In 1985 Earl joined Smith, Burke and Azzam Advertising in Baltimore where future Gaga partner Richard Smith was Senior VP and Creative Director. He worked in account management roles on Trump Plaza Hotel and Casino, Playboy Magazine (consumer and trade) and the Baltimore Orioles. He continued developing his agency experience at Van Sant Dugdale in Baltimore in senior account management positions on retail Banking accounts and on SallieMae. Earl then took operating roles in various early stage companies including Cellular One in the DC area where he managed the entire dealer network of over 50 dealers through the acquisition by Southwestern Bell Mobile Systems, in the early days of the mobile telephone industry in 1991. He then became Director of Marketing of American Mobile Satellite Corporation (AMSC), the sole FCC licensee to provide mobile telephone voice, data and fax services to North America via geostationary satellite. AMSC was the first company to develop a dual mode-satellite/cellular mobile phone that it marketed through its national channel of cellular phone dealers. After 5 years overseeing marketing through the development, launch and rollout of national service, Earl was tapped to be President of the DIGEX, Incorporated Web Site Management Services Division. He led Digex Web Site Management, now part of Verizon Communications, to become the world’s largest provider of dedicated Web Site Management Services for Fortune 2000 corporations. Earl participated in a successful IPO of DIGEX, Inc. in 1997, raising $48 million, then in the sale of the company for $178 million in June,1998. From there he became a Series A investor and EVP at Akamai Technologies, Inc. (NASDQ:AKAM) in Cambridge, Massachusetts, from its inception through its IPO and highest growth years. In just two years, Earl built a global sales, marketing, service and support organization of 650 employees in 6 countries and he grew revenue from $0 to $165 million annually.
Following Akamai, Earl dedicated his full time effort as board chair of KIPPDC, a Washington DC charter school. From 2003 through 2008, he guided management through an aggressive expansion of KIPPDC from 1 middle school serving 160 students in the most underserved areas of DC, to a 7-school system, including three elementary schools, three middle schools and 1 high school, all in DC. Today, KIPPDC is the number 1 performing charter or public school/school system in the DC serving over 5,200 students at 16 schools on 6 campuses in the city.
In 2008 Earl co-founded Basho Technologies, Inc., a distributed database open source software company in Cambridge, MA and led the company as Chairman and CEO though June 2011. He relinquished the CEO role and remained Chairman of the Board through January 2014. Basho is a key player in the global distributed database software market and it now has several hundred Fortune 2000 company clients, Including State Farm Insurance, Best Buy, Comcast, Yahoo Japan, Symantec, Yammer and McAffe.