How 300,000+ Entrepreneurs Got Their Weekends Back

Feeling like there’s never enough time in your day? Still running your construction or service business with sticky notes, spreadsheets, and endless phone tag?

In this episode of Titans of the Trades, host Ryan Englin sits down with Sam Pillar, CEO of Jobber, a software platform that’s helping over 300,000 home service pros grow and reclaim their time. From that first customer with a lawnmower hanging out the trunk to managing over 10,000 jobs booked through AI receptionists, Jobber is making massive waves in the field service industry.

Listen in as Sam shares:

• The early days of Jobber and the big problem they set out to solve.
• How AI, automation, and modern tools are changing the game for blue-collar entrepreneurs.
• The #1 barrier to growth for trades businesses and how to fix it.
• Why investing in leadership skills matters as much as investing in tools.
• The emotional toll of “letting go” when your business starts running without you.

If you’re a construction or trades leader looking to grow your business without burning out, this episode is a must-listen.

Takeaways with Time Stamps

• 1:30 - Why a small electrical contractor sparked the idea for Jobber.
• 3:15 - The harsh truth: big software companies weren’t built for small business.
• 5:45 – Jobber’s new AI-powered features that help small teams scale faster.
• 7:50 - Real impact: 200,000+ AI receptionist conversations, 10,000+ jobs booked.
• 8:50 – The biggest barrier to growth for small contracting businesses.
• 13:30 – A lawnmower in the trunk to 7 trucks: the $MM story Jobber helped build.
• 16:50 - You don’t have to sacrifice family for business success.
• 20:10 – What happens when the business depends on people you don’t trust yet.
• 24:20 – The mindset shift: From “no one can do it like me” to “they can do it better.”
• 27:30 – Where to find Jobber’s free tools, business graders, and industry insights.

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/

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