Third Quarter 2023 Investor Presentation

$590 Million

Gross Written Premiums

as of 9/30/2023

Low-to-Medium Hazard Focus

Shown as a percentage of 9/30/23 in-force premium

Premium Contribution

Specialty

Agents,

Distribution

Partners

Traditional and DTC

Insurance33%

Agents

67%

$722 Million

In-force Premium

at September 30, 2023 (incl. est. audit premium)

126,120 in-force policies $5,725 average policy size

Nationwide Platform

Over 100-year operating history

Strong underwriting focus with established presence in attractive markets

Record number of policies in-force, excellent operating ratios

Unique, long-standing strategic distribution relationships

Conservative risk profile and prudent capital management

Solid financial position and strong balance sheet

UNIQUE GROWTH DRIVERS SPECIFIC TO EMPLOYERS

Transforming how small businesses and insurance agents utilize digital capabilities to improve their customer experience

1. enhancing the agent experience and agent
   efficiency
   (ii) providing direct-to-

customer workers'

compensation insurance policies through our Cerity brand, which was developed to meet the needs of small businesses seeking an online experience

Classes of Business

We establish and maintain strong, long-term relationships with our vetted and appointed traditional insurance agencies that actively market our products and services. We offer ease of doing business, provide responsive service, and pay competitive commissions. Our sales representatives and underwriters work closely with these agencies to market and underwrite our business. This results in enhanced understanding of the businesses, the risks we underwrite, and the needs of prospective customers. We do not delegate underwriting authority to agents or brokers.

We had approximately 2,523 traditional insurance agencies that marketed and sold our insurance products at December 31, 2022.

We have developed and continue to add other important and emerging distribution channels for our products and services including payroll companies, and health care and property and casualty insurers, as well as digital agents and marketplaces.

A meaningful concentration of our business is being generated by our specialty agent Automatic Data Processing, Inc. (ADP). As part of its services, ADP sells our workers' compensation insurance product along with its payroll and accounting services through its insurance agency and field sales staff. ADP generated 15% of our ending 2022 in-force premiums.

Our digital distribution channel utilizes proprietary application programming interfaces (APIs) to submit, quote and bind applications for workers' compensation insurance. Digital agents generated 5% of our ending 2022 in- force premiums.

To address the changing buying behaviors of small and micro-businesses, we launched Cerity, which offers digital insurance solutions, including direct-to-customer workers' compensation coverage.

Cerity specializes in smaller risks in those classes of business where we believe that customers prefer an online experience and offers a digital and mobile-friendly experience that allows small businesses to easily acquire and maintain their policies.

Price-to-book Ratio

3.00

100% Workers' Comp Focused on lowand midhazard accounts

100% Workers' Comp

Focused on highhazard accounts

$ in millions

Market Conditions

Q3 2023 Update

Reached a record-level of 126,120 policies in-force

# of policies