zs-20220224
FALSE000171368300017136832022-02-242022-02-24


UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
___________________________________
FORM 8-K
___________________________________
CURRENT REPORT
Pursuant to Section 13 or 15(d)
of the Securities Exchange Act of 1934
 
Date of Report (date of earliest event reported)
February 24, 2022
___________________________________
Zscaler, Inc.
(Exact name of registrant as specified in its charter)
___________________________________
Delaware
(State or other jurisdiction of incorporation or organization)
001-38413
(Commission File Number)
26-1173892
(I.R.S. Employer Identification Number)
120 Holger Way
San Jose, California 95134
(Address of principal executive offices and zip code)
(408) 553-0288
(Registrant's telephone number, including area code)
Not Applicable
(Former name or former address, if changed since last report)
___________________________________
Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:
Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))
Securities registered pursuant to Section 12(b) of the Act:
Title of each classTrading Symbol(s)Name of each exchange of which registered
Common Stock, $0.001 Par ValueZSThe Nasdaq Stock Market LLC

 Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).
 
Emerging growth company
 
If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.  



Item 2.02 Results of Operations and Financial Condition.
On February 24, 2022, Zscaler, Inc. issued a press release announcing its financial results for the second fiscal quarter ended January 31, 2022. A copy of the press release is furnished herewith as Exhibit 99.1 and incorporated herein by reference.
The information contained in this Item 2.02 and Item 9.01 in this Current Report on Form 8-K, including the accompanying Exhibit 99.1 hereto, shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, regardless of any general incorporation language in such filings, unless expressly incorporated by specific reference in such filing.    
Item 9.01 Financial Statements and Exhibits.
(d) Exhibits.
Exhibit No.Description of Exhibit
99.1
 
 



SIGNATURES
Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.
Zscaler, Inc.
February 24, 2022/s/Remo Canessa
Remo Canessa
Chief Financial Officer


Document


Exhibit 99.1

Zscaler Reports Second Quarter Fiscal 2022 Financial Results
Second Quarter Highlights
Revenue grows 63% year-over-year to $255.6 million
Calculated billings grows 59% year-over-year to $367.7 million
Deferred revenue grows 70% year-over-year to $759.9 million
GAAP net loss of $100.4 million compared to GAAP net loss of $67.5 million on a year-over-year basis
Non-GAAP net income of $19.2 million compared to non-GAAP net income of $14.0 million on a year-over-year basis
SAN JOSE, California - February 24, 2022 - Zscaler, Inc. (Nasdaq: ZS), the leader in cloud security, today announced financial results for its second quarter of fiscal year 2022, ended January 31, 2022.
"Driven by continued demand for our Zero Trust security platform, we delivered strong results for the second quarter, with our year-over-year revenue growth rate reaching its highest level in three years, even as we surpassed $1 billion in annualized revenue,” said Jay Chaudhry, Chairman and CEO of Zscaler. "The importance of our Zero Trust Exchange architecture has never been clearer to customers undertaking digital transformation. Customers are not only gaining security advantages from our Zero Trust model but they are also reaping the benefits of faster innovation and economics from our global cloud, which is now processing more than 210 billion transactions per day.”

Second Quarter Fiscal 2022 Financial Highlights
Revenue: $255.6 million, an increase of 63% year-over-year.
Income (loss) from operations: GAAP loss from operations was $83.9 million, or 33% of total revenue, compared to $53.9 million, or 34% of total revenue, in the second quarter of fiscal 2021. Non-GAAP income from operations was $22.3 million, or 9% of total revenue, compared to $14.8 million, or 9% of total revenue, in the second quarter of fiscal 2021.
Net income (loss): GAAP net loss was $100.4 million, compared to $67.5 million in the second quarter of fiscal 2021. Non-GAAP net income was $19.2 million, compared to $14.0 million in the second quarter of fiscal 2021.
Net income (loss) per share: GAAP net loss per share was $0.71, compared to $0.50 in the second quarter of fiscal 2021. Non-GAAP net income per share was $0.13, compared to $0.10 in the second quarter of fiscal 2021.
Cash flow: Cash provided by operations was $48.3 million, or 19% of revenue, compared to $30.4 million, or 19% of revenue, in the second quarter of fiscal 2021. Free cash flow was $29.4 million, or 12% of revenue, compared to $18.0 million, or 11% of revenue, in the second quarter of fiscal 2021.
Deferred revenue: $759.9 million as of January 31, 2022, an increase of 70% year-over-year.
Cash, cash equivalents and short-term investments: $1,621.2 million as of January 31, 2022, an increase of $118.7 million from July 31, 2021.

