Surviving Outside Sales

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!

Surviving Outside Sales is a business podcast hosted by Mike O'Kelly, with 388 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Mike O'Kelly hosts Surviving Outside Sales, a business show with 388 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #388

  Outside Sales Reset | SOS Ep. 388

  Aug 17, 202621 minS1

  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 real scheduling failure caused by broken connectors between platforms • why a full CRM and website tech audit matters for trust and pipeline • what retail sales being down signals for fall selling and resistance • how inflation and higher interest rates change buyer behavior • selling like an investigative reporter through stronger discovery questions • creating clarity and calm to reduce uncertainty and prevent stalled deals Just email me, mike@survivingoutsides.com, or connect with me on LinkedIn and shoot me a message there. Support the show To connect with the show: Subscribe, Download & Share! Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!! Connect with Mike: Mike@survivingoutsidesales.com LinkedIn: Mike O'Kelly | LinkedIn Check out your career path at: https://survivingoutsidesales.com ______________________________________________________________________ If you are looking for outside sales career clarity, go to: Surviving Outside Sales Scorecard

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  Episode #387

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

  May 18, 202628 minS1

  <p>Send us Fan Mail</p><p>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. <br/><br/>• treating your sales territory like a business with a clear process <br/>• using the house analogy to build in the right order <br/>• leveraging AI as a tool without outsourcing your skill <br/>•...

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  Episode #386

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

  May 4, 202621 minS1

  <p>Send us Fan Mail</p><p>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. <br/><br/>• the widening gap between reps who improve and reps who repeat old habits <br/>• building a sales territory like a small business with real principles <br/>• a real-world shock that wipes out 55% of revenue overnight <br/>• why “vibes” selling and blanket clai...

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  Episode #385

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

  Apr 24, 202631 minS1

  <p>Send us Fan Mail</p><p>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.<br/>• why we keep the intro consistent and focus on being a real resource over chasing views<br/>• how AI in sales should amplify skill rather than replace it<br/>• what weak preparation looks like in interviews when answers come from...

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  Episode #384

  Three Outside Sales Skills That Outperform Any AI Tool | SOS Ep. 384

  Apr 13, 202631 minS1

  <p>Send us Fan Mail</p><p>We cut through the AI noise and get back to what actually wins in outside sales: practiced skill. We break down the three abilities buyers test for and why tools can support your process but cannot replace your presence.<br/>• AI as an accelerator rather than a replacement for outside sales<br/>• Why skill development beats “education” and sales hacks<br/>• Knowing what questions to ask to frame the deal<br/>• Knowing what to listen for so you do not chase noise<br/>• Responding with confidence as the real separator<br/>• Using role play and repetit...

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