The engineer who learned to sell, then became CRO

“I had a silly preconception… that sales is kind of not real.”

That’s not the type of admission most Chief Revenue Officers make publicly. Yet Jonathan Staff shared this early career observation matter-of-factly.

Long before executive leadership, podcasts and helping shape conversations around Australia’s AI infrastructure future, Jono was an engineer. And like many engineers, he viewed sales with scepticism – commercial teams created promises, delivery teams inherited the consequences.

Looking back, he laughs at how little he understood. This is a leader who has evolved from questioning the value of sales to redefining what commercial leadership really looks like.

“It was mostly from a place of ignorance,” he reflects.

“I didn’t understand the business side of tech. I didn’t understand the role that sales had to play, and what salespeople actually do. As an engineer, you often don’t really see it. You don’t have an appreciation for that side of the business. Usually they just bring you more headaches to deal with and more customer problems.”

That admission is the foundation of a much bigger story.

Jono’s journey from network engineer to Group CRO at ASE Tech – a Sydney-based managed service provider (MSP) – is not one of leaving technical thinking behind. Quite the opposite.

In fact, engineering is one of his greatest commercial advantages. More importantly, it reshaped how he thinks sales should be practised and why the technology industry continues to overlook some of its best future commercial leaders.

The engineer who didn’t believe in sales

Ask Jono why he left an established executive role as Head of Private Cloud at Macquarie Technology Group to join ASE Tech and he smiles… “I turned 40 and had a brain snap.”

The humour masks what was actually a carefully considered evolution.

Technology has been the only industry that Jono – who is also Executive Director of WinDC, an AI infrastructure start-up – has ever known.

While completing high school, he studied network engineering through TAFE before receiving a New South Wales (NSW) Government scholarship to continue his studies. Jono’s career started out as a systems administrator, before eventually becoming an enterprise architect responsible for major infrastructure before deciding he no longer wanted to spend nights pulling apart data centres.

“I decided I didn’t want to be ripping out servers and data centres at two in the morning anymore,” he shared.

Project management became the obvious next step. It also became the bridge into something he never expected.

At BlueFire – one of Australia’s early MSP innovators – Jono joined during a period of rapid growth as the business expanded from roughly $9 million to $30 million before being acquired by Dimension Data in 2012. The buyout exposed him to large-scale services businesses, acquisitions and commercial growth that would shape the rest of his career.

One conversation changed everything. His mentor, Sonya Moray, saw something he couldn’t yet see himself.

“Jono, you know a lot about delivering this stuff. Have you ever thought about selling it?”

The engineer inside resisted.

“It took a while for Sonya to convince me,” Jono admitted.

Because like many engineers, this technical specialist simply didn’t believe sales was where the real work happened.

Discovering that sales is both science and art

Looking back however, Jono believes the biggest obstacle wasn’t capability. It was culture and once again, back to that “silly preconception” – shared by many in the engineering community – that sales is kind of not real.

That mindset still exists across much of the industry today because many engineers see sales as disconnected from technical reality.

Salespeople create complexity. Engineers solve it.

Jono understands that perspective because he once shared it. What changed wasn’t his technical knowledge, however – rather an understanding of the commercial side of technology.

The breakthrough came through an old-school salesperson who fundamentally changed how he thought about the profession.

“Sales can be distilled into a science and an art,” Jono observed.

“For someone with an engineering mindset, everything clicked. The cool thing about it being a science and an art is that you can learn the science while you develop your art.

“It’s kind of like the way a comedian can write a great joke. Two comedians can tell it. One bombs and the other kills it. The structure of the joke is the science – anyone can learn it. But to make it really funny, you’ve got to tell it the right way.”

Sales, Jono argues, works exactly the same way.

There are frameworks, disciplines and repeatable behaviours that anyone can learn. The artistry comes later through experience.

“As someone coming from that engineering background, I found comfort in that,” Jono acknowledged.

“I could just show up every day and follow the rules. Make the calls. Do the work. Something would happen. I’d be okay. Then I’d gradually get better at the art.”

That distinction continues to shape how he leads sales organisations today.

Learning to embrace winning (and losing)

For Jono – who co-hosts the Things. Reasons. podcast alongside Naran McClung – one of the biggest adjustments moving from engineering into sales wasn’t learning how to sell. It was learning how to lose.

“In engineering it’s very hard to tell if you’re a great engineer or an average one,” Jono noted.

“It’s subjective. When you move into sales, it’s binary. You either win or you lose. You make the number or you get fired.

“That reality intimidates many technically minded people and I must admit, it intimidated me too. You’re never actually okay with it. You’re always wondering where the next deal is coming from. You never feel like you’ve arrived.”

For Jono, there are broadly two types of people that exist in the profession – those who run away from that pressure and those who somehow run towards it.

“For some people, that anxiety propels you forward,” he added.

“You’re competitive. You want to achieve. Other people just run for the hills. My own career has been driven as much by curiosity as competitiveness. Sales is a game. If you’re going to play the game, then the point is to win.”

Every salesperson remembers their first failed deal and Jono remembers his vividly.