Recent Business Highlights

Launched the general availability of new Workload Communications solution, part of the Zscaler Zero Trust Exchange™, which extends Zero Trust security to workloads and applications hosted in public clouds. Zscaler’s cloud-native platform helps IT teams simplify multi-cloud workload connectivity by moving away from traditional IP-based routing and VPNs between cloud environments to expedite enterprises' cloud transformation initiatives.

Recognized as a Leader in the inaugural Gartner 2022 Magic Quadrant for Security Service Edge (SSE). Zscaler is positioned as the vendor with the highest ‘Ability to Execute’ among the 11 vendors that were recognized for this
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report. Gartner assesses vendors’ ability to execute based on a combination of critical factors including products/services, customer experience, market responsiveness, track record, marketing execution, sales execution/pricing, operations, and overall viability.

Achieved 100% renewable energy through a combination of directly purchased renewable energy and renewable energy credits (RECs) for its offices and 150+ data centers that run the Zscaler Zero Trust Exchange. Zscaler’s cloud-based architecture enables customers to improve their security posture and user experience while reducing the need to purchase, maintain, and power on-premises security hardware, thus enabling customers to reduce their IT equipment overhead and consequently their energy usage.

Financial Outlook
For the third quarter of fiscal 2022, we expect:
Total revenue of $270 million to $272 million
Non-GAAP income from operations of $19 million to $20 million 
Non-GAAP net income per share of approximately $0.10 to $0.11, assuming approximately 149 million to 150 million common shares outstanding
For the full year fiscal 2022, we expect:
Total revenue of $1.045 billion to $1.05 billion
Calculated billings of $1.365 billion to $1.37 billion
Non-GAAP income from operations of $95 million to $98 million
Non-GAAP net income per share of $0.54 to $0.56, assuming approximately 149 million to 150 million common shares outstanding
These statements are forward-looking and actual results may differ materially. Refer to the Forward-Looking Statements safe harbor below for information on the factors that could cause our actual results to differ materially from these forward-looking statements.
Guidance for non-GAAP income from operations excludes stock-based compensation expense and related employer payroll taxes, amortization expense of acquired intangible assets, asset impairment related to facility exit, amortization of debt discount and issuance costs and income tax effects generated by intangible assets acquired in business acquisitions. Guidance for non-GAAP net income per share includes the anti-dilutive impact of the capped call transactions entered into in connection with our convertible senior notes. We have not reconciled our expectations to non-GAAP income from operations and non-GAAP net income per share to their most directly comparable GAAP measures because certain items are out of our control or cannot be reasonably predicted. Accordingly, a reconciliation for the guidance for non-GAAP income from operations and non-GAAP net income per share is not available without unreasonable effort.
Conference Call and Webcast Information
Zscaler will host a conference call for analysts and investors to discuss its second quarter fiscal 2022 earnings results and outlook for its third quarter of fiscal 2022 and full year fiscal 2022 today at 1:30 p.m. Pacific time (4:30 p.m. Eastern time).
Date:Thursday, February 24, 2022
Time:1:30 p.m. PT
Webcast:
https://ir.zscaler.com
Dial-in number:918-922-3018
Upcoming Conferences
Third quarter of fiscal 2022 virtual investor conference participation schedule:

Berenberg Thematic Software Conference 2022
Wednesday, March 2, 2022
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JMP Securities Technology Conference
Monday, March 7, 2022

Wolfe Research Virtual "March Madness" Software Conference
Wednesday, March 23, 2022

Sessions which offer a webcast will be available on the Investor Relations section of the Zscaler website at https://ir.zscaler.com.

