This Report contains forward-looking statements that involve risks and uncertainties. The statements contained in this Report that are not purely historical are forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934, including but not limited to our statements about the anticipated growth and development of our businesses and financial results, including profitability, cash flows, liquidity, and capital allocation; the expected effects of our cost reductions and recent restructuring, including future cost savings and restructuring charges; the expected impacts of our mass customization platform; the expected effects of mid- and upper-funnel advertising in Vista; sufficiency of our liquidity position; legal proceedings; and sufficiency of our tax reserves and expectation pf a reduction in unrecognized tax benefits. Without limiting the foregoing, the words "may," "should," "could," "expect," "plan," "intend," "anticipate," "believe," "estimate," "predict," "designed," "potential," "continue," "target," "seek" and similar expressions are intended to identify forward-looking statements. All forward-looking statements included in this Report are based on information available to us up to, and including the date of this document, and we disclaim any obligation to update any such forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of various important factors, including but not limited to flaws in the assumptions and judgments upon which our forecasts and estimates are based; the development, severity, and duration of supply chain constraints, inflation, and the lingering effects of the COVID-19 pandemic; the failure of our cost reductions to affect our financial results as expected; our inability to make the investments that we plan to make or the failure of those investments to achieve the results we expect; our failure to execute on the transformation of the Vista business; loss of key personnel or our inability to recruit talented personnel to drive performance of our businesses; costs and disruptions caused by acquisitions and minority investments; the failure of businesses we acquire or invest in to perform as expected; our failure to develop and deploy our mass customization platform or the failure of the platform to drive the efficiencies and competitive advantages we expect; unanticipated changes in our markets, customers, or businesses; changes in the laws and regulations, or in the interpretation of laws and regulations, that affect our businesses; our failure to manage the growth and complexity of our business and expand our operations; our failure to maintain compliance with the covenants in our debt documents or to pay our debts when due; competitive pressures; general economic conditions, including the possibility of an economic downturn in some or all of our markets; and other factors described in this Report and the documents that we periodically file with the SEC.

Executive Overview

Cimpress is a strategically focused group of more than a dozen businesses that specialize in mass customization of printing and related products, via which we deliver large volumes of individually small-sized customized orders. Our products include a broad range of marketing materials, business cards, signage, promotional products, logo apparel, packaging, books and magazines, wall decor, photo merchandise, invitations and announcements, and other categories. Mass customization is a core element of the business model of each Cimpress business and is a competitive strategy which seeks to produce goods and services to meet individual customer needs with near mass production efficiency.

As of March 31, 2023, we have numerous operating segments under our management reporting structure that are reported in the following five reportable segments: Vista, PrintBrothers, The Print Group, National Pen, and All Other Businesses. Refer to Note 11 in our accompanying consolidated financial statements for additional information relating to our reportable segments and our segment financial measures.

We announced plans on March 23, 2023 to reduce costs within our Vista business and our central teams and implement organizational changes to support expanded profitability, reduced leverage and increased speed, focus, and accountability. These plans resulted in a restructuring charge of $30.1 million during the current quarter, with additional immaterial charges expected to be recognized during the fourth quarter of fiscal 2023. This restructuring action provided a small cost savings benefit during the current quarter due to the timing of the action, but we expect this action to deliver approximately $100 million of annualized pre-tax cost savings.

Financial Summary

The primary financial metric by which we set quarterly and annual budgets both for individual businesses and Cimpress wide is our adjusted free cash flow before cash interest expense; however, in evaluating the financial condition and operating performance of our business, management considers a number of metrics including revenue growth, organic constant-currency revenue growth, operating income, adjusted EBITDA, cash flow from operations and adjusted free cash flow. Reconciliations of our non-GAAP financial measures are included within the



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"Consolidated Results of Operations" and "Additional Non-GAAP Financial Measures" sections of Management's Discussion and Analysis. A summary of these key financial metrics for the three and nine months ended March 31, 2023 as compared to the three and nine months ended March 31, 2022 follows:

Third Quarter Fiscal Year 2023

•Revenue increased by 13% to $742.2 million.

•Constant-currency revenue increased 16% when excluding the revenue of acquired companies for the first twelve months after acquisition (a non-GAAP financial measure).

