Some people know me as Leigh Sherman, others know me as Coach Leighroy.
I’m the founder of Hillspeed Group, an international coaching company and product lab that merges my background in elite sport with my experience in high growth tech companies.
Hillspeed is built on the same principles we use to develop elite athletes in sport because that's where my story starts.
/ Coach Leighroy /
I went from athlete.
Competed at elite level in triathlon and swimming, and my vision was to represent my country.
But at some point, that dream felt out of reach, burnout set in, my training habits changed, and I began questioning how my development as an athlete could have been different.
To coach.
That led me to study sports science, where I spent years working alongside Australia’s top sports scientists, coaches, and administrators.
Back to athlete.
Eventually, my career shifted from sport to retail, then to digital businesses and startups.
🔶 By 2010, I was winning hackathons and building startups.
🔶 By 2014, I built a VC-backed tech startup.
🔶 By 2016, I moved to Berlin as one of the first Australian’s to go to Techstars, a tier-1 accelerator.
“I had built something my customers loved, but I was suffocating under the weight of growth → stuck in a game I was never prepared to play.”
The crash.
By 2018, I had exhausted my resources, my team and my mental health. I had to stop.
It took 6 months to get the customers off my platform because they were small businesses and relied on our infrastructure.
“Like many founders, I lost my company, my stability, and my identity → life went to 0 in all areas.”
The dark side of startups.
It became obvious to me that all founder were injured on some level (to use a sport metaphor).
In sport, injuries are part of the game, you address them. Pro athletes know this.
In the startup world everyone wants to avoid the tough conversations with founders and share some form of “just run faster” advice.
We can do better.
A certified sports coach has a fiduciary responsibility to prevent their athlete’s from injury.
In the startup ecosystem I realised nobody held that level of accountability for the founder game.
The real problem to solve.
The way founders are left to synthesise advice is the problem.
It takes 10-20 years to develop the pattern recognition to own your own development as an athlete.
That’s why in sport we have science and protocols for working with young athletes.
“We need to fundamentally improve the way we support founders like you to step into your potential for scale.”
Back to coach.
Between 2018 and 2020 I built the Company Model framework while working inside scale-up companies Zwift.com and Booking.com
Then I switched into education and training and worked for industry giants such as Jack Delosa, Dan Martell, and I studied coaching under one of the top 5 life coaches on the planet Benjamin J Harvey.
Time to be a coach again!
Commitment to my athletes.
Coach Leighroy has been my professional alias since 2022.
A reminder to myself and a commitment to you that I’m here to win with you, at speed, without burnout.
I live on the Northern Beaches of Sydney, Australia, with my beautiful family.
I work with athletes all around the globe, from North America to India.