The Pitchside Report

Read the latest PitchUp updates - for our investors, first-believers and customers alike. Enjoy!

State of Play (Halftime - June 2025)

We returned from Melbourne this week, where we attended the National Sports Conference with key industry thought leaders from both sport, government and technology (that’s us 🙋‍♂️)

We came away with three key takeaways:

  1. Sport is running out of space to play

  2. Sport is evolving, both in the way it’s played and in the needs of those playing it

  3. PitchUp must also evolve, from creating more space to play to thinking about how that space is found and interacted with.

So, in this halftime (year) update, we’ll cover exactly that:

How PitchUp is changing its focus from being just a community hire management tool for schools to building the digital infrastructure of sports access.

A Strategic Shift: From SaaS to the Skyscanner for Sport

Michael, from 30,000ft (where he does his best thinking). I wonder how much an office altitude chamber costs 💡🤔 😅

“What if we stopped selling software to schools… and instead became the aggregator where team sports come to search, find and book any sports venue”

Incidentally, we’d recently been introduced to a key leader in this space (ex-Canva, Typeform and Skyscanner), so we promptly set up a meeting on our return to explore this pivot and find out what we don’t know.

🧠 What We Learned (+ what we’re doing about it)

Agentic booking is the booking logic of the future. Instead of a user manually booking a venue, what if they could simply say:

Hey PitchUp,

Find an indoor futsal court near me, that’s open after 6 pm and has parking. 10 of us want to play tonight!”

And it doesn’t matter if that court is a managed by PitchUp, a school, or a council. That’s agentic booking.

And that’s exactly what we’re building next!

→ A centralised, trusted search platform for sports venues;
→ Venue discovery + booking across schools, councils, and clubs;
→ Natural language voice and text search.

Prototype we’re currently testing with a select group of Clubs

🎯 Key Metrics & KPIs

Monthly booking revenue: $5k+

Monthly subscription revenue (from schools): $2k+

Venues listed: 120+

Gametime*: 600+ hours

*Participation hours created. This is new capacity, i.e. time or venues not previously bookable.

🙌 Wins

  • We welcomed 2 new team members this month, Paddy and May, who are already chipping away on PitchUp 2.0

Paddy O’Connor - Backend Software Engineer and Gaelic Footballer

May Thu - Frontend Software Engineer and AI-enthusiast!

  • We’re raising $10k to help Deaflympics athlete and Deaf Koala’s Goalkeeper, Justeen Kruger, to represent Australia on the World Stage!

Read more about Justeen’s story and make a donation here or pit your wits against her in our Penalty Kick Challenge at the Queensland Independent Schools Summit!

  • PitchUp addressed key government and sport stakeholders at the National Sports Conference last week and took home a share of the prize for the Most Innovative Program to help schools unlock their potential to impact sports participation.

Tom pictured alongside the other speakers from the AFL, Anglican Schools, and Phillips Coaching

🧩 Missed Opportunity

We were unsuccessful in our bid to pilot PitchUp’s community booking software with the South Australian Department of Education.

What we learned:

  1. We need to slow down and invest more time upfront to gain a deep understanding of the customers’ internal drivers and decision-making process before pitching.

  2. Strong interest from end users isn’t always enough; despite vocal support from several schools, the Department opted for a legacy international vendor with a longer track record (20+ years).

While disappointing, this was a valuable test of how we compete in institutional sales environments and where we must adapt our strategy.

🧗‍♂️Current Challenges

  • Listing 1,000+ sports venues (with structured, accurate venue data) over the next 30 days

  • Managing longer sales cycles with schools, now we’re outside of primary procurement windows (Term 1 and Term 4)

  • Navigating the complexity of building in compliance with ISO27001 (required by some schools before shipping)

🙋Asks

  • Seeking mentors and/or operators with experience building and shipping AI agents

  • Intros to anybody with experience in B2B sales with schools and meeting compliance requirements 

  • Warm intros to councils, education groups, or owners/operators of sports venues

That’s all for now. As always, we’re grateful for your support, and if we can help (return the favour) in any way, you know where to find us!

In the meantime,

Play Well

Tom

Mike