Surviving Outside Sales | Podcast Guru

Details

Surviving Outside Sales is a podcast for outside sales pros that want to learn how to navigate the chaotic world of outside sales. Join host Mike O'Kelly as he shares his sales philosophies, biggest deals closed and some that got away during an award-winning, 20-year career, plus interviews with other sales experts from inside and outside sales, business owners who built something for themselves, as well as many other entrepreneurs. From building business process & systems that scale to landing the perfect sales job and hearing stories from entrepreneurs who have blazed a trail others can follow, it's all here!

Recent Episodes

The Three Cs For Tough Markets | SOS Ep. 389

Send us Fan Mail We’re resetting after a big life move and using that fresh-start energy to face the reality of a slower market without panic. We lay out a simple framework to help buyers feel safe enough to decide, especially as Q4 budgets tighten and uncertainty rises. • moving south and why a fresh start changes momentum • why the housing market ripples through the whole economy • how higher interest rates freeze buying and selling decisions • preparing for Q4 when ...

16 MIN

Outside Sales Reset | SOS Ep. 388

Send us Fan Mail We share a candid reset on what’s been happening behind the mic, including a family move, a messy tech breakdown, and why we’re refocusing on sustainable outside sales systems. We also zoom out to what a softer retail market and buyer volatility mean for your pipeline and why clarity is the skill that closes deals right now. • summer update and the decision to move from Charlotte to Fort Mill • why we care more about sustainable tools than quick wins • a rea...

21 MIN

AI Can’t Replace Skill, Process Still Closes | SOS Ep. 387

Send us Fan Mail I make the case that process, systems, and frameworks beat personality and “vibes” in outside sales, and AI only helps when the fundamentals are already in place. I share real examples from my own coaching journey and the bad cold outreach I see every week, then lay out how to do recon, ask better questions, and recover when deals slip. • treating your sales territory like a business with a clear process • using the house analogy to build in the right order ...

27 MIN

How To Build A Sales Territory Like A Business In 2026 | SOS Ep. 386

Send us Fan Mail We break down why outside sales feels harder in 2026 and why that pressure is a signal to level up, not a reason to panic. We share how to build a territory like a business, use AI without getting trapped by misinformation, and close with skill that still works when the market shifts. • the widening gap between reps who improve and reps who repeat old habits • building a sales territory like a small business with real principles • a real-world shock that wi...

21 MIN

You Must Learn to Sell Without the Tech | SOS Ep. 385

Send us Fan Mail We get blunt about the rising “skill gap” in outside sales and why leaning on AI as a crutch makes reps slower, weaker, and easier to replace. We lay out the real test of sales ability: can we walk into a meeting with zero tech and still control the conversation, handle objections, and close. • why we keep the intro consistent and focus on being a real resource over chasing views • how AI in sales should amplify skill rather than replace it • what weak preparation looks like ...

30 MIN