•Operating income increased by $16.2 million to a loss of $12.2 million.

•Adjusted EBITDA (a non-GAAP financial measure) increased by $35.5 million to $69.1 million.

•Diluted net loss per share attributable to Cimpress plc increased to a loss of $1.88 from a loss of $2.75 in the comparative period.

Year to Date Fiscal Year 2023

•Revenue increased by 6% to $2,290.8 million.

•Constant-currency revenue increased by 12% and 11% when excluding the revenue of acquired companies for the first twelve months after acquisition (both non-GAAP financial measures).

•Operating income decreased by $71.1 million to $3.4 million.

•Adjusted EBITDA (a non-GAAP financial measure) decreased by $17.4 million to $225.9 million.

•Diluted net loss per share attributable to Cimpress plc decreased to a loss of $8.19 from a loss of $0.91 in the comparative period.

•Cash provided by operating activities decreased by $63.2 million to $68.5 million.

•Adjusted free cash flow (a non-GAAP financial measure) decreased by $52.9 million to an outflow of $13.2 million.

For the three months ended March 31, 2023, reported revenue growth accelerated, mainly in our Vista business as product mix shifted back toward faster-growing small business products and we are comparing to a weaker period in the prior-year quarter that included the migration of Vista's U.S. website onto the new technology platform. Our Vista business experienced growth in new customer count and new customer bookings across all major markets. Promotional products, apparel, and gifts (PPAG) was our fastest-growing product category, with business cards, marketing materials, packaging and labels, and signage all showing strong year-over-year growth as well. Revenue growth in most Cimpress businesses continued to benefit from year-over-year increases in pricing, which has been one tool used to mitigate inflationary cost pressures. Currency exchange fluctuations had a negative effect during the current quarter.

For the three months ended March 31, 2023, the increase in operating income was primarily due to the incremental profit from the revenue growth described above. Gross profit growth benefited from higher volumes and the reduced net impact of cost inflation. We also realized cost efficiencies in advertising spend, and lower compensation and consulting-related operating expenses. These items were partially offset by an increase in restructuring charges primarily related to actions taken during the current quarter to reduce costs in the Vista business and in our central teams.

Adjusted EBITDA increased year over year for the three months ended March 31, 2023, primarily for the same reasons operating income increased. Adjusted EBITDA excludes restructuring charges, share-based compensation expense, certain impairments, and non-cash gains on the sale of assets, and includes the realized gains or losses on our currency derivatives intended to hedge adjusted EBITDA. The net year-over-year impact of currency on consolidated adjusted EBITDA was a benefit of approximately $1.6 million for the three months ended March 31, 2023.

Diluted net loss per share attributable to Cimpress plc increased for the three months ended March 31, 2023 primarily due to the improved operating loss described above, as well as significantly lower income tax expense year over year. These improvements were partially offset by increased interest expense and year-over-


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year impact from the net effect of unrealized currency losses caused by exchange rate volatility that more than offset realized gains recognized in the current quarter.

During the nine months ended March 31, 2023, cash from operations decreased $63.2 million year over year due primarily to less favorable working capital inflows of $22.0 million, largely driven by less favorable benefits from accounts payable due in part to timing, as well as negative working capital impacts from higher inventory levels that were intended to mitigate supply chain issues. Cash from operations was also negatively impacted year over year by higher cash interest costs and restructuring payments due to actions taken to reduce costs over the past year.

Adjusted free cash flow decreased year over year by $52.9 million for the nine months ended March 31, 2023, due to the operating cash flow decrease described above, partially offset by lower capitalized software and capitalized expenditures.

Consolidated Results of Operations

Consolidated Revenue

Our businesses generate revenue primarily from the sale and shipment of customized products. We also generate revenue, to a much lesser extent (and primarily in our Vista business), from digital services, graphic design services, website design and hosting, and email marketing services, as well as a small percentage of revenue from order referral fees and other third-party offerings. For additional discussion relating to segment revenue results, refer to the "Reportable Segment Results" section included below.

Total revenue and revenue growth by reportable segment for the three and nine months ended March 31, 2023 and 2022 are shown in the following table:

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