First CPO of booking platform talks about preparing his HR leadership for growth at scale
“Many years ago, when I first went into to HR, I wanted to be in HR because I knew I wanted to help people. And looking back now, that sounds so naïve,” says Greg Sheppard, Chief People Officer of booking platform Booksy.
“I started off in technology companies and software companies straight out of university. And I just kind of fell into that industry by chance, and I'm so glad that I did it wasn't by design.”
Although Sheppard spent nearly the first decade of his career in the commercial side of things, he says it was always about the “people connections” for him. An HR director who was something of a mentor helped him realize that human resources could enable him to make those connections with people while also having a strategic voice at the table.
Brilliant basics program gives HR a framework
At his previous role as CPO at Veeam Software, Sheppard developed what he calls his “Brilliant basics” approach to human resources structuring. He is bringing that ethos to Booksy, where he is part of a newly-minted executive team ushering the company into a new stage of growth – 2023 saw unprecedented revenue increase and Booksy has announced it will be “doubling down” on technology to continue that growth.
“’Brilliant basics’ is really about having a fundamental structure that supports the people and culture team,” he said. “It gives the people and culture team a framework to work across. A really effective business partner can only be super effective in being that trusted adviser to the business if everything behind what they do is in place.”
For HR that structure starts with onboarding, he says, and especially with getting the right talent into the top of the funnel. That means having an effective employer brand and compensation philosophy that will draw the right people to them.
Having a strong company narrative is an important aspect of Sheppard’s brilliant basics approach, and what he calls the “cradle to grave” journey of an employee’s career at the company.
“What do we want to be known on the market for? Are we going to pay people above market rate, or are we a mid-market company? Where do we peg ourselves, in terms of what sort of talent do we want to approach,” Sheppard said.
“We have the basis now of an employee value proposition. What do we want to be known as outside of Booksy? It's okay that we can have high NPS scores for our internal people, that we feel that we have strong employee engagement. But people outside, what do they know about us?”
In person HR team collaboration to build crucial connections
Sheppard is the first CPO at Booksy, which has presented unique challenges in harmonizing the HR team where there was disjointedness previously.
What Sheppard has found the most effective in achieving that goal – and the most exciting – is in-person relationship building which he says has been invaluable in fostering innovation and letting his leadership shine.
For his conversation with HRD he took a break from an off-site session with his leadership team in Spain, where they were strategizing their brilliant basics “roadmap” which had just received corporate sign-off.
“I've bought the entire team together here. Because now this is where the fun starts. This is where the actual work starts. This is what this week is for. They're really, really talented and they've got some great ideas in other areas and they're really creative,” he said.
“I'm having lots of these little epiphany moments. People are putting their hands up for stuff that are not normally in their wheelhouse, and it's just amazing because they're talking to each other in ways that they've never talked to each other before.”
Lifting up HR leadership for growth
As an example of the crucial role in-person collaboration has played in implementing his strategic plan, Sheppard described how during the off-site meeting an L&D specialist offered insight into the HCM product strategy, because in a previous role she had worked on automation tools. Because of that conversation, she’s now working on the HCM development team.
“That would never, ever have happened if we hadn't have all been together in a room, 35 of us, because I would never have known, and the gentleman that's responsible for running that project, who's on point for it, he would never have known that [she] has that skill, but also has that motivation and wants to help and do something outside of her own job. Because she knows that that's the route to growth.”
Shifting the HR team’s mindset from “start-up” mentality to one of growth and scale has been a big part of Sheppard’s first nine months. The best part, he says, is watching the team realize their own potential through this process, and showing them how to see the long-view and to be excited about the opportunities for their own professional growth.
“I realized very early on that wow, this is this is quite a large transformational project. And it's a mindset shift. And then actually, that got me even more excited because I don't really like easy jobs,” Sheppard said.
“I've been honored and privileged to be running this team for nine months now, and I can genuinely see actual fundamental change in the motivation and the mentality of the vast majority of this team. They are so psyched and vibed up for the rest of this off-site for the rest of this week. And I know that that is going to translate really well with the people and the teams that they look after.”
