Jason Pearsall

9 statements across 1 episodes · 4 bullish · 2 bearish · 1 people on the record · first statement Dec 3, 2025 by Jason Pearsall · across every show →

On the record as a speaker too: Jason Pearsall's record, appearances and statements → this page counts the times other people say the name.

Everything said about Jason Pearsall, 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 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
Assertion Not checkable as stated
Pearsall: Club Caddie Deal Has the Longest Earn-Out in Constellation History
“I have the longest earn out in CSI history.”
Jason Pearsall Dec 3, 2025 ▶ 13:06 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 neutral
Disclosure
Pearsall: Club Caddie Development Began in 2015 to Solve Golf Course Operations
“Then, in operating our golf course, recognized that there wasn't a SaaS solution that was designed to handle a club, you know, like we had purchased and started, started building a SaaS solution in 2015 that became Club Caddy, and it's Club Caddy today.”
Jason Pearsall Dec 3, 2025 ▶ 1:29 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Dec 3, 2025 positive
Insight
Pearsall: Answer engines can find any product with schema markup
“Golf course, every product can be found by answer engines if they have a schema.”
Jason Pearsall Dec 3, 2025 ▶ 23:11 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 negative
Insight
Pearsall: Internal case studies are easily cooked; real proof requires third parties
“It's too easy to cook the books on like a case study, right? So the real validation comes from, you know, golf courses. We have no relationship with having that same success and then being able to demonstrate that that is a formula we can repeat elsewhere.”
Jason Pearsall Dec 3, 2025 ▶ 6:01 From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
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