Australian enterprise deals over $1 million in total contract value now involve upwards of 10 buyers and a sales cycle approaching 300 days. If your sales motion still depends on the founder being in every room, you are building a ceiling, not a company.

About the guest

Jonathan 'Jono' Staff is Chief Revenue Officer at ASE Tech and Executive Director at WinDC. He has spent more than 20 years building high-performance sales teams across Australian IT, including time at AC3, Dimension Data, and Macquarie Cloud Services. He also hosts Things. Reasons., the independent show for Australian IT leaders.

What this episode covers

• The 2026 Australian buying landscape: more stakeholders, longer cycles, and why the cost of poor qualification has never been higher

• Why 92% of B2B buyers begin their journey with vendors already in mind, and what that means for how you get in front of them

• The science and art of sales: why high performers are not following the playbook, and why that matters for founders building a team

• Why 'I'm a relationships guy' is the wrong answer in a sales interview, and what credibility actually means to a modern enterprise buyer

• How to know when founder-led sales has become a ceiling, and what to do before you make your first sales hire

• The right hire sequence: stabilise the customer base first, separate landing from retention, and never hire a Swiss Army knife

• Why performance managing through incentive plans is a trap, and how to set a new hire up so you can have an honest conversation if things go wrong

• Quick Fire Three: one GTM decision to revisit in the next 30 days, one piece of sales advice that has aged badly, and the first sign the sales motion is working

Why now

The spray-and-pray era is over in Australian B2B tech. Buyers are more educated, more committee-driven, and more discerning than they were two years ago. The cost of a failed sales hire has never been higher, and most founders are still trying to scale before they have extracted their own process. This conversation gives founders a practical framework for getting it right before they burn capital on the wrong hire.

Who this episode is for

• Scale-up founders with $1M to $10M ARR who are trying to move beyond founder-led sales

• Revenue leaders stepping into an early-stage or growth-stage B2B tech business

• Investors and board members evaluating the quality of a portfolio company's go-to-market

• Operators building or inheriting a sales function in Australian tech

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#RuleOf40 #AustraliaTech #FounderLedSales #B2BSales #TechScaleup

In this first episode of Rule of 40, Jason Serda and Josh Ayscough introduce the podcast and unpack the "misunderstood middle", the critical stage where startups must evolve into real, scalable businesses.

They explore how today's tougher funding environment demands discipline, resilience, and a focus on building sustainable companies, not just raising capital. This episode also introduces the Rule of 40 as a key metric for balancing growth and profitability.

A candid look at what it really takes to scale and why most companies get stuck along the way

In this episode of Rule of 40, Jason Serda and Josh Ayscough get practical on one of the most important questions for scale-up founders: how do you know if your business is actually heading in the right direction?

They make the case that undisciplined growth is dead. The era of raising capital to paper over execution problems is over, and founders now have one crack at getting it right. Key topics include:

• Burn multiple, net revenue retention, and payback period — the three metrics that matter most and why tracking the direction of travel matters as much as the number itself.

• Why most founders report these metrics without tracking whether they are improving or deteriorating quarter on quarter.

• The rubric: Jason's defined operating framework that keeps founders executing to a plan rather than managing by instinct.

The episode also goes into bridge funding and what separates a bridge that leads somewhere from one that doesn't. Specifically:

• What investors are looking for when founders come back to market for a bridge round.

• How to tell the difference between a double shuffle with a clear destination and a delay that amplifies existing problems.

• Why more capital into a business with deteriorating metrics makes things worse, not better.

A practical guide to scaling with discipline and building the kind of business that stands up when investors look closely.

Follow Jason Serda on LinkedIn: Jason Serda | LinkedIn

Follow Josh Ayscough on LinkedIn: Josh Ayscough | LinkedIn

Listen on Spotify: Rule of 40 on Spotify

Watch on YouTube: [Insert Link]

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