Caleb Shepherd began coxing at Hamilton Boys’ High School and Waikato Rowing Club in 2006.
He made his first New Zealand team in the junior coxed four in 2010 where the crew placed 6th at the World Rowing Junior Championships. Caleb was selected in the same boat class in 2011 and won silver at the World Rowing Championships at the London Olympic course in Eton Dorney. He continued through the Rowing NZ pathway after joining Waikato Rowing Performance Centre in the summer of 2011–12. Caleb was selected in the U23 men’s coxed four in 2012 and the crew won bronze at the World Rowing Championships in Trakai, Lithuania. In 2013 he was selected to cox the U23 men’s eight that won back-to-back gold medals in 2013 and 2014 at the World Rowing U23 Championships. Later in 2014 he coxed Hamish Bond and Eric Murray in the men’s coxed pair that won gold at the World Rowing Championships in Amsterdam, setting a new world-best time in the process. In 2015 he continued with the men’s eight as they stepped into the elite ranks, helping qualify the boat for the Rio Olympics with a 4th-place finish at the 2015 World Rowing Championships. The young men’s eight finished 6th in Rio. Caleb continued with the men’s eight for 2017 and 2018, and in 2019 went from the men’s to the women’s eight. He was a welcome addition to the crew and had plenty to offer. He lead the women to gold at World Rowing Cup III and a win at the Royal Henley Regatta. Caleb made history at the World Rowing Championships where he became the first male coxswain of a women’s crew to win gold in the eight. That win was also the first-ever gold for a New Zealand women’s eight.
At the 2020 Tokyo Olympics Caleb etched his name into the history books as the first male to win a women's Olympic Games medal after steering Ella Greenslade, Emma Dyke, Lucy Spoors, Kelsey Bevan, Grace Prendergast, Kerri Gowler, Beth Ross and Jackie Gowler in their silver medal-winning performance on the waters of Sea Forest Waterway.
Off the water, he has completed his Bachelor of Arts with the University of Waikato and is currently working towards his Master’s of Arts. He is a writer for Oarsport magazine, does other freelance writing work and is also a marriage celebrant.