In June 1776, the Connecticut Assembly authorized Governor Jonathan Trumbull to "employ a suitable person to ride post from this Colony to Albany, and to any further or more northern place or stage as shall be necessary and his Honor shall direct, to carry and bring letters and intelligence, for the year ensuing." Governor Trumbull appointed Jesse Brown to this position. Brown served as an express rider from Connecticut to Albany, New York; Fort Ticonderoga; the Northern Army; General George Washington's Camp; and the Continental Congress at Philadelphia from at least June 1776 to May 1777. 

 At their meeting on March 11, 1777, Governor Trumbull and the Council of Safety "voted an order of twenty pounds on the Pay Table in favor of Jesse Brown, post to Gen. Washington and Congress, to be charged the Continent." On April 30, Brown returned from Congress in Philadelphia with an order to imprison former New Jersey Royal Governor William Franklin, the son of Benjamin Franklin. Brown also brought confirmation of the British raid on Danbury, Connecticut. In June, Brown reported to the Council that "he has been employed as a post rider, by means whereof he has not had opportunity to supply himself with cloathing or the necessary materials for manufacturing the same." He asked for permission to purchase a quantity of flax belonging to the state that was held by James Church of Hartford, and the Council permitted him to purchase one hundred weight of the flax.

 In October 1777, the Continental Congress observed that Brown "hath proved himself faithful and alert in that business" and employed him as an express rider in the Continental Service, which he continued to perform into 1780. In March 1779, a congressional committee observed that he had performed his duty "with much punctuality, fidelity and dispatch" and because he had supplied his own horses and forage allowed him more for his express services though his account "is the most exorbitant of the kind that was ever exhibited to the Commissioners."