Forward-Looking Statements
This press release contains forward-looking statements that involve risks and uncertainties, including, but not limited to, statements regarding our future financial and operating performance, including our financial outlook for the third quarter of fiscal 2022 and full year fiscal 2022. There are a significant number of factors that could cause actual results to differ materially from statements made in this press release, including but not limited to: the duration and global impact of COVID-19 on our business, operations and financial results and the economy in general; our limited operating history; our ability to identify and effectively implement the necessary changes to address execution challenges; risks associated with managing our rapid growth, including fluctuations from period to period; our limited experience with new product and subscription and support introductions and the risks associated with new products and subscription and support offerings, including the discovery of software bugs; our ability to attract and retain new customers; the failure to timely develop and achieve market acceptance of new products and subscriptions as well as existing products and subscription and support; rapidly evolving technological developments in the market for network security products and subscription and support offerings and our ability to remain competitive; length of sales cycles; and general market, political, economic and business conditions.
Additional risks and uncertainties that could affect our financial results are included under the captions “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” set forth from time to time in our filings and reports with the Security Exchange Commission (SEC), including our Annual Report on Form 10-K for the fiscal year ended July 31, 2021 filed on September 16, 2021, as well as future filings and reports by us, copies of which are available on our website at ir.zscaler.com and on the SEC’s website at www.sec.gov. You should not rely on these forward-looking statements, as actual outcomes and results may differ materially from those contemplated by these forward-looking statements as a result of such risks and uncertainties. Additional information will also be set forth in other filings that we make with the SEC from time to time. All forward-looking statements in this press release are based on information available to us as of the date hereof, and we do not assume any obligation to update the forward-looking statements provided to reflect events that occur or circumstances that exist after the date on which they were made.

Use of Non-GAAP Financial Information
We believe that the presentation of non-GAAP financial information provides important supplemental information to management and investors regarding financial and business trends relating to our financial condition and results of operations. For further information regarding why we believe that these non-GAAP measures provide useful information to investors, the specific manner in which management uses these measures, and some of the limitations associated with the use of these measures, please refer to the “Explanation of Non-GAAP Financial Measures" section of this press release.

About Zscaler
Zscaler (Nasdaq: ZS) accelerates digital transformation so customers can be more agile, efficient, resilient, and secure. The Zscaler Zero Trust Exchange protects thousands of customers from cyberattacks and data loss by securely connecting users, devices, and applications in any location. Distributed across more than 150 data centers globally, the SASE-based Zero Trust Exchange is the world’s largest in-line cloud security platform.
Zscaler™ and the other trademarks listed at https://www.zscaler.com/legal/trademarks are either (i) registered trademarks or service marks or (ii) trademarks or service marks of Zscaler, Inc. in the United States and/or other countries. Any other trademarks are the properties of their respective owners.
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Investor Relations Contacts

Bill Choi, CFA
SVP, Investor Relations and Strategic Finance
(408) 816-1478
ir@zscaler.com

