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Podcast Blog: The Brutal Truth About Being a Start-Up CEO

Before Waze, before Google Maps, field sales reps were literally printing out MapQuest directions, juggling paper calendars, and plotting customer visits using highlighters and guesswork.

It was clunky. It was wasteful. And Steve Benson had seen enough.

In this episode of SaaS That App, Steve joins host Aaron Marchbanks to talk about how he built Badger Maps, a smart, simple SaaS tool that optimized everything about how field sales teams plan and execute their routes. It’s a story of right-place-right-time intuition, customer-validated growth, and bootstrapped grit. But more than that, it’s a real-world case study of how you build enduring software when you really understand your user.

From Google to the Road

Steve didn’t stumble into sales tech; he lived it. After cutting his teeth in sales at IBM and HP Autonomy, he spent four years at Google, where he worked on the Maps API and enterprise tools like Gmail and Docs. That’s where it clicked.

“I was managing Google Maps API sales in the Western US, and I was so keenly aware of sales problems and of the Google Maps API and what it was capable of.”

That chaos looked like reps printing MapQuest directions, managing paper calendars, manually mapping customer visits, and trying to fill more efficiency into their week.

One App to Rule the Road

The MVP was straightforward: put customer data on a map viewable on a mobile device. That’s it.

“At first, it wasn’t even connected to a CRM. Just a CSV upload into a mapping environment.”

But the vision was clear: make field sales mobile-first, map-centric, and stupidly simple.

The early results were immediate. Sales reps could now see their entire territory at a glance, plan optimized routes, and prioritize visits based on geography and CRM data. Was it more efficient? Absolutely. But it also saved hours of driving and admin every week.

As smartphones matured, so did Badger Maps. Native apps replaced browser-based tools. CRM integrations replaced flat file uploads. Route optimization, data filtering, and great features like the “lasso tool” (to quickly select a group of customers) became standard.

But none of this was done in a vacuum.

Built With Customers, Not Just for Them

Steve didn’t code the app himself. His superpower? Talking to customers.

“In the early days, I spent an unbelievable amount of time just talking to users. Not just to fix bugs or collect feedback, but to understand their real problems. That’s what shaped our roadmap.”

In some cases, those customer conversations turned into deals before a feature even existed. That’s how Badger built trust and ensured it was always solving the right problems.

Surviving the Platform Risk

Of course, there were risks. Badger Maps was built on Google Maps tiles. What happens if Google pulls the plug or jacks up prices?

“At first, we were definitely dependent. However, over time, alternative providers emerged. We’re no longer locked in.”

Another major challenge? Talent. It’s brutally hard to build an engineering team in expensive parts of the US. Big Tech sucks up so much of the talent.

The solution? Go global. Steve found amazing people all over the world: Eastern Europe, Asia, Africa. If you’re bootstrapping, you have to play the global hiring game. You won’t survive otherwise.

When to Spin Out a Product

Eventually, Badger faced another common SaaS dilemma: What do you do when a side feature becomes so powerful it deserves its own life?

Enter Grid Squid.

Steve built it because they needed a better way to sync with CRMs. The commercial options were either too brittle or too broad. They built a solution for themselves and then realized this could help a lot of companies.

So they spun it out. But Steve is clear: don’t split your focus unless the use case demands it. If you’re bootstrapped and growing 40% per year, don’t chase shiny objects. Stay focused unless the new thing is that compelling.

The Hard Truth About Startups

Steve doesn’t sugarcoat the startup life. This isn’t a job. It’s not a side project. It’s a commitment that takes almost all your bandwidth.

“You can’t be super involved in your community. You’re going to make sacrifices.”

But if you survive long enough to get the train rolling? It’s hard to stop.

Steve also has advice for aspiring founders: only tackle problems you really understand. You’re going to be in this for a long time. It helps a lot if you’ve lived the problem yourself.

Final Thoughts

Steve didn’t try to reinvent CRM. He didn’t chase buzzwords or build for the VC pitch deck. He just watched a sales team wrestle with paper maps, saw a better way, and built it.

Today, Badger Maps serves thousands of salespeople, has nearly 100 employees, and generates $8M+ in ARR, all without outside funding.

Great SaaS doesn’t start with a pitch. It starts with solving a real problem for a real person, then doing that over and over again, better each time.

Steve’s Background

Steve Benson is the Founder and CEO of Badger Maps, a pioneering platform that helps outside sales teams optimize their routes and increase productivity. With a vast background in sales leadership at companies like Google, IBM, and HP, Steve has spent over a decade developing software solutions that address real-world challenges faced by field sales professionals. Under his leadership, Badger Maps has grown to 92 employees and expanded its offerings to include Badger Sales University and Grid Squid.

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