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 →

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brought up most by Jason Pearsall (10)

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Everything said about Club Caddie, oldest first

Dec 3, 2025 bullish
Disclosure
Pearsall: Club Caddie ARR is a little over $9M
“Yeah, pretty close. Little over that.”
Jason Pearsall Dec 3, 2025 ▶ 7:29 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 neutral
Assertion Supported
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…”
Jason Pearsall Dec 3, 2025 ▶ 10:03 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 negative
Disclosure
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 …”
Jason Pearsall Dec 3, 2025 ▶ 15:05 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 bullish
Assertion Not checkable as stated
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…”
Jason Pearsall Dec 3, 2025 ▶ 17:00 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025
Disclosure
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.”
Jason Pearsall Dec 3, 2025 ▶ 20:00 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025
Disclosure
Pearsall: Club Caddie generated $450K in revenue in 2019
“Yeah, our revenue was only 450,000 in twenty-nineteen.”
Jason Pearsall Dec 3, 2025 ▶ 12:14 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 neutral
Insight
Pearsall: Scaled Operations Are Easier but Less Fulfilling Than Early Building
“Enjoy the journey. I always wanted the outcome to get to where we're at, you know, now, and truthfully, like, the days are easier now, but they're not as fulfilling and they're not as fun.”
Jason Pearsall Dec 3, 2025 ▶ 27:15 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025
Insight
Pearsall: Golf courses function as multiple small businesses under one profile
“And so the complexity of a golf course is that it's many small businesses and one that all have to operate and communicate together under a single customer profile.”
Jason Pearsall Dec 3, 2025 ▶ 3:24 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 positive
Assertion Not checkable as stated
Pearsall: Club Caddie Generates $15,000 Average Revenue Per Golf Course Location
“They're higher than that. And so on average, we look for about an average of 15,000 ARPU per unit.”
Jason Pearsall Dec 3, 2025 ▶ 2:48 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 bullish
Disclosure
Pearsall: Club Caddie has 600 customers, adding 25 monthly in winter
“600 and growing by about 25 every month.”
Jason Pearsall Dec 3, 2025 ▶ 6:19 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 positive
Assertion Not checkable as stated
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.”
Jason Pearsall Dec 3, 2025 ▶ 24:51 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025
Assertion Not checkable as stated
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.”
Jason Pearsall Dec 3, 2025 ▶ 21:23 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025
Assertion Not checkable as stated
Pearsall: Club Caddie is earliest-stage acquisition in Constellation's history
“We are the earliest stage company that Constellation's ever acquired.”
Jason Pearsall Dec 3, 2025 ▶ 12:56 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 neutral
Assertion Not checkable as stated
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…”
Jason Pearsall Dec 3, 2025 ▶ 4:52 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 neutral
Insight
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…”
Jason Pearsall Dec 3, 2025 ▶ 6:49 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
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