Natalia Wodecki
Media Relations Contact
press@zscaler.com

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ZSCALER, INC.
Condensed Consolidated Statements of Operations
(in thousands, except per share amounts)
(unaudited)
Three Months EndedSix Months Ended
January 31,January 31,
2022202120222021
Revenue$255,563 $157,044 $486,080 $299,622 
Cost of revenue (1) (2)
57,783 34,135 109,952 65,862 
Gross profit197,780 122,909 376,128 233,760 
Operating expenses:
Sales and marketing (1) (2)
175,073 110,403 328,859 207,292 
Research and development (1) (2)
69,195 41,751 134,411 77,521 
General and administrative (1) (3)
37,444 24,653 71,161 45,512 
Total operating expenses281,712 176,807 534,431 330,325 
Loss from operations(83,932)(53,898)(158,303)(96,565)
Interest income557 755 1,030 1,695 
Interest expense (4)
(14,040)(13,245)(27,875)(26,294)
Other income (expense), net(844)518 (1,433)786 
Loss before income taxes(98,259)(65,870)(186,581)(120,378)
Provision for income taxes2,161 1,671 4,640 2,169 
Net loss$(100,420)$(67,541)$(191,221)$(122,547)
Net loss per share, basic and diluted
$(0.71)$(0.50)$(1.37)$(0.91)
Weighted-average shares used in computing net loss per share, basic and diluted
140,515 135,024 139,901 134,238 
(1) Includes stock-based compensation expense and related payroll taxes as follows:
Cost of revenue$5,766 $3,308 $11,085 $6,574 
Sales and marketing47,666 33,864 91,130 66,518 
Research and development30,000 17,747 58,570 32,647 
General and administrative20,613 12,194 39,354 21,703 
Total$104,045 $67,113 $200,139 $127,442 
(2) Includes amortization expense of acquired intangible assets as follows:
Cost of revenue$2,000 $1,503 $4,056 $3,007 
Sales and marketing
178 73 348 146 
Research and development53 — 53 — 
Total$2,231 $1,576 $4,457 $3,153 
(3) Includes asset impairment related to facility exit as follows:
$— $— $— $416 
(4) Includes amortization of debt discount and issuance costs as follows:
$13,680 $12,882 $27,156 $25,572 

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ZSCALER, INC.
Condensed Consolidated Balance Sheets
(in thousands)
(unaudited)
January 31,July 31,
20222021
Assets
Current assets:
Cash and cash equivalents$409,819 $275,898 
Short-term investments1,211,390 1,226,654 
Accounts receivable, net269,449 257,109 
Deferred contract acquisition costs69,025 57,373 
Prepaid expenses and other current assets29,482 31,269 
Total current assets1,989,165 1,848,303 
Property and equipment, net121,195 108,576 
Operating lease right-of-use assets42,837 44,339 
Deferred contract acquisition costs, noncurrent165,480 149,657 
Acquired intangible assets, net29,272 32,129 
Goodwill59,823 58,977 
Other noncurrent assets14,249 15,650 
Total assets$2,422,021 $2,257,631 
Liabilities and Stockholders’ Equity
Current liabilities:
Accounts payable$13,499 $12,547 
Accrued expenses and other current liabilities31,096 22,908 
Accrued compensation83,863 93,622 
Deferred revenue687,919 571,286 
Operating lease liabilities19,665 19,842 
Total current liabilities836,042 720,205 
Convertible senior notes, net940,692 913,538 
Deferred revenue, noncurrent72,012 59,315 
Operating lease liabilities, noncurrent29,280 31,225 
Other noncurrent liabilities4,628 4,453 
Total liabilities1,882,654 1,728,736 
Stockholders’ Equity
Common stock141 139 
Additional paid-in capital1,341,346 1,131,006 
Accumulated other comprehensive loss(9,299)(650)
Accumulated deficit(792,821)(601,600)
Total stockholders’ equity539,367 528,895 
Total liabilities and stockholders’ equity$2,422,021 $2,257,631 

