From 1993 to 1995, Clifford served on the San Francisco Commission for National Service. In 1995, he assisted Supervisor Carole Migden in formulating the SF wage Subsidy program and hired three former general assistance recipients during the process. In 1996, Clifford supported as a ballot signer the state minimum wage increase, Proposition 210. In 1997, Clifford was a small business spokesperson against the repeal of daily overtime and also became one of the first small businesses to offer domestic partner benefits. Clifford was honored in 1999 with a Goodwill Graduate Employer Showcase Award. In 2002, he received the San Francisco Council of District Merchants Community Service Award.
In 1997, Clifford was elected to the Mill Valley City Council where he championed efforts for watershed protection, noise reduction and cleaner air. In 2005, his last year on the City Council, Mill Valley was selected by Money Magazine as the best place to live in California.
In 1999, Clifford was appointed by Governor Davis and reappointed in 2003 by Governor Schwarzennegger to serve on the San Francisco Bay Regional Water Quality Control Board. He was selected by the Board to serve on the Bay Conservation and Development Commission (BCDC). As a BCDC appointee, Clifford served seven years on the Regional Airport Planning Committee and was its Chairperson for his last two years.
Clifford, a dedicated small business advocate, served on the Board of Directors of the San Francisco Chamber of Commerce (2003-2006) and chaired their Small Business Advisory Council for two years. From 2002 to 2005, Clifford was the President of the San Francisco Small Business Network, an umbrella group of 18 business organizations representing over 15,000 employees.