Club Caddie
15 statements across 1 episodes · 5 bullish · 1 bearish · 1 people on the record · first statement Dec 3, 2025 by Jason Pearsall · said 16 times in 1 episodes since 2025 · across every show →
Mentions by year
brought up most by Jason Pearsall (10)
tap a year for its mentions
2025 16 mentions in 1 episode
Everything said about Club Caddie, oldest first
Dec 3, 2025 bullish
Dec 3, 2025 neutral
Pearsall: Club Caddie raised only $600K prior to Constellation acquisition
“I only raised 600 K before the CSI acquisition. We raised a 600 K seed round that got us to about 20 19. In 2019, I started fundraising a series A and spent about 15 months getting check commitments and almost had the round closed and then Constellation came i…”
Dec 3, 2025 negative
Pearsall: Sold Club Caddie after 15 months of exhausting VC fundraising
“I was running around spending time with investors and not in the operations of my business, and the business was doing well, and I didn't think we had good processes, and I wasn't involved in the, you know, in solving those problems because I was more worried …”
Dec 3, 2025 bullish
Pearsall: Multi-course operator consolidation enables 100-course SaaS enterprise deals
“Multi-course operators has been another fuel of our growth is that there's been a lot of consolidation where we can win one deal and win a hundred accounts where in the past, you know, you haven't been able to do that. You're, you know, one multi-course operat…”
Dec 3, 2025
Pearsall: Club Caddie touches every target golf course every quarter
“We touch every golf course, every quarter a different contact point within that golf course too. It's not always The one person that you reach out that makes the decisions and tells, you know, so it's important to go wide and deep in the organization.”
Dec 3, 2025
Dec 3, 2025 neutral
Dec 3, 2025
Dec 3, 2025 positive
Dec 3, 2025 bullish
Dec 3, 2025 positive
Pearsall: Club Caddie has captured a couple dozen leads from ChatGPT
“I know that we have now added within HubSpot is the lead source and origin source, and there's been a couple dozen this year that have come in through it. But you know, we just started tracking it within the last six, seven months.”
Dec 3, 2025
Pearsall: North America has 15,000 golf courses and 8,000 match Club Caddie's ICP
“For us, there's 15,000 golf courses in North America. Seven, 8000 are within our ICP, you know, ultimately three to four contacts per golf course. There's 35,000 people that we need to get in contact with multiple times a year.”
Dec 3, 2025
Dec 3, 2025 neutral
Pearsall: Early club SaaS lacked depth while legacy server software dominated
“There were mature solutions for full clubs, not just like a golf course with a point of sale and a
Tea sheet, but needing, you know, events and weddings and restaurants and dining reservations and all kinds of other, other apps as well. There were mature solut…”
Dec 3, 2025 neutral
Pearsall: US backlog is more valuable than expanding into Canada
“Conversion rates aren't entirely favorable for SaaS companies, and so when you have pent up demand, the most valuable dollars are coming from the U.S., and so, you know, it doesn't make sense to take on Canadian clients, and we have a backlog of U.S. Clients t…”