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How to use AI to answer your phones.
An interview with Jordan Gal, Co-founder & CEO of Rosie.
Bryan Shankman
April 10, 2025
Welcome to this week’s edition of The Workbench, a resource-rich weekly newsletter and podcast for home services entrepreneurs.
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Welcome back to The Workbench, the resource-rich newsletter for current and aspiring home service business owners. Today, I'm joined by Jordan Gal, founder & CEO of Rosie, an AI-powered answering service helping small businesses never miss a call.
Jordan's entrepreneurial journey - from bootstrapping million-dollar companies to raising venture capital and pivoting into AI - is packed with practical wisdom, insights, and plenty of lessons learned.
The 7 Key Takeaways
Below are the 8 most essential insights from my conversation with Kent that you can apply to your home services business today.
1. Embrace your Entrepreneurial DNA
Many of us in home services come from backgrounds rooted in family businesses or independent ventures. Jordan’s experience highlights the importance of understanding yourself and leveraging your unique background - your own entrepreneurial DNA - to confidently pursue your own journey.
I’m an immigrant and grew up in an immigrant entrepreneur household. Watching your parents come from another country and decide not to work for anyone else directly led to my inability to work for other people. I literally quit Wall Street as soon as the bonus hit my bank account.
2. Make something people want
Jordan’s success with CartHook was rooted in clearly identifying real pain points from business owners expressing frustration online. For home services, understanding customer frustrations in your local market can similarly unlock growth. Listen carefully to customer signals - then build solutions that directly address them.
I went into Facebook groups full of frustrated e-commerce store owners. They were constantly asking, 'How do I sell like ClickFunnels but process the orders and inventory in Shopify?' They were basically yelling out exactly what product they needed. So we built it, and it grew extremely quickly
3. Be wary of building on another platform
Building your business exclusively around someone else’s ecosystem (whether a CRM, franchise, or another platform) can provide initial traction but also serious risk.
Diversify your customer acquisition and integrations to ensure your business isn’t overly dependent on one powerful partner.
Shopify didn’t like us peeling a billion dollars a year out of their checkout flow. Eventually, they crushed the company. It was a terrible experience. The platform wants success for themselves, not for you. If you're aligned with their success, you'll have a good time—but go into it with clear eyes.
4. Embrace new markets
AI and new technologies can open opportunities for home service companies and their suppliers. Keep your eyes open for genuine innovation - especially those solving previously unsolvable problems. These can create valuable differentiation in your market.
AI creates a rare situation where a big problem exists without 100 existing solutions - because solutions weren't possible before. SMBs historically had just two phone options: voicemail or answering services. AI now offers a third, better option. It felt like an insane opportunity
5. AI doesn’t need to replace humans
Home service businesses regularly lose potential customers to missed calls, especially after hours or during peak busy times. Jordan team initially thought their AI answering service, Rosie, needed to replace human receptionists.
They soon realized their true competition was voicemail, which most callers immediately abandon. Even an AI solution that's not perfect still significantly outperforms missed calls.
We initially thought we had to replace human receptionists, but we realized quickly we're actually competing against voicemail. Everyone hangs up on voicemail, so even a solution that's 80-90% good, like Rosie, already provides massive value compared to missed calls.
6. Avoid shiny objection syndrome
It’s tempting to add new services or features prematurely. Jordan’s advice: If you’re already growing steadily, be patient. Focus on consistent execution, listen carefully, and let your customers guide your next big move.
Right now, Rosie is growing really fast. I constantly remind myself: we don't actually have to add anything new yet. What makes me think we do? We're still picking up breadcrumbs from customer comments and insights. We shouldn't rush into a direction - let the market tell us what's next.
7. The resurgence of SMBs
Home service entrepreneurs should recognize a positive shift: SMBs and home services are gaining increased respect, support, and attention. Embracing this momentum can lead to new partnerships, growth opportunities, and improved status in your community.
It’s so fun working with SMBs again. Status around home services and SMBs is rising. Private equity and big money are paying attention. Leaving Harvard to start a painting company is seen as a smart, cool thing to do. It feels exciting to be part of a healthy, growing community
Looking Ahead
Jordan’s approach to building Rosie highlights an important lesson for every home service business owner: prioritize clarity, flexibility, and market-driven patience over rushing into premature expansion.
While Rosie continues to hone in on solving the painful voicemail problem for SMBs, Jordan remains open-minded about where the company might go next - whether that’s deeper integrations, expanding to become a full-fledged phone management platform, or something else the market reveals.
For home service entrepreneurs, this reinforces the wisdom in staying close to your customers, carefully observing their needs, and allowing those insights to naturally guide your next big strategic move.
I'm not sure exactly what direction Rosie will ultimately take, and that's intentional. Right now, Rosie is already growing really fast doing exactly what it's doing. I constantly remind myself that any new direction should be guided by clear signals from our customers, not just from our own assumptions. We're still picking up breadcrumbs from customer comments and insights, and I want to be patient enough to let the market tell us what's next.
Wow! You made it to the end; thanks for sticking with us.
The full interview is available on YouTube below, Spotify here, and Apple Podcasts here.