Q4 2022 Shareholder Letter

Exhibit 99.2

February 27, 2023

Fellow Shareholders:

Our business was tested in 2022, in perhaps one of the most difficult operating environments we have faced in our history as a public company. Significantly higher interest rates weighed heavily on mortgage activity while persistent inflationary pressures wrought havoc on virtually all of our insurance carrier partners. Despite those challenges, we believe our performance this past year proves we have built a durable business that can successfully navigate a very difficult economic cycle, while also enabling us to invest for the future.

The diversification of our company combined with a strong balance sheet and prudent expense management produced $84.5 million of Adjusted EBITDA for the year. We were able to achieve this while maintaining investment in our discreet growth initiatives, which we believe have potential to significantly increase the lifetime value of our customers and improve the long-term margin profile of our company.

The fourth quarter was highlighted by the strong performance of our Insurance segment, as the team's focus on maximizing profitability in a depressed revenue environment led to an impressive six point increase in segment margin from the prior quarter. In Consumer, our small business and personal loan products again performed well against the backdrop of a generally tighter lending environment while driving a three point segment margin improvement sequentially. Our Home business was able to capitalize on increased demand for home equity loans, generating revenue that surpassed our purchase and refinance lines combined. The ability to quickly pivot to this evolving business opportunity is a testament to our deep integration with our lending partners. During the quarter we implemented our previously announced expense reduction efforts, and we have additional expense plans ready should business performance fall short of expectations as we progress through the year ahead.

Looking forward the company is energized by the initiatives we are executing on in 2023. Our focus on becoming the premiere digital ally for consumers, to help them win financially, drives much of our day-today work. Today's announced launch of the LendingTree Win Card, our first branded consumer credit offering in partnership with Upgrade, is a perfect example. We spent a significant portion of last year speaking with thousands of consumers, identifying key financial problems that most burdened them. This input led to designing a number of unique features for the Win Card, which offers a cashback incentive tied to regular usage of our MyLendingTree logged-in experience. We look forward to sharing more milestones in coming quarters as we build a destination for our customers to get timely advice on how to improve their financial lives, which is more relevant to them now than ever.

A summary of our fourth quarter results and future outlook follow below.

SUMMARY CONSOLIDATED FINANCIALS

1. Represents the portion of selling and marketing expense attributable to variable costs paid for advertising, direct marketing and related expenses. Excludes overhead, fixed costs and personnel-related expenses.
2. Variable marketing expense, variable marketing margin, variable marketing margin % of revenue, adjusted EBITDA, adjusted EBITDA % of revenue, adjusted net income (loss) and adjusted net income (loss) per share are non-GAAP measures. Please see "LendingTree's Reconciliation of Non-GAAP Measures to GAAP" and "LendingTree's Principles of Financial Reporting" below for more information.

SEGMENT RESULTS

1. The Home segment includes the following products: purchase mortgage, refinance mortgage, home equity loans, and reverse mortgage loans. We ceased offering reverse mortgage loans in Q4 2022.
2. The Consumer segment includes the following products: credit cards, personal loans, small business loans, student loans, auto loans, deposit accounts, and other credit products such as credit repair and debt settlement.
3. The Insurance segment consists of insurance quote products and sales of insurance policies.
4. The Other category primarily includes marketing revenue and related expenses not allocated to a specific segment.
5. Brand marketing expense represents the portion of selling and marketing expense attributable to variable costs paid for advertising, direct marketing and related expenses that are not assignable to the segments' products. This measure excludes overhead, fixed costs and personnel-related expenses.