[2][3] It was a small printing shop founded with $500 in capital and originally named Reynolds and Gardner.

[3] A controlling interest in the company was acquired in 1939 by Richard Hallam Grant, Sr., ending the Reynolds family ownership.

[3] In the 1960s, Reynolds opened new printing facilities in North Hollywood, Los Angeles,[4] New Jersey and Canada.

[6] In 1986, the company acquired Arnold Corporation, which increased Reynolds' revenues 50 percent and expanded its market presence to other industries besides car dealerships.

[5] He led the company's first large-scale lay-off in the printing division,[3] cutting headcount and manufacturing space in half.

[5] After Holmes retired, he was replaced by former IBM executive Lloyd G. "Buzz" Waterhouse, who created an eBusiness department to focus on internet technologies.

[3] In 2000, Reynolds also acquired the HAC Group, a learning, customer relationship management and web services company for retailers and manufacturers.

[3][8][9][a] In November 2002, it acquired Networkcar Inc. (now Verizon Networkfleet) and further developed its telematics device, CAReader.

Reynolds Healthcare Systems later acquired a business document company, Fiscal Information, which serves radiologists.

[19][20][21] In 2008, Reynolds acquired DiversiForm, a Beaverton, Oregon-based printer of forms and business documents for car dealerships.

[25] In 2017, Reynolds acquired Xpressdocs, a Fort Worth, Texas-based company specializing in the marketing needs of franchise organizations.

[26] On February 14, 2020, Reynolds announced that they were acquiring GoMoto, a developer of a self-service kiosk technology for checking in at dealerships in North America.

Brockman is accused of using "a family charitable trust based in Bermuda and other offshore entities to hide assets from the Internal Revenue Service while failing to pay taxes", totaling $2 billion in untaxed income.

[28] On December 17, 2020, Reynolds announced that they were acquiring ReconTRAC®, a developer of a web-based software that is meant to assist dealerships with the process of reconditioning used cars.

[29] On June 8, 2021, Reynolds announced that they were acquiring Gubagoo, a leading provider of conversational commerce and digital retail tools for both automotive dealerships and OEMs in North America.

[3][18] For example, one Reynolds application called AddOnAuto can visualize what a car will look like with accessories,[38][39] while docuPAD adds a touch-screen on top of a desk that customers use to go through vehicle sales paperwork and interact with options.

By the 1940s, Reynolds' business was divided into four main areas: automotive, medical, custom forms and Post-Rite Peg Boards.

This eliminated the need for clients to ship data to Reynolds in tapes and allowed daily access to online services.

[43][44][45] By 1986, the VIM-based dealer management computer systems had helped Reynolds acquire a 45 percent market-share and was on its fifth generation with 9,000 installations.

ERA allows users to manage logistics for sales, finance, service and parts across departments.

[46] In February 2000, Reynolds formed a joint venture with Automatic Data Processing, Inc. and CCC Information Services, Inc. to create a web-based dealer-to-dealer parts network called ChoiceParts.

"[3][47] According to Automotive News, the Unix-based system could support more users, but the Microsoft software was compatible with more of the newer applications being used by dealerships.