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ZSCALER, INC.
Condensed Consolidated Statements of Cash Flows
(in thousands)
(unaudited)
Six Months Ended
January 31,
20222021
Cash Flows From Operating Activities
Net loss$(191,221)$(122,547)
Adjustments to reconcile net loss to cash provided by operating activities:
Depreciation and amortization expense19,005 13,327 
Amortization expense of acquired intangible assets4,457 3,153 
Amortization of deferred contract acquisition costs31,038 18,123 
Amortization of debt discount and issuance costs27,156 25,572 
Non-cash operating lease costs12,411 9,500 
Stock-based compensation expense188,891 118,565 
Amortization of investment premiums, net of accretion of purchase discounts4,662 5,446 
Deferred income taxes(659)(981)
Impairment of assets— 416 
Other295 59 
Changes in operating assets and liabilities, net of effects of business acquisitions
Accounts receivable(12,622)(24,681)
Deferred contract acquisition costs(58,513)(43,154)
Prepaid expenses, other current and noncurrent assets4,903 6,722 
Accounts payable(103)4,627 
Accrued expenses, other current and noncurrent liabilities5,029 1,733 
Accrued compensation(9,759)(1,583)
Deferred revenue129,594 78,884 
Operating lease liabilities(13,031)(9,245)
Net cash provided by operating activities141,533 83,936 
Cash Flows From Investing Activities
Purchases of property, equipment and other assets(20,442)(19,403)
Capitalized internal-use software(8,275)(4,272)
Payments for business acquisitions, net of cash acquired(380)— 
Purchases of short-term investments(624,254)(419,638)
Proceeds from maturities of short-term investments629,411 283,815 
Proceeds from sale of short-term investments— 11,500 
Net cash used in investing activities(23,940)(147,998)
Cash Flows From Financing Activities
Proceeds from issuance of common stock upon exercise of stock options4,871 11,245 
Proceeds from issuance of common stock under the employee stock purchase plan11,509 8,563 
Payment of deferred consideration related to a business acquisition(50)(2,250)
Other(2)— 
Net cash provided by financing activities16,328 17,558 
Net increase (decrease) in cash and cash equivalents (1)
133,921 (46,504)
Cash and cash equivalents at beginning of period (1)
275,898 141,851 
Cash and cash equivalents at end of period (1)
$409,819 $95,347 
_________
(1) We did not hold restricted cash for any periods presented.

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ZSCALER, INC.
Reconciliation of GAAP to Non-GAAP Financial Measures
(in thousands, except percentages)
(unaudited)
Three Months EndedSix Months Ended
January 31,January 31,
2022202120222021
Revenue$255,563 $157,044 $486,080 $299,622 
Non-GAAP Gross Profit and Non-GAAP Gross Margin
GAAP gross profit$197,780 $122,909 $376,128 $233,760 
Add:
Stock-based compensation expense and related payroll taxes5,766 3,308 11,085 6,574 
Amortization expense of acquired intangible assets2,000 1,503 4,056 3,007 
Non-GAAP gross profit$205,546 $127,720 $391,269 $243,341 
GAAP gross margin77 %78 %77 %78 %
Non-GAAP gross margin80 %81 %80 %81 %
Non-GAAP Income from Operations and Non-GAAP Operating Margin
GAAP loss from operations$(83,932)$(53,898)$(158,303)$(96,565)
Add:
Stock-based compensation expense and related payroll taxes104,045 67,113 200,139 127,442 
Amortization expense of acquired intangible assets2,231 1,576 4,457 3,153 
Asset impairment related to facility exit (1)
— — — 416 
Non-GAAP income from operations$22,344 $14,791 $46,293 $34,446 
GAAP operating margin(33)%(34)%(33)%(32)%
Non-GAAP operating margin%%10 %11 %
___________
(1) Consists of asset impairment charges related to the relocation of our corporate headquarters.
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ZSCALER, INC.
Reconciliation of GAAP to Non-GAAP Financial Measures
(in thousands, except per share amounts)
(unaudited)
Three Months EndedSix Months Ended
January 31,January 31,
2022202120222021
Non-GAAP Net Income per Share, Diluted
GAAP net loss$(100,420)$(67,541)$(191,221)$(122,547)
Stock-based compensation expense and related payroll taxes104,045 67,113 200,139 127,442 
Amortization expense of acquired intangible assets 2,231 1,576 4,457 3,153 
Asset impairment related to facility exit (1)
— — — 416 
Amortization of debt discount and issuance costs13,680 12,882 27,156 25,572 
Provision for income taxes (2)
(361)— (361)— 
Non-GAAP net income$19,175 $14,030 $40,170 $34,036 
GAAP net loss per share, diluted$(0.71)$(0.50)$(1.37)$(0.91)
Stock-based compensation expense and related payroll taxes0.70 0.46 1.35 0.88 
Amortization expense of acquired intangible assets0.01 0.01 0.03 0.02 
Asset impairment related to facility exit (1)
— — — — 
Amortization of debt discount and issuance costs0.09 0.09 0.18 0.18 
Provision for income taxes (2)
— — — — 
Adjustment to total fully diluted earnings per share (3)
0.04 0.04 0.08 0.07 
Non-GAAP net income per share, diluted$0.13 $0.10 $0.27 $0.24 
Denominator:
Weighted-average shares used in computing GAAP net loss per share, diluted140,515 135,024 139,901 134,238 
Potentially diluted shares10,687 10,719 10,898 10,180 
Antidilutive impact of capped call transactions (4)
(2,401)(1,120)(2,542)(317)
Weighted-average shares used in computing non-GAAP net income per share, diluted148,801 144,623 148,257 144,101 
___________
(1) Consists of asset impairment charges related to the relocation of our corporate headquarters.

