The Pitchside Report

PitchUp is powering participation and access in sport

Last quarter, we set out a bold vision, building the one-stop shop to find, book, and play sports in Australia.

This quarter brought more milestones, along with more lessons that will shape how we grow from here.

🔮 From Vision to Validation

• Growth is real: We’ve now surpassed 1,000 total users on the platform and are consistently generating booking and SaaS revenue each month.

• Early product-market fit signals: Our recent product updates are driving higher engagement and usage with schools.

• Runway is steady: We’re managing expenses carefully to extend our cash runway while preparing for our seed raise.

📈 Key Metrics

🙌 Wins (Goals + xG)

• AI breakthrough: Our new MVP booking agent successfully completed test bookings on two major enterprise council systems — 6x faster than ChatGPT-5 which will support previously ‘non-bookable’ venues aiming to increase the utility & stickiness of the platform.

• Our next steps are to validate user demand via a live AI-booking assistant MVP. You can try it yourself here!

• New schools traction: We welcomed schools in QLD + VIC, with growing inbound interest from others.

• Community impact: We hosted Kick for a Cause, raising $3,000 to support Justeen Kruger, Australia’s Deaf National Goalkeeper, ahead of the 2025 Deaf Olympics.

• SaaS adoption: SaaS revenue has grown 150% this quarter, confirming school demand.

⚠️ Misplaced Passes (+ Learnings)

• Magic 10: Despite striking a promising partnership with an international academy run by ex-FC Barcelona players, not enough tickets were sold to make the inaugural masterclass happen. The learning: define clear expectations and deliverables in future partnerships with downside mitigation to protect our reputation and interest with schools

• AI video outreach didn’t stick: Our video-led AI outreach campaign to Brisbane Catholic schools underperformed. Schools ignored the noise. The learning: double down on direct, personalised, founder-led outreach – school leaders are time-poor and need to see value demonstrated upfront to commit to a demo

🧗‍♂️Current Challenges

• Sales Cycle Length: This remains a challenge with schools moving slowly (~3 months from intro to contract). We’re building a larger pipeline and running several new lead capture and qualification experiments to offset this.

• Tech Capacity: With a small team, we’re having to be ruthless in prioritising the execution of our product roadmap and managing school expectations and requests along the way.

• Department of Education schools: There are encouraging signs of support from both federal and state governments – for example, Victoria recently announced a pilot involving 41 schools to make more basketball courts available, backed by $1.4M in funding. However, the initiative currently appears to lack clear points of ownership at the school level, and some schools we’ve spoken to are not even aware of their role in the program! Significantly, no software solutions have yet been explored as part of the pilot, with funding focused on additional staffing. This presents both a challenge in navigating government-led initiatives and an opportunity for PitchUp to demonstrate how technology can enhance and scale these efforts.

⏭️ Looking Ahead

Next quarter, we’re focused on:

• Launching live AI-booking for users.

• Expanding SaaS adoption in schools.

• Converting early traction into momentum for our seed raise.

🙋 How You Can Help

We’re actively seeking:

• Investors for our upcoming seed round.

• Partners for AI-booking pilots with councils, venues, and schools.

• Advisors & connectors with experience in government procurement and education technology.

Join us in unlocking every court, oval, and field across Australia (and beyond!) by clicking here 👈

💡 From the Founders

When we started in 2023, our “why” was clear: unlock every sporting facility and make booking as easy as playing the game itself.

Back then, AI was a whisper and “agents” lived only in 007 movies. We sketched the vision over a “cuppa”, see below. Today, it’s unfolding step by step - from 1,000 users to AI booking breakthroughs - and we’re only just getting started.

In the meantime,

Play well!