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December 2, 2025 57 mins
Welcome back to Disciplined Troublemakers. In this episode, host Scott Shagory engages with Steve Benson, the CEO and founder of Badger Maps, a leading mobile mapping solution tailored for field sales professionals. Steve’s journey from tech sales to becoming Google Enterprise’s top sales executive reveals the vision behind establishing Badger Maps in 2012. From a modest beginning, he has grown the company into a global SaaS powerhouse, boasting over 90 employees and an impressive $8 million in annual recurring revenue.

Scott and Steve share an insightful conversation about the realities of scaling a SaaS business without the backing of venture capital. They discuss how actively listening to customer feedback helped shape Badger Maps' unique niche in the market. Steve also sheds light on the significance of memorable branding—yes, it often involves an animal!

This episode offers valuable insights on remote team dynamics, achieving product-market fit, and the merits of steady growth over the rapid pace often associated with VC-funded ventures. Founders, CEOs, and anyone interested in sustainable technology growth will find pragmatic lessons and candid reflections throughout their discussion.

Chapters:

00:00 - Introduction
00:19 - From Sales to Software Startup
06:00 - Naming Trends in Tech Branding
08:14 - Global Team Structure Insights
12:37 - Classic SaaS Success Journey
14:18 - AI Success and Scaling Challenges
19:28 - Strategic Decisions and Market Insights
23:52 - Building Differentiation Through Hard Work
25:51 - Focus Over Ego in Business
30:47 - Sales Mapping and Territory Tools
33:34 - Bootstrap Success Through Customer Focus
34:46 - Competing in Mapping Solutions
40:58 - Tech Priorities: Team, Product, Growth
44:10 - Strategic Foundations for Sustained Growth
46:59 - Early Entrepreneurship and App Building
49:35 - Bliss in Ignorance
52:54 - Incentives Shape Outcomes
56:29 - Outro

Quotes:

"Identify a niche and deliver real value. With software's extensibility, steady growth and customer focus can lead to lasting success."- Steve Benson

"Consistency in serving customers is key. Stay true to your vision, listen carefully, and you'll create something truly impactful."- Scott Shagory

Key Takeaways:

Solve Problems You Know Deeply
Creativity Isn’t Always About Reinventing the Wheel
Steady, Sustainable Growth Can Win the Race
Listen to Your Customers—And Build Moats Around Their Challenges
Know Your Strengths and Stay In Your Lane
Bootstrapping vs. VC: There’s No One-Size-Fits-All Path
You Will Grow, Even If You Don’t Expect To
Endurance Builds Brands That Matter

Connect with Steve Benson
LinkedIn: https://www.linkedin.com/in/stevenbenson/
Instagram: Steve Benson (@stevebensonsf)
Website: Badger Maps - Route Planner for Sales

Connect with the Host Scott Shagory
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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