(2) We use our GAAP provision for income taxes for purposes of determining our non-GAAP income tax expense. The difference between our GAAP and non-GAAP income tax expense represents the effects of stock-based compensation expense recognized in foreign jurisdictions and any income tax benefits associated with business combinations. The income tax benefit related to stock-based compensation expense included in the GAAP provision for income taxes was not material for all periods presented. In the fiscal quarter ended January 31, 2022, we recorded a tax benefit of $0.4 million generated by intangible assets acquired in a business acquisition.

(3) The sum of the fully diluted earnings per share impact of individual reconciling items may not total to fully diluted Non-GAAP net income per share due to the weighted-average shares used in computing the GAAP net loss per share differs from the weighted-average shares used in computing the Non-GAAP net income per share and due to rounding of the individual reconciling items. The GAAP net loss per share calculation uses a lower share count as it excludes potentially dilutive shares, which are included in calculating the non-GAAP net income per share.

(4) We exclude the in-the-money portion of our convertible senior notes for non-GAAP weighted-average diluted shares as they are covered by our capped call transactions. Our outstanding capped call transactions are antidilutive under GAAP, but are expected to mitigate the dilutive effect of our convertible notes and therefore are included in the calculations of non-GAAP diluted shares outstanding.
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ZSCALER, INC.
Reconciliation of GAAP to Non-GAAP Financial Measures
(in thousands, except percentages)
(unaudited)
Three Months EndedSix Months Ended
January 31,January 31,
2022202120222021
Calculated Billings
Revenue$255,563 $157,044 $486,080 $299,622 
Add: Total deferred revenue, end of period759,931 446,817 759,931 446,817 
Less: Total deferred revenue, beginning of period(647,816)(371,900)(630,601)(369,767)
Calculated billings$367,678 $231,961 $615,410 $376,672 
Free Cash Flow
Net cash provided by operating activities$48,262 $30,404 $141,533 $83,936 
Less: Purchases of property, equipment and other assets
(13,988)(10,499)(20,442)(19,403)
Less: Capitalized internal-use software
(4,825)(1,871)(8,275)(4,272)
Free cash flow$29,449 $18,034 $112,816 $60,261 
As a percentage of revenue:
Net cash provided by operating activities19 %19 %29 %28 %
Less: Purchases of property, equipment and other assets
(5)%(7)%(4)%(7)%
Less: Capitalized internal-use software
(2)%(1)%(2)%(1)%
Free cash flow margin12 %11 %23 %20 %


