He was competing in the dairy industry awards for the second time and also won three merit awards, including the TH Enterprises Ltd leadership award, the PrimaryITO "power play" award and the Westpac financial management and planning award.
After completing a bachelor of commerce in agriculture degree at Lincoln University in 2015, Redmond worked for a year as a herd manager at Rakaia, before moving to Culverden for a second-in-charge position.
He moved down the road to his present job two years ago as the farm manager at the Craigmore's Landsend farm, milking 830 cows on a 232ha farm.
Redmond previously entered the dairy industry awards in the farm manager category for the experience, while in the second-in-charge position.
"It was about meeting a few people. You can't really win as a 2IC and I had only just started farming.
"So I decided to have a proper crack at it this year. The awards process has helped me to benchmark myself against other managers and meet new people."
Redmond said he saw the training and development of his staff as a top priority, alongside protecting the environment and animal welfare.
He was also working through getting the farm certified with "Lead with Pride" by Synlait to ensure best management practice.
"We have most of it in place already, so it's about having the records.
"It doesn't take much to do our recording as it's on an app. If you put on an application of effluent, you get your phone out and make a note of what you are doing.
"It's not like you have to go home at night and write a big report. And then you can pull it out when you do your farm environment plan audit with Environment Canterbury."
This year, the farm added a third dairy shed and reduced the cow numbers by 200, which had paid off with the herd on target to produce 470kg of milk solids per cow for the season, up from 410kgMS/cow last season.
"I've got things set up how I want to run it now, so when it was the start of calving it was all go," Redmond said.
"It's easier on the staff, as they don't have to start at 3am. We're now in the paddock at 4.30am and have the cows in the shed by 5am."
He is married to Mel, who is a rural bank manager.
Redmond took part in the Canterbury/North Otago Dairy Industry Awards winners' field day on April 11 at the Darfield property where share farmer of the year Ruwan Wijayasena contract milks.