In this episode, Scott Ingram interviews Rich Strobel, the top sales performer at Smart Data Solutions in Minnesota. Rich shares an unfiltered look at his journey from selling car stereos as a teenager to leading strategic enterprise deals in healthcare technology. He opens up about the three pillars of his success—tactical empathy, a results-driven mindset, and the power of building a personal “C suite” of coaches and advisors.
Together, Scott and Rich dive deep into the realities of enterprise sales, the importance of internal and external relationships, and lessons learned from both soaring wins and painful setbacks. Rich reflects on his unconventional career path, the challenges of balancing family and professional achievement, and why intentionality—in both work and life—makes all the difference. Whether you’re just embarking on your sales career or aiming for that next level of mastery, this conversation is packed with actionable insights, hard-earned wisdom, and the kind of real talk you won’t find anywhere else.
Read the full transcript & show notes →
What We Covered:
[00:01:35] Rich’s top 3 sales success factors: tactical empathy, mindset, and relationships.
[00:05:29] How Rich became #1 at Smart Data Solutions.
[00:08:09] Recent sales numbers: $5.3M vs $4M quota.
[00:10:22] Early sales jobs—from Best Buy to selling books door-to-door.
[00:14:29] If he could do things over, what would he change?
[00:17:40] Favorite and most painful sales stories—including losing a huge RFP and closing a transformational $2.1M deal.
[00:26:21] The split between internal vs. external work in enterprise sales (60/40 or more internal).
[00:36:04] Strategic selling: aligning company initiatives with customer needs.
[00:46:52] What Rich struggles with: feeling overwhelmed and prioritization.
[00:49:23] A detailed day-in-the-life and productivity routines.
[00:54:36] Books and resources that have impacted Rich.
[00:59:08] The difference between loving the work and liking it every day.
[01:09:13] Foundational habits, mindset, and career intentionality.
[01:20:52] What Rich believes others might not—Why non-work life is business-critical too.
[01:26:35] Advice to new and mid-career sellers: investing in self and building your support structure.
[01:31:11] Rich’s actionable challenge for listeners.
Quotes:
“Action creates results, and it’s actually those results that create the inspiration and motivation to go deeper and longer.” [00:01:52]
“The support structure that you build around yourself is so very important… building out that team is a really critical part of it.” [00:02:32]
“If it was easy, it wouldn’t pay well. So let’s just figure it out.” [00:17:17]
“The relationships that you build inside your four walls of the organization… are critical.” [00:26:51]
“Trust but verify is one of the most critical guidelines that I can think of.” [00:19:54]
“I love it. That doesn’t mean I like it every day.” [01:00:58]
“Whatever makes things easier for one team almost always makes it harder for another team.” [00:28:29]
“If you’re good at what you do, you’re going to have recruiters reach out to you… every business has serious challenges once you get under the hood.” [01:09:55]
“Self care is not self-ish. You’ve got to protect the asset, and in this role, you are the asset.” [00:41:20]
“Know where you want to go, and then start putting the pieces in place to position yourself well for that.” [01:32:12]
Resources Mentioned:
- Never Split the Difference by Chris Voss
- Mastery by George Leonard
- The Confident Mind by Dr. Nate Zinser
- Megadeal Secrets by Jamal Reimer
- The Game (Podcast) by Alex Hormozi
- Chasing Excellence (Podcast) by Ben Bergeron
- Better Sales Networks (Harvard Business Review article)
- Amber Deibert – Mindset coach (newsletter and professional coaching)
- Jamal Reimer’s Wiser – SaaS solution for aligning sales with enterprise initiatives
Sponsors:
Sales Success Summit