At 24, Wilkinson has had several career highlights already, coming first in both the Red Bull Foiling Generation NZ Series and Red Bull Foiling Generation NZ Series in 2016. He also placed second at last year's Oceanbridge NZL Sailing Regatta.
Wilkinson became Ngaroto's first world sailing champion in 2013, winning the Red Bull Youth Foiling Catamaran series, and was a member of the 2017 NZL sailing team at the youth America's Cup in Bermuda where they finished second.
Wilkinson and Dawson are the only Olympic newcomers in the initial sailing team announcement, further crews will be considered for selection to the New Zealand Team following a series of upcoming world championships.
It is quite a turn-around for Wilkinson.
Nine months ago he was sitting at home wondering what life was going to look like.
He and Dawson have been working together in the foiling multihull for less than a year.
Wilkinson was previously partnered with Liv Mackay in the Nacra 17, but Mackay's now teamed with Jason Saunders, still in the Nacra.
Dawson, on the other hand, had previously raced in 49erFX boats. But with Rio silver medallists Alex Maloney and Molly Meech the custodians and incumbents in the boat, she was unlikely to get a look-in.
Wilkinson and Dawson subsequently decided to link.
"Ian Stewart, the high performance director for Yachting New Zealand, was trying to get us into it and we just thought, 'let's have a crack'. And now we're here, it's amazing," says Wilkinson.
"We just work well together, learn well together and get on well as friends, and we don't bring a lot of ego into the boat.
"We're there to have fun and learn, and somehow we've ended up here."
But coming together wasn't as simple as just transferring the already established skills they had.
Wilkinson's moved from steering to crewing, while Dawson's done the reverse. In layman's terms, he points the boat in the right direction, while she controls the sails.
"She's got strong and turned herself into a machine, and I've had to learn the fine intricacies of steering," Wilkinson says with admiration.
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Wilkinson is honest, though. He knows he and Dawson still have a long way to go if they're to improve on their seventh-placed finish at this year's world championships in Geelong, and be in contention in Tokyo.
"The hard part with sailing is when it's really windy and wavy, and we haven't mastered that yet. So we'll have to do some time in waves, maybe go to the west coast or go to Japan and just get used to being in big, gnarly conditions.
"That's our biggest weakness. In the lighter stuff, we've developed well, but if we can smash it in the breeze, that'll be really helpful."
At a time where numerous events around the world are being postponed or cancelled because of coronavirus, Wilkinson and Dawson will soon head overseas.
"We're off to Spain for the first event of the European season. Off the back of the worlds, we're keen to test ourselves again, we feel like we're learning fast, so it's another opportunity to figure out where we are," says Wilkinson.
New Zealand has a proud Olympic sailing legacy, having collected 22 medals since the first gold won by Peter Mander and Jack Cropp in the Sharpie class in Melbourne in 1956.
The Tokyo Olympics run from July 24 until August 9.
