Rudman shot to fame with a thrilling silver medal at the Turin Games back in 2006 as a 24-year-old, stopping the clock in 2:01.06 to finish behind only Maya Pedersen-Bieri.
But the Pewsey-based athlete is now turning her attention to the next generation of Winter Olympic talent, with 20-year-old Pittaway marking herself out as a promising young star after a brilliant gold at the 2016 Winter Youth Olympics in Lillehammer.
The German-born ace followed that up with bronze in the 2019 World Junior Championship and Rudman, who also won senior World Championship gold in St. Moritz in 2013, reckons the precocious Pittaway is destined for greatness.
"Ashleigh is really good and a really talented girl," Rudman said.
"She was out at the Youth Olympics in Lillehammer, where she won gold, and she's a really nice girl who has a smart head on her shoulders.
"She's a really, really naturally gifted driver of the track, and I think if she can improve on her push start so it's competitive with the world's top five, then she will be flying, and really one to watch.
"Ashleigh's the main one to look out for but there are a few guys coming through who are already in the World Cup, and I think they'll be ones to watch.
"Guys tend to be a little bit slower than the girls coming through, in skeleton, but I think there are definitely a few to watch.
"They're yet to really unleash themselves, but it is quite hard, as when you're at the lower echelons in the sport it's completely sporadic in our sport.
"In places like the UK and Canada, there's a really good team behind athletes and you can develop really fast."
The British women enjoyed a scintillating Winter Olympics last time out in Pyeongchang, as Lizzy Yarnold and Laura Deas both finished on the podium along with Jacqueline LÃ¶lling.
Yarnold reigned supreme by just 0.45s on the South Korean ice as Germany's LÃ¶lling finished second, with Deas crossing the line in an overall time of 3:27.90 to scoop bronze.
That made it back-to-back golds for Yarnold after success at Sochi 2014, while GB were also crowned queens of the ice in Vancouver as Amy Williams ascended the top step on the podium.
Rudman's silver came four years before that but almost a decade and a half on from that memorable Italian Job, she says the future of British skeleton is in safe hands.
"I hope that skeleton's got a bright future in the country - we've definitely got a great system in place, where they're bringing in lots and lots of new athletes through," she added.
"At the moment, there have been quite a few retirements so there's a new crop of athletes coming through, but skeleton have got such great investment and can really accelerate programmes fast for the athletes.
"They can bring athletes through to an Olympic performance level quite quickly, which a lot of other sports would be desperate for.
"We're really, really lucky, and the young athletes are all really good and happy, and as long as they can continue that then we'll be in a good position."