Prior to his election to the state senate, he worked in the field of business finance, trading bonds in New York City.

Since his arrival to the Senate, Pipkin has authored legislation that include creating a task force to bring broadband internet to his eastern shore constituents; creating a committee that will ensure responsible handling of taxpayer dollars by the state government; and advocating for an elected school board in Cecil County to increase public involvement in public schools.

On August 5, 2013, Pipkin announced that he would retire from the State Senate, effective the following week, to pursue a graduate degree in sports management at Southern Methodist University in Dallas, Texas.

[5][6] As a resident of Stevensville, Pipkin himself has been affected by traffic congestion on the Chesapeake Bay Bridge, and has fought to reduce the problem.

The bills would have, among other things, made various modifications to the governing board of the Maryland Transportation Authority (MdTA),[7] banned trucks from the bridge when one of its dual spans is carrying two-way traffic,[8] and waived tolls whenever backups extended beyond a certain point.

In the 2006 Maryland General Assembly session, Pipkin once again tried to pass parts of the Bay Bridge Users' Bill of Rights, this time more successfully.