Roger Sherman moved from shoemaking, surveying, and commerce into law and public office in colonial Connecticut. Largely self-educated, he was admitted to the bar in 1754 and soon entered the legislature and judiciary. After moving to New Haven, he managed businesses, supported Yale College as its treasurer, and combined local responsibilities with service in the colony's assembly and Superior Court.

Sherman supported resistance to British measures through nonimportation and the committee of correspondence. In the Continental Congress, he worked on finance, military supply, and committees preparing the Declaration of Independence and Articles of Confederation. As one of the Declaration's Committee of Five, he helped review a text principally drafted by Thomas Jefferson. He favored taxes over excessive borrowing or paper currency.

At the Constitutional Convention of 1787, Sherman defended the political standing of the states while accepting the need for a more effective federal government. With Oliver Ellsworth, he helped advance the Connecticut Compromise: representation by population in the House and equal state representation in the Senate. This arrangement broke a central dispute between large and small states. It emerged from negotiation among many delegates, rather than from Sherman's efforts alone, and the resulting Constitution also accommodated slavery.

He helped secure ratification in Connecticut and then served in the United States House from 1789 to 1791 and Senate from 1791 until his death in 1793. A Federalist, he participated in establishing the machinery of the republic while retaining close ties to state and municipal government. He had also become New Haven's mayor in 1784. Sherman uniquely signed the Continental Association, Declaration, Articles, and Constitution. Those signatures reflect a career extending across successive systems of government, with his most consequential work centered on committees, institutional compromise, and legislation.