A native of Clovis, California, the 6 ft 2 in (1.88 m), 195 lb (88 kg) Shepard attended Stanford University, graduating in 1953 after serving as the captain of the first Cardinal team (then nicknamed the Indians) to play in the College World Series.

[1] He signed with the Pittsburgh Pirates upon graduation on June 16 and made his Major League debut three days later against the St. Louis Cardinals at Sportsman's Park, substituting for starting catcher Mike Sandlock and singling in two at bats against Vinegar Bend Mizell.

Despite their struggles, and his first-game jitters in 1953, Shepard gained a reputation as a stalwart defensive player, batted .304 in his first full season (when he was named Pirates' rookie of the year and selected to The Sporting News' all-rookie team[1]) and became one of the team leaders.

[1] After serving as Pittsburgh's regular catcher in 1956, appearing in a career-high 100 games, he announced his retirement to become development director at his alma mater and begin a full-time career in business.

He served as president and chief executive of a San Francisco-area telecommunications firm and a baseball equipment and indoor baseball and entertainment center company, and was a management consultant as well as a philanthropist on behalf of multiple Palo Alto, California-area institutions.