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ZSCALER, INC.
Explanation of Non-GAAP Financial Measures
In addition to our results determined in accordance with generally accepted accounting principles in the United States of America (GAAP), we believe the following non-GAAP measures are useful in evaluating our operating performance. We use the following non-GAAP financial information to evaluate our ongoing operations and for internal planning and forecasting purposes. We believe that non-GAAP financial information, when taken collectively, may be helpful to investors because it provides consistency and comparability with past financial performance. However, non-GAAP financial information is presented for supplemental informational purposes only, has limitations as an analytical tool and should not be considered in isolation or as a substitute for financial information presented in accordance with GAAP. In particular, free cash flow is not a substitute for cash provided by operating activities. Additionally, the utility of free cash flow as a measure of our liquidity is further limited as it does not represent the total increase or decrease in our cash balance for a given period. In addition, other companies, including companies in our industry, may calculate similarly-titled non-GAAP measures differently or may use other measures to evaluate their performance, all of which could reduce the usefulness of our non-GAAP financial measures as tools for comparison. A reconciliation of our historical non-GAAP financial measures to their most directly comparable financial measures stated in accordance with GAAP has been included in this press release. Investors are cautioned that there are a number of limitations associated with the use of non-GAAP financial measures and key metrics as analytical tools. Investors are encouraged to review these reconciliations, and not to rely on any single financial measure to evaluate our business.
Expenses Excluded from Non-GAAP Measures
Stock-based compensation expense is excluded primarily because it is a non-cash expense that management believes is not reflective of our ongoing operational performance. Employer payroll taxes related to stock-based compensation, which is a cash expense, are excluded because these are tied to the timing and size of the exercise or vesting of the underlying equity awards and the price of our common stock at the time of vesting or exercise, which may vary from period to period independent of the operating performance of our business. Amortization expense of intangible assets acquired in business acquisitions and related income tax effects, if applicable, are excluded because these are considered by management to be outside of our core business operating performance. Asset impairments related to facility exit costs are excluded because such charges are not reflective of our ongoing operational performance. Amortization of debt discount and issuance costs from our convertible senior notes are excluded because these are non-cash expenses and are not reflective of our ongoing operational performance. We estimate the tax effect of these items on our non-GAAP results and may adjust our GAAP provision for income taxes, if such effects have a material impact to our non-GAAP results.
Non-GAAP Financial Measures
Non-GAAP Gross Profit and Non-GAAP Gross Margin. We define non-GAAP gross profit as GAAP gross profit excluding stock-based compensation expense and related employer payroll taxes and amortization expense of acquired intangible assets. We define non-GAAP gross margin as non-GAAP gross profit as a percentage of revenue.
Non-GAAP Income from Operations and Non-GAAP Operating Margin. We define non-GAAP income from operations as GAAP loss from operations excluding stock-based compensation expense and related employer payroll taxes, amortization expense of acquired intangible assets, asset impairment related to facility exit and certain litigation-related expenses. We define non-GAAP operating margin as non-GAAP income from operations as a percentage of revenue.
Non-GAAP Net Income per Share, Diluted. We define non-GAAP net income as GAAP net loss excluding stock-based compensation expense and related employer payroll taxes, amortization expense of acquired intangible assets, asset impairment related to facility exit, amortization of debt discount and issuance costs, income tax effects generated by the effects of stock-based compensation expense recognized in foreign jurisdictions and any income tax benefits associated with business combinations. We define non-GAAP net income per share, diluted, as non-GAAP net income divided by the weighted-average diluted shares outstanding, which includes the dilutive effect of potentially diluted common stock equivalents outstanding during the period and the antidilutive impact of the capped call transactions entered into in connection with our convertible senior notes.
Calculated Billings. We define calculated billings as total revenue plus the change in deferred revenue in a period. Calculated billings in any particular period aims to reflect amounts invoiced for subscriptions to access our cloud platform, together with related support services for our new and existing customers. We typically invoice our customers annually in advance, and to a lesser extent quarterly in advance, monthly in advance or multi-year in advance.
Free Cash Flow and Free Cash Flow Margin. We define free cash flow as net cash provided by operating activities less purchases of property, equipment and other assets and capitalized internal-use software. We define free cash flow margin as free cash flow divided by revenue. We believe that free cash flow and free cash flow margin are meaningful indicators of liquidity information to management and investors about the amount of cash generated from our operations that, after the investments in property, equipment and other assets and capitalized internal-use software, can be used for strategic initiatives.
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