From $450K to $9M ARR in 5 Years: Club Caddie’s Vertical SaaS Playbook
SaaS Interviews with CEOs, Startups, Founders
Release Date: 12/03/2025
How TeamSupport Reached $10M–$25M ARR With 1,000 Customers | Grant Stanis
SaaS Interviews with CEOs, Startups, Founders
How do you grow a customer support SaaS to over 1,000 customers and $10M–$25M in ARR in one of the most crowded software categories, without trying to outspend the giants on marketing? In this episode, Nathan sits down with Grant Stanis, CEO of TeamSupport. The company provides B2B customer support software used by more than 1,000 companies and generates between $10M and $25M in annual recurring revenue. Most customers start around $10,000 per year, but the best accounts expand significantly over time, including enterprise customers paying more than $1M annually. Customer support software is...
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From $7M to $70M Revenue: How RealDefense Scaled Through Acquisitions | Gary Guseinov
SaaS Interviews with CEOs, Startups, Founders
How do you rebuild a declining cybersecurity company into a $70M revenue platform with ~$25M EBITDA after buying it back for under $10M, while scaling primarily through acquisitions and debt instead of venture capital? Gary Guseinov is the CEO of Realdefense, a consumer cybersecurity and privacy platform that generates roughly $70M in annual revenue with $20–25M in EBITDA. Gary originally founded the business in 2003 as Cyber Defender, grew it to $70M in revenue, took it public, then later bought the company back in 2017 when it had declined to about $7M ARR. Today, Realdefense operates as a...
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How Ledge Reached $1M ARR with 24 Customers Paying $3K/Month | Tal Kirschenbaum
SaaS Interviews with CEOs, Startups, Founders
How do you build an AI SaaS company to $1M+ ARR with just a few dozen customers and raise a Series A at a 20x+ revenue multiple while competing against general-purpose AI tools? Tal Kirschenbaum is the Co-Founder and CEO of Ledge, an AI-native financial close platform helping finance teams automate the month-end close process. Just three years after writing the first line of code, Ledge has reached $1M+ ARR with ~24–36 customers paying roughly $3K per month, while targeting 300% year-over-year growth with a team of ~35 employees. What makes this story interesting is how narrowly the product...
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From $187M Ecommerce to $5M ARR SaaS: Spresso’s Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
SaaS Interviews with CEOs, Startups, Founders
How do you turn a failed public ecommerce company into a $5M ARR enterprise SaaS platform serving ~$2M+ contracts — while rebuilding with capital efficiency after bankruptcy and avoiding the growth-at-all-costs playbook? In this episode, Nathan sits down with Jared Yaman, co-founder of Spresso and former founder of Boxed, the bulk ecommerce company that scaled to $187M in revenue before its IPO and eventual Chapter 11 restructuring. Today, Jared leads Spresso, the enterprise ecommerce software platform spun out of Boxed, now serving roughly 15 enterprise customers worldwide and growing ARR...
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He Turned Pickleball Software into a $3M/yr SaaS
SaaS Interviews with CEOs, Startups, Founders
How do you turn a niche offline sports business into $3M in contracted ARR across 200 locations, while raising $8M and keeping pricing simple on a per-unit basis? Ben Borton is the Co-Founder of PodPlay Technologies, a vertical SaaS platform powering pickleball and racquet sport venues. What started as internal software for his own ping pong spaces is now a $3M contracted ARR business serving 200 locations and roughly 2,000 courts, with ACVs ranging from $10k–$15k and an $8M Series A completed in 2025. This business is interesting because it didn’t start as software. Ben built PodPlay...
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Bootstrapping to $50M ARR in Vertical SaaS | Vantaca’s HOA Software Playbook
SaaS Interviews with CEOs, Startups, Founders
How do you build a vertical SaaS company to ~$50M ARR serving 6M homes — after bootstrapping to $5–10M without outside capital — and then 10x with a minority PE round instead of giving up control? Ben Currin is the CEO of Vantaca, a vertical SaaS platform powering community association management companies. Since launching in 2018, Vantaca has grown to ~500 customers managing 50,000 communities and 6M homes, scaling from low six figures in 2018 to ~$1M in 2019, $5–10M by 2022, and roughly 10x revenue since taking minority investment. This is not a trendy market. HOA management is...
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How to Scale to $12M ARR: The Serial Founder Playbook for Vertical SaaS and Agentic AI
SaaS Interviews with CEOs, Startups, Founders
How do you scale a vertical SaaS platform to $12M ARR while navigating the aggressive valuation overhang of 2021 and a founding team transition. Matt Spiegel is building Lawmatics into a dominant legal CRM by leveraging a serial founder playbook that prioritizes high ARPU and agentic AI over traditional SaaS metrics. Matt Spiegel is the founder and CEO of Lawmatics, a legal marketing and CRM platform serving over 2,000 law firms. The company currently generates over $1M in monthly revenue with an average ACV of $5,000. After raising $25M in total capital, Matt has maintained roughly 20%...
