Investing Activities Cash used in investing activities was $77.1 million during the year ended December 31, 2021 , primarily attributable to $75.2 million of cash paid (net of cash acquired) to acquire Wisely and $1.8 million for the development of internal software and purchases of computer and office equipment to support further product development and to expand our employee base to support our operations. Cash used in investing activities was $1.3 million during the year ended December 31, 2020 , primarily due to development of internal software and purchases of computer and office equipment, furniture and fixtures, and leasehold improvements to support further product development and to expand our corporate office. Financing Activities Cash provided by financing activities was $499.5 million during the year ended December 31, 2021 , reflecting $485.5 million of net proceeds from the issuance of Class A common stock in our IPO (net of underwriters’ discounts and commissions), $17.8 million of net proceeds from the exercise of stock options and employee stock purchase plan, and $0.4 million of net proceeds from the exercise of warrants. These increases were partially offset by the payment of deferred offering costs of $4.1 million during the year ended December 31, 2021 . Cash provided by financing activities was $45.3 million during the year ended December 31, 2020 , primarily related to $50.0 million in proceeds from the issuance of our redeemable convertible preferred stock, net of cost, and $2.6 million of net proceeds from the exercise of stock options, partially offset by $3.5 million net repayment of proceeds borrowed in March 2020 under the Amended Loan Agreement, $2.2 million of payments for offering costs related to our IPO, and $1.4 million for payment of employee taxes related to stock option net exercise. Certain Non-GAAP Financial Measures We report our financial results in accordance with generally accepted accounting principles in the United States, or GAAP. To supplement our financial statements, we provide investors with non-GAAP operating income (loss) and free cash flow, each of which is a non-GAAP financial measure. We use these non-GAAP financial measures, in conjunction with financial measures prepared in accordance with GAAP for planning purposes, including in the preparation of our annual operating budget, as a measure of our core operating results and the effectiveness of our business strategy, and in evaluating our financial performance. These measures provide consistency and comparability with past financial performance as measured by such non-GAAP figures, facilitate period-to- period comparisons of core operating results, and assist shareholders in better evaluating us against our peer group by presenting period-over-period operating results without the effect of certain charges or benefits that may not be consistent or comparable across periods or across our peer group. We adjust our GAAP financial measures for the following items to calculate non-GAAP operating income (loss): stock-based compensation expense (non-cash expense calculated by companies using a variety of valuation methodologies and subjective assumptions), equity expense related to charitable contributions, internally developed software amortization (non- cash expense) and transaction costs. Management believes that it is useful to exclude certain non-cash charges and non-core operational charges from non-GAAP operating income (loss) because (1) the amount of such expenses in any specific period may not directly correlate to the underlying performance of our business operations; and (2) such expenses can vary significantly between periods as a result of the timing of new stock-based awards. Free cash flow represents net cash provided by operating activities, reduced by purchases of property and equipment and capitalization of internally developed software. Free cash flow is a measure used by management to understand and evaluate our liquidity and to generate future operating plans. The reduction of capital expenditures facilitates comparisons of our liquidity on a period-to-period basis and excludes items that we do not consider to be indicative of our liquidity. In addition, we believe providing free cash flow provides useful information to investors and others in understanding and evaluating the strength of our liquidity and future ability to generate cash that can be used for strategic opportunities or investing in our business from the perspective of our management and Board of Directors. Our use of non-GAAP financial measures has limitations as an analytical tool, and these measures should not be considered in isolation or as a substitute for analysis of financial results as reported under GAAP. Because our non-GAAP financial measures are not calculated in accordance with GAAP, they may not necessarily be comparable to similarly titled measures employed by other companies. 64