &
	Efficiency

2022 U.S. E&S Distribution of Premiums1

	% of
Channel	premiums	RYAN capabilities
Wholesale agent / broker	42%
without binding authority
Wholesale agent / broker	14%
with binding authority
Program manager and/or	18%
Managing General
Underwriters
Retail agent / broker	16%
Direct procurement / Other	10%

Ryan Specialty can access 74% of ~$98bn market

1 Per AM Best September 13, 2023 Market Segment Report. Figures may not add due to rounding.

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COMPREHENSIVE, FULL SERVICE PRODUCT OFFERING

Wholesale	Binding	Underwriting
Brokerage
Authority
Management
	14%
65%	21%

Brand

Operating

model

Value

proposition

• Distributes a wide range of products from insurance carriers to retail brokers
• Focused, specialized servicing of retail agent's most challenging risks

• Places larger-volume, smaller premium policies efficiently with insurance carriers
• Timely and secure access to insurance carriers through in-house binding arrangements

• Designs, underwrites, binds and administers policies on behalf of carriers
• Provides carriers with effective market expertise in distinct and complex niches

Illustrative coverages

Construction liability Directors and officers Real Estate / Habitational Environmental liability Coastal wind coverage

Manufacturing	Cyber
Start-ups	Renewable energy
Distressed property	Professional liability
Subsidized housing	Transactional liability
Long-haul trucking	Product liability

Note: Specialty mix represents 2023 Net Commissions and Fees	10