Timing upsells: pain- and time-based rules

In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar interview Roland Ligtenberg, Co-Founder and SVP of Growth & Innovation at Housecall Pro, to break down how vertical SaaS can scale in messy, offline markets. Roland shares how Housecall Pro grew from a $4-per-month scheduling tool into a platform with more than a dozen products, emphasizing the importance of sequencing “layer cake” monetization — building a solid core before adding new revenue streams. He walks through unconventional customer acquisition tactics like cold-calling trades businesses, Yeti giveaways, truck-wash offers, and word-of-mouth tracking, all rooted in one principle: speak to customers through the channels they already use. The conversation also hits pricing strategy, PLG vs. SLG balance, TAM turnover, and using AI to tailor messaging by segment, trade, and intent — with constant A/B testing to avoid generic “AI slop.”

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SPONSORS:

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

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LINKS: 

Mostly Metrics: https://www.mostlymetrics.com

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Housecall Pro: https://www.housecallpro.com/

Roland on LinkedIn: https://www.linkedin.com/in/rolandal/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

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RELATED EPISODES:

Do vanity plates bring serious business?

https://youtu.be/Cm1rubFb-kg

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TIMESTAMPS:

00:00:00 Preview and Intro

00:01:37 Sponsors – Metronome, Pulley

00:03:57 Guest Introduction: Roland Ligtenberg

00:04:30 Poker Background

00:07:22 EDM and Hobbies

00:08:35 Layer Cake Strategy

00:09:19 Avoiding Too Many Layers Too Soon

00:10:13 Marketplace Pivot & Home Services Complexity

00:11:06 Early Fintech & Core Payment Rails

00:11:53 Source-of-Record Wedge

00:12:23 Serving 55+ Home Service Verticals

00:13:52 Pricing & Packaging Across Many Products

00:14:32 Core Plans and Add-On Structure

00:16:05 Balancing PLG and SLG

00:17:47 When to Begin Upsell Conversations

00:18:52 Sales, Onboarding & Success Motion

00:19:49 Matching Pain to the Right Solution

00:21:54 Finding the “Front Door” for Offline Trades

00:23:26 Gatekeepers & Communication Challenges

00:24:23 Unconventional Acquisition Tactics

00:26:27 Early Days Tactics for Traction

00:26:49 Cold Calling as First Principle

00:28:19 Improving LTV & Scaling Calling Ops

00:29:40 TAM Management & Value-Led Outreach

00:32:17 Word of Mouth as a Growth Driver

00:34:09 AI’s Role in Go-To-Market Personalization

00:38:04 AI Tools in the Growth Stack

00:40:18 Business Blunders Segment

00:43:20 Pricing in the Real World (Christmas Tree Story)

00:46:50 House Call Elf Holiday Marketing

00:46:58 Closing

#MostlyGrowthPodcast #VerticalSaaS #GoToMarket #PricingStrategy #FintechMonetization