Manchester-born bartender, Holly Grimshaw, didn’t set out with a grand hospitality masterplan – but once bars got under her skin, there was no shaking them. Now based in Sydney, Grimshaw has spent the past 2.5 years behind the bar at Maybe Sammy, carving out a career defined by commitment, curiosity, and a deep belief in team culture.
Her turning point came at Sterling, owned by the Schofield brothers, where she was exposed to a higher level of hospitality and mentorship.
“That was my first real hit of what this industry could be,” Grimshaw says. “Working with people at that level changed everything.”
What began as a teenage job quickly became a calling, fuelled by learning from people she considers among the best in the business.
Despite loving her role in Manchester, Grimshaw felt the pull of change – and sunshine didn’t hurt. Australia had long been on her radar, and Maybe Sammy was a name she’d heard whispered throughout her career. One interview with Sarah Proietti later, and she was behind the bar the following week.
“It just fell into place,” she says.
Since moving to Sydney, Grimshaw has noticed clear differences between the UK and Australian bar scenes. While the UK offers a wider spread of styles – from hotel bars to molecular cocktail dens – Australia, and Sydney in particular, leans into warmth and approachability.
“It’s more laid back here,” she says. “You walk into a bar and it’s ‘hey team, how’s it going?’ There’s less variety, but an abundance of hospitality.”
At venues like Maybe Sammy, that friendliness is paired with world-class execution. Her time at the award-winning bar hasn’t been easy – and she doesn’t pretend it is.
“It’s taken perseverance, dedication and commitment,” Grimshaw says. “But it’s easier when you truly love what you’re doing.” One phrase she’s taken to heart at Maybe Sammy is simple: time to push. Keep going, trust the process, and what’s meant to be will be.
When asked about advice entering the industry, Grimshaw is thoughtful rather than preachy. She believes that no two journeys are the same.
“You can’t compare your path to anyone else’s,” she says. “It hasn’t been easy, but you have to believe in yourself, know what you want, and enjoy it – otherwise, hospitality won’t give back.”
What’s kept her grounded is the team around her.
“Culture is everything, you join for the idea, but you stay for the outcome,” she says. “At Maybe Sammy, trust, support, and a shared passion for excellence are what hold the operation together – especially during high-pressure periods like the Maybe Festival season, where learning curves are steep and teamwork is non-negotiable.”
To Grimshaw, hospitality is more than a job. “You’re dealing with people,” she says. “You have to genuinely want to be there, to help people and create an experience.” That mindset extends to her personal tastes too – her go-to drinks are a cold, creamy pint of Guinness (which she insists is never quite the same in Australia) and a Miami Vice, a tiki classic she’s still hunting down in Sydney.
As for the future, Grimshaw keeps it refreshingly simple. “Over the next five years, my goal is to absorb as much knowledge as possible” she says. Becoming the best version of myself, while growing organically with Maybe Sammy, rather than chasing titles or timelines is what I strive to achieve.”
In an industry built on patience, pressure, and people, it’s a grounded vision – and one that feels right at home behind one of the world’s most celebrated bars. 