Ironically, it involved a used-car dealership. The young sales gun drove across Sydney expecting contracts to be signed. Instead, the potential customer informed him that the owner had changed their mind.

Initially, it felt like failure. Later, his mentor reframed the entire experience… “you didn’t lose the deal, you never had the deal.”

Jono realised he had broken one of the rules his mentor constantly reinforced.

“I let him tell me what I wanted to hear and I wasn’t talking to the right person,” Jono recalled.

“But rather than blaming the customer, I blamed the process. I broke the rules. That lesson stayed with me because if you lose a deal and you’ve still followed the rules, then you did everything you could. You’re not going to win them all.”

It remains one of the defining philosophies of his leadership today.

Results matter. Discipline matters more.

The power of project managers and engineers

In drawing on more than two decades of market experience in Australia, Jono believes one of the industry’s biggest misconceptions is that engineering prepared him for sales. It didn’t. Project management did.

“The science of project management and sales are very similar,” he explained.

Every project begins with a mandate. There are stakeholders. Risks. Milestones. A clearly defined outcome.

Throughout the project, good governance constantly asks one question. Should we continue? Or should we stop?

Jono realised great sales opportunities follow exactly the same pattern.

“A sale is the same thing,” he continued. “There’s a critical path. There are stakeholders. There are risks. You need a plan. You need to keep qualifying whether you’re still heading where you thought you were.”

That structured thinking removed much of the uncertainty engineers often associate with selling. It simply became another operating framework.

As a result, Jono has become increasingly convinced that the technology industry is overlooking enormous commercial potential.

“I don’t think the industry has great pathways for engineering talent to break into sales,” he challenged.

“I believe technically minded professionals already possess many of the capabilities exceptional solution sellers require. The role of a great solution salesperson is a translator.

“That means understanding something deeply technical before explaining it simply enough for business leaders to make confident investment decisions. You need that foundational knowledge because it helps establish credibility. But you also need the science and the art. The art form is in the translation.”

Jono’s own career reflects that philosophy.

“I’m a better salesperson than I was an engineer,” he added.

Not because he abandoned engineering. Because he applied engineering thinking somewhere new.

Curiosity as a competitive advantage

If there is one characteristic that quietly connects every stage of Jono’s career, it is curiosity.

“If I have a question, I must answer it,” he laughed. “My friends often describe me as being full of useless facts but I just need to know.”

Technology. History. Politics. Philosophy. Geography. Space. It hardly matters.

“I’m endlessly curious,” Jono assessed.

That same curiosity eventually extended beyond technology into psychology, leadership and business. It also explains why he deliberately seeks discomfort.

For example, launching a podcast in Things. Reasons. Speaking publicly. Building relationships. Growing a personal profile.

This is all despite describing himself as an introvert.

“A lot of what I do is to make myself uncomfortable,” Jono shared. “It annoys me if I’m scared of something that shouldn’t be scary. I can do it but it depletes my battery.”

Like many leaders, people often mistake confidence for extroversion. Jono sees them as completely different things.

These days Jono no longer measures success purely by deals won. Helping others succeed has become equally rewarding.

“I’m more in a phase of my career where I’m helping others do it,” he added.

“I describe myself as a player-coach. Someone happy to jump onto the field when needed, but who increasingly enjoys building winning teams. I love putting the team together and winning the game.”

That philosophy appears in the cadence he has established with every sales organisation he has led – Monday meetings establish commitments while Friday meetings review outcomes. Everyone contributes and everyone is accountable.

“I see sales as a team sport,” Jono expanded.

Not everyone enjoys the process initially, however.

“Some people love it but some people are reluctant,” he admitted. “But they still show up because eventually they realise someone else might learn something from what they’ve just done. Knowledge compounds when people choose to share it.”

The second half of the journey

As Jono reflects on more than two decades in technology, surprisingly few regrets emerge. This is a leader proud of the path he has taken – “I’ve had a very good career. I’ve made very deliberate moves and taken calculated risks.”

The lessons he wishes he’d learned earlier are more personal than professional. Health. Relationships. Perspective.

Following a health scare five years ago, he stopped drinking alcohol altogether.

“I would have focused more on my fitness and my health,” he accepted. “I would have also appreciated networking much earlier and leaned into making relationships earlier.”

For someone who naturally describes himself as introverted, it has become one of the biggest shifts in his career. Today, those relationships continue opening unexpected doors.

“I’m finding this now… having an abundance mindset,” Jono outlined. “Being relaxed about doing good things for other people with no expectation of anything in return. But trusting that it does come back in some way.”

Looking back across more than 20 years in the industry, Jono no longer sees networking as collecting contacts or building influence. This is actually about consistently leaving people better than he found them.

“It feels like 20 years of just doing the right thing,” he recalled. “Now the doors just open everywhere.”

It is a fitting conclusion for someone who spent the first half of his career engineering technology before spending the second half engineering trust. Because perhaps Jono never really stopped thinking like an engineer.

Instead, this is a Group CRO that simply began applying that same curiosity, discipline and systems thinking to people, leadership and commercial strategy instead of servers. And, as he has discovered, those systems can be every bit as rewarding to build.

“My advice? Just leave good energy in your wake.”