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How Dresma Hit $2M ARR With Usage-Based Pricing & AI-Powered E-Commerce Imagery
SaaS Interviews with CEOs, Startups, Founders
Siddharth Sinha is the co-founder and CEO of Dresma, an AI-powered platform helping global brands create studio-quality e-commerce imagery, videos, and localized content at scale. Launched in 2020, Dresma helps brands like Puma localize product imagery across markets using AI models, data intelligence, and automated workflows. The company now serves ~28 customers, generates ~$2M ARR, and has grown profitably with a lean team of 31 people. In this episode, Siddharth explains Dresma’s usage-based pricing model, how studio partnerships drive over 50% of revenue, and how the company...
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Bootstrapping to $5M ARR: How Kukun Scales SaaS for Banks and Fintechs
SaaS Interviews with CEOs, Startups, Founders
How do you grow a nearly $5M ARR SaaS with just 2 sales reps, while staying bootstrapped and capital efficient? Raf Howery is the founder and CEO of Kukun, a B2B property data platform powering white-labeled tools for banks, fintechs, and insurers. After quitting a $1M/year consulting role, he built Kukun to serve ~25 enterprise clients, each paying $10K–$50K/month. The team now processes ~500,000 property addresses monthly across a growing suite of data-driven products. What makes this business especially compelling is the dual monetization model: a B2C experience that acts as a PLG wedge,...
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Bootstrapped to $15M ARR: How Flipsnack Scaled Digital Publishing with SEO & $200K ACVs
SaaS Interviews with CEOs, Startups, Founders
How do you scale a digital document tool to $15M ARR with 28,000 customers—without raising a dollar of VC? Gabriel Ciordas did it by going deep on SEO, mastering self-serve onboarding, and closing six-figure enterprise contracts—all while owning 100% of the business. Gabriel Ciordas is the founder and CEO of Flipsnack, a digital magazine and brochure platform. Since launching in 2011, he’s grown the company to $15M in ARR, with 28,000 paying customers and a pricing range that spans from $16/month self-serve plans to $200,000/year enterprise deals. Flipsnack operates in a...
info_outlineGolf course SaaS founder Jason Pearsall shares how Club Caddie scaled from $450K to $9M ARR in 5 years, sold to Constellation Software (CSI), and keeps growing with 600+ golf courses paying ~$15K ACV. If you’re building vertical B2B SaaS, this is a masterclass in niche focus, capital efficiency, and smart deal-making.
Jason breaks down why he built an end-to-end ERP for golf courses, how he used data-driven outbound, review sites, SEO and “answer engine optimization” (AEO) to win market share, and what really happened during his CSI acquisition and long-term earnout. We cover pricing, ACV targets, GTM channels, fundraising vs. selling, and how to design a growth engine when your entire ICP is just 15,000 accounts.
In this episode, Club Caddie founder & CEO Jason Pearsall breaks down how he:
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Built a vertical SaaS ERP for golf courses after buying and operating his own club
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Scaled Club Caddie from $450K to $9M ARR in 5 years with ~600 customers and ~$15K ACV
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Raised just $600K before being acquired by Constellation Software (CSI)
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Structured a long-term earnout instead of a flashy headline multiple
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Used data-led outbound, review sites (Capterra, G2), SEO, and AEO (answer engine optimization) to win in a niche
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Built a target list of every golf course, including who runs it, what software they use, and when contracts expire
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Turned multi-course operator deals into 50–100 account wins from a single sale
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Organized his BDR + AE team to touch every account on a consistent cadence
What you’ll learn:
Founder story & capital strategy
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How Jason went from golf course operator to SaaS founder
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Why he raised only $600K seed and then chose CSI over closing a full Series A
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How he thought about risk, fatigue, and opportunity cost when deciding to sell
Revenue, pricing & margins
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How Club Caddie reached $9M+ in ARR with 600+ customers
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Why they target $15,000+ ACV / ARPO per golf course
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How complex, multi-venue golf facilities drive higher contract values
GTM, outbound and channel mix
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Why vertical SaaS is a data game when your entire ICP is ~15,000 accounts
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How his team touches every golf course every quarter, across multiple contacts
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The role of Google Ads, review platforms, trade shows, and word of mouth
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How they use multi-course operator consolidation as a growth multiplier
SEO & “Answer Engine Optimization” (AEO)
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Why traditional SEO became a priority post-acquisition
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How they implemented schema.org and structured data to win AEO
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How to intentionally show up when buyers ask ChatGPT and other answer engines for “best golf management software”
Acquisition & long-term upside
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Why Constellation Software was the right home for Club Caddie
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How a small cash component + long earnout can still be a huge win
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What Jason wishes he knew earlier about enjoying the journey, not just the outcome
If you’re a B2B SaaS founder, investor, or operator building in a niche vertical, this episode gives you concrete tactics for pricing, GTM, data strategy, AEO, and selling your company without killing long-term upside.