“This was our first truly formalised one-to-one coaching program and the response exceeded expectations," explained Stephen Robinson, Head of Learning at Pepper Money.
"The engagement, the feedback, and the demand for more told us immediately that we’d tapped into something our senior leaders genuinely needed," he continued.
Pepper Money is a leading non-bank lender founded on a mission to help people succeed. It has provided flexible lending solutions to more than 500,000 customers throughout Australia and New Zealand for over 25 years. With its offering including home loans, car loans, asset finance, personal lending, SMSF, and commercial real estate finance.
At Pepper, effective leadership has always been a priority. As the organisation continued to grow and roles became more complex, it became clear that the expectations of its senior leaders were evolving.
“Leadership has always been a focus for us,” said Stephen. “But as the organisation matured, we recognised that our senior leaders were at a different stage in their development journey. Many had already completed multiple development programs."
"What they needed next wasn’t more training. Rather, it was dedicated time and structured support to focus on their own leadership.”
These leaders are experienced, capable, and often deeply tenured, with many having spent decades in the industry. Others are newly appointed into senior roles, navigating broader accountability, increased executive exposure, and higher expectations.
What emerged was not a skills gap, but an opportunity to create a protected space for reflection, recalibration, and continued growth as leaders.
Participant
Pepper Money
Pepper Money has clear leadership principles, including a strong commitment to coaching. “We know that mentoring is a very different skill set to coaching,” Stephen noted.
“We emphasise coaching as a key principle; instead of simply instructing our leaders. We aim to provide them with firsthand experience of effective coaching practices," he continued.
Pepper Money partnered with Hellomonday to pilot its first formalised one-to-one leadership coaching program for senior leaders. The program began with just two participants.
“The engagement and feedback from the pilot were enough to tip us over,” said Stephen. “We knew very quickly that this was something worth scaling.”
What stood out from the outset was Hellomonday’s flexibility and partnership approach.
“It was one of the simplest vendor process I’ve ever experienced,” Stephen said.
“Nothing was a problem. The question was always “what are you trying to achieve, and how can we make this work for you?”
Rather than enrolling leaders into a group-based program, Pepper Money made a deliberate decision to offer one-to-one coaching. This created a sense of exclusivity and ensured participants had uninterrupted space to focus entirely on themselves.
For many, it was their first experience of professional coaching. “Unlike mentoring, coaching guides you to find your own answers,” one participant shared.
“But you need to be clear on what you want to get out of it. Once I worked that out, the value was enormous,” they continued.
To date, 41 senior leaders at Pepper Money have undertaken Hellomonday’s one-to-one coaching programs, completing a total of 173 coaching sessions.
Participants came from across the organisation and represented a broad mix of experience, tenure, and functional expertise. Some had spent 20 to 30 years in the industry. Others were stepping into senior leadership roles for the first time.
“That confidentiality mattered,” Stephen noted. “People could talk honestly about challenges, pressures, and aspirations without feeling like they had to perform.”
The program fitted seamlessly into Pepper Money’s hybrid working environment, with leaders attending sessions across Sydney, Parramatta, interstate and offshore locations. Coach matching was another strength, with participants appreciating the ability to work with coaches who brought different perspectives, styles, and lived experience.
The results from the program demonstrate both depth of impact and strong demand for continuation:
The most common areas of growth included: greater self awareness, improved resilience, stronger collaboration, and more effective communication.
For many leaders, the impact showed up in subtle but powerful ways.
“The changes aren’t seismic,”one participant reflected. “They’re small adjustments in how you think, interact and respond. But those changes compound over time.” Others highlighted the value during periods of transition.
Participant
What began as a pilot has quickly grown into multiple cohorts. Midway through the first program, Pepper Money committed to a second round, now underway, and is actively exploring a third.
Crucially, participation has never been mandatory.
“The success has been driven byword of mouth,” Stephen said. “People talk about the value, nominate others, and actively ask to be involved. That’s exactly what we wanted.”
Hellomonday’s reporting and insights have supported Pepper Money’s learning strategy by providing clear data on impact while preserving participant confidentiality.
Pepper Money’s long-term ambition is to make one-to-one coaching available year-round, ensuring senior leaders have access to support when they need it most.
At Pepper, Hellomonday has helped turn leadership intent into action. As Chief Human Resources Officer, Sue Kent said;
“The Hellomonday coaching program has had a powerful impact at Pepper. Our people felt supported, challenged in the right ways, and better equipped to lead with confidence and purpose. It’s been an excellent investment in our leaders.”
