What this CMO is doing to schedule a new marketing approach

Senior VP marketing at Australian company, Deputy, shares how he's bringing fresh structure and ways of working to the fast-growing company

For someone who claims no natural affinity with scheduling, it’s surprising Brett Chester finds himself in the role of senior VP marketing for a fast-growth technology company focused on making rostering easier.

But it is through his own career experience Chester says he has developed an understanding of the client base of his company, Australian-born Deputy, and the pain scheduling can bring.

“Scheduling is not something that comes naturally to me,” Chester tells CMO. “When I was running a retail store many moons ago, I almost locked someone in the back of the store as I closed for the night because I didn’t go through my handwritten tattered checklist document. So I experience the pains our customers are facing every day.”

It’s been a long time since Chester worked in retail, having subsequently moved on to a series of marketing roles in technology companies. These eventually led him to relocate to Silicon Valley.

His role at Deputy kicked off in May this year, following a series of meetings with company cofounder, Ashik Ahmed. Deputy itself began life 13 years ago with the goal of simplifying the scheduling of staff across a range of industries using an app-based system that makes it easier for managers to connect with, manage, and pay their teams.

For Chester, the role at Deputy is the opportunity to work for a fast-growth Australian company with strong potential in a global market. He describes the marketing function he inherited as robust and mature in its processes at the bottom of the funnel, but with more work to be done elsewhere.

“We were and still are exceptionally good at capturing intent,” Chester says. “A lot of our effort over the last four months has been around structure and alignment, a well as flexing and creating new muscles we didn’t have before, in channels we haven’t even dreamt about.

“So we are looking for opportunities to challenge that status quo. The team has responded phenomenally well and our restructure is already bearing fruit.”

One of those new initiatives will be unveiled on 16 October in the form of a partnership with a well-known US-based sporting team.

“We’ve built over time a cutting-edge machine that is allowing us to collect bottom of the funnel leads really easily and quickly,” Chester says. “The machine is operating at maximum capacity the whole time. But what we are missing is how we educate folks, and how we get in front of them and tell them that they have a problem they need to be aware of.”

Much of Chester’s thinking is guided by the success he has seen B2C marketers achieve using digital tools – something he is keen to emulate in his own B2B organisation.

“The phenomenon of account-based marketing really is fundamentally rooted in understanding who it is that you are selling to and giving them the message they need to hear to understand and get to that ah-ha moment as quickly as possible, at which point they will be moved into your sales cycle,” Chester explains. “B2C has been a leader in this type of thing for a very long time. And it is high time B2B SaaS businesses started leveraging and thinking more like these high-velocity businesses in B2C and really taking their approaches on-board.”

Rallying behind customers

Deputy itself saw a contraction of activity amongst some of its clients through the pandemic, as retailers and hospitality employers themselves scaled back the use of their app as they cut shifts and reduced their workforces. In response, Deputy launched the Gift a Shift program.

“We have raised about $122,000 for shift workers across Australia who have been struggling to find their next meal,” Chester says. “So there has been an obvious dip in the market as far as employed hours. But at the same time, we are at an important inflection point for hospitality where we need to start rallying behind our customers and start growing their community.”

Chester says many businesses are gearing up for growth as the world moves out of lockdown. At the same time, Deputy has witnessed greater interest in other sectors such as cleaning, healthcare and logistics.

“One of the challenges for marketing is to understand what phase of the adoption curve that vertical is in, and then speak to that vertical in that phase,” he says. “One of the verticals we go after is healthcare. That is a more traditionally oriented industry type versus hospitality, which is faster moving and more experimental. It all comes back to understanding your customer and talking to them in the right language at the right time.”

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