Picture this: You’re running your field service business from your truck, bouncing between job sites, and your phone never stops buzzing. Estimates, invoices, missed calls, and that never-ending pile of admin work waiting at night.
Sound familiar?
Sam Pillar, CEO of Jobber, knows this world all too well. In this episode of Titans of the Trades, Sam shares how Jobber went from helping a single electrical contractor to powering over 300,000+ service pros, many of them in construction, landscaping, HVAC, painting, and more.
The Problem: Time Poverty
One of the biggest takeaways from this episode is how time, not money, is often the biggest bottleneck for growth. That’s why Jobber was built: to automate the admin, streamline communication, and give business owners margin to lead.
And today, they’re not just digitizing paperwork, they’re leading the charge with AI tools that:
- Book jobs via automated receptionists.
- Auto-generate review requests and email campaigns.
- Build professional websites in a click.
- Respond to voice commands on the go.
This isn’t “tech for tech’s sake.” It’s practical. It’s usable. And it’s designed for the boots-on-the-ground business owner.
The Emotional Side of Letting Go
Another powerful moment? Sam addresses the emotional challenge of letting go as your business starts running without you. Many founders wrestle with feeling “useless” when the team no longer needs them daily. But as he explains, that’s actually the goal: building something that thrives without relying on your every move.
Still, people problems remain the #1 reason small businesses get stuck. Jobber’s most successful users are the ones who embrace leadership, build clarity, and trust their teams to deliver.
Rags to Riches: The Stories That Inspire
Sam shares a story about a high school kid in Atlanta who started with a lawnmower and his mom’s car. Today? Seven trucks. Multi-million dollar business.
Another user was able to visit his dying parent across the country. Without the business falling apart. That’s real impact.
Success isn’t just about revenue. It’s about freedom. Margin. Time with family. And Jobber’s platform gives contractors the tools to unlock that freedom.
The Big Lesson: Don’t Wait Until You’re “Big Enough”
One of the biggest myths in the trades? That software systems are for companies with 10+ employees.
Not true.
In fact, Sam argues the opposite: The smaller you are, the more you need this. That’s when you’re strapped for time, when every minute counts.
Whether it’s automating estimates, following up on reviews, or just making sure a customer isn’t lost to voicemail, Jobber gives small businesses leverage that used to only be available to the big guys.
Ready to Scale Smart?
If you’re stuck in the field, buried in admin work, and tired of missing dinner with your family, here’s your sign. Systems are what set leaders apart from laborers.
Head over to getjobber.com and explore:
- Their free blueprint tools.
- Business graders and audit tools.
- The latest Gen Z trades insights report.
And when you’re ready to sharpen the axe? Start building a business that doesn’t depend on you for every decision.
Tune in to the full episode for the inspiration, tools, and real-world stories that could reshape your future.
Connect With Sam:
Website: https://www.getjobber.com/
LinkedIn: https://www.linkedin.com/in/sampillar/
Jobber Tools: https://www.getjobber.com/free-tools/
Jobber Blueprint: https://www.getjobber.com/blueprint/
Jobber Home Service Community: https://community.getjobber.com/
Support Titans of the Trades
If you found this episode insightful, please subscribe, share, and leave a review for Titans of the Trades. Your support goes a long way in helping us bring more impactful discussions your way.
