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Related-Party Transactions
12 Months Ended
Dec. 31, 2019
Related Party Transactions [Abstract]  
Related-Party Transactions Related-Party Transactions

Our Chief Executive Officer is a member of the Board of Directors of Adobe Systems Incorporated (Adobe). During the years ended December 31, 2019, 2018, and 2017, we purchased $2.1 million, $3.3 million and $3.2 million, respectively, of services from Adobe. We had $0.2 million in revenues during the year ended December 31, 2019 and $0.1 million in revenues during the years ended December 31, 2018 and 2017 from Adobe. We had $0.2 million and an immaterial amount in payables as of December 31, 2019 and 2018, respectively, to Adobe. We had no outstanding receivables as of December 31, 2019 and 2018 from Adobe.    

One of our board members was a member of the Board of Directors of Cengage Learning, Inc. (Cengage) until December 23, 2019. During the years ended December 31, 2019, 2018, and 2017, we purchased $17.2 million, $15.1 million, and $11.5 million, respectively, of goods and services from Cengage.  We had $3.0 million, $2.5 million, and $1.9 million in revenues during the years ended December 31, 2019, 2018, and 2017, respectively, from Cengage. We had an immaterial amount and $0.1 million in payables as of December 31, 2019 and 2018, respectively, to Cengage. We had an immaterial amount of outstanding receivables as of December 31, 2019 and 2018, respectively, from Cengage.

One of our board members is also a member of the Board of Directors of Synack, Inc. (Synack). During the years ended December 31, 2019, 2018, and 2017, we purchased $0.4 million, $0.1 million, and $0.1 million, respectively, of services from Synack.

The immediate family of one of our board members is a member of the Board of Directors of PayPal Holdings, Inc. (PayPal). During the years ended December 31, 2019, 2018, and 2017, we incurred payment processing fees of $1.6 million, $1.3 million, and $1.0 million, respectively, to PayPal.

One of our board members is the Chief Executive Officer of the San Francisco 49ers (49ers). During the year ended December 31, 2019, we purchased $0.2 million of advertisements from the 49ers.