Surviving Outside Sales

Hosted by Mike O'Kelly

Business EntrepreneurshipInterviews guests

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Episodes

387

Latest episode

May 2026

Language

EN-US

About the show

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!

Listen to episodes

60 recent

May 18, 2026Episode 38727 min

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

Send us Fan MailI 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 • leveraging AI as a tool without outsourcing your skill • learning through failure and iterating fast as you grow • why walk-in pitches and info dumps get blocked • opening with questions and discovery instead of “me, me, me” • doing recon and gap analysis before a cold call • rehearsing your plan so you do not rely on vibes • avoiding hard sells and qualifying for fit • building leverage with tech, network, referrals, and content Link is in the description down below. Share this episode with a friend who desperately needs. You can reach out to me, Mike@survivingoutsides.com, or you can go to my LinkedIn page and DM me. Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

May 4, 2026Episode 38621 min

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

Send us Fan MailWe 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 wipes out 55% of revenue overnight • why “vibes” selling and blanket claims stop working • how buyers use AI to filter you before a meeting • using AI to create a business case and choose the right delivery channel • why buyers want to be led and taught something new • the P3 Sales Method as a timeless closing framework • follow-up, onboarding, and fulfillment as the start of the relationship • leveraging AI to support retention and reduce churn If you want to know more and you want to have a conversation about the specificity of your market and what you're trying to do, I offer a free consult, 30 minute 30-minute consult. You can reach out to me, Mike@SurvivingOutsideSales.com. You can reach out to me, DM me on LinkedIn. Or if you want to get started, you can go to go.p3salesmethod.com and you can grab the P3 sales method. Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

April 24, 2026Episode 38530 min

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

Send us Fan MailWe 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 in interviews when answers come from ChatGPT• the 3% rule and why most sales calls go sideways• building “off-ramps” to regain control when prospects get distracted• why top performers stay safe while passive reps get cut in the AI age• the reality that companies rarely provide deep sales training• why medical sales is crowded and being “replaceable” is a choice• the mindset trap of blaming the company and resisting coaching• the non-negotiable need to keep growing because there is no coasting in salesDM me on LinkedIn and just say, hey, I'd like to have a conversation. I do free consults If you want to get your hands on it, all you got to do is go to go.p3 salesmethod.com and you can sign up If you go to go.p3salesmethod.com and you purchase the p3 sales method and you send me a message on LinkedIn, I will do a 30-minute call with you and discuss your p3 sales method. Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

April 14, 2026Episode 38430 min

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

Send us Fan MailWe 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.• AI as an accelerator rather than a replacement for outside sales• Why skill development beats “education” and sales hacks• Knowing what questions to ask to frame the deal• Knowing what to listen for so you do not chase noise• Responding with confidence as the real separator• Using role play and repetition to sharpen performance• Preparing for “no” so objections do not throw you• How buyers judge tone, certainty, and business acumen• Why scripts break when real calls go off path• Rebuilding systems and the idea behind Sales Builder OS• What modern cold outreach gets wrong and why it gets deletedSend me a DM on LinkedIn and say, hey, I’d like to have a conversation. Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

March 27, 2026Episode 38332 min

AI Has Killed Outside Sales | SOS Ep. 383

Send us Fan MailWe break down how AI is reshaping outside sales and why the old linear sales process is collapsing under faster research and higher buyer skepticism. We share a practical way to use AI for speed without faking experience, plus the new “offer-first” reality that forces better prep, proof, and data. • why AI feels like a gold rush in sales right now • why AI tools cannot replace earned experience in live buying meetings • how ChatGPT can give confident but wrong answers and what that means for credibility • using multiple AI tools to cross-check insights and avoid bad inputs • the shift from linear selling to a value flow where buyers ask for the offer first • why discovery moves later and why pre-call planning matters more than ever • building proposals, ROI calculators, and real-world analytics instead of generic marketing material • why social proof, due diligence, and risk reversal now dominate the decision process • how fear of being wrong slows buying cycles and changes negotiation • why sales cycles are getting longer and why you must prospect more each year If you want to know how to harness the power of AI, then let me know. Reach out to me. You can click on one of the links below to schedule a consult, Mike, or you can email me Mike@survivingoutsales.com. But there's a sales scorecard that you can go to https://survivingoutsidesales.com/scorecard. That is survivingoutsidesales.com/scorecard. But if you want to have a conversation, I offer a free consult. It is the link is going to be in the bio. Let's have a conversation about where you are, where you've been, and where do you want to go in this new landscape of outside sales because it is a brave new world. Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

March 2, 2026Episode 38226 min

Brutal Truth about Outside Sales in 2026 | SOS Ep. 382

Send us Fan MailFeeling stuck between underpaid and overworked after years in outside sales? We dig into the quiet mistakes that stall careers—abandoning your network once you land a role, clinging to low-yield activity, and trusting trophies to speak for you—and lay out a practical path to get your leverage back. The big shift is treating your career like an operating system you can design, test, and scale.We start with the hard truth about timing and control: waiting until you’re unhappy or unemployed compresses options and pushes you into roles that don’t fit. With layoffs and market volatility, the only hedge is deliberate preparation. You’ll hear how top performers run concurrent plans—career, money, networking, and sales execution—so they can choose opportunities instead of chasing them. We also unpack why “President’s Club” rarely translates on its own and how to reposition your story around business acumen, territory turnarounds, and repeatable processes that win in resource-constrained environments.Then we get tactical. You’ll get a simple pipeline assignment to cut 20% of dead deals and reinvest that time in higher-value targets using a P3 lens: past, present, potential. We share practical ways to grow a real network on LinkedIn—thoughtful outreach, insight posts, and case-style updates—so you’re visible before you need visibility. We close by reframing your professional identity as a sales operator who adapts fast to changing buyer behavior, including the new realities AI is creating in how customers learn and decide.Want clarity on where you stand right now? Grab the free Sales Operator Diagnostic from the link in our bio, subscribe for more no-fluff career strategy, and leave a quick review to tell us which upgrade you’ll start this week. Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

January 9, 2026Episode 38118 min

Authority Beats Noise When Markets Go Soft | SOS Ep. 381

Send us Fan MailWe unpack why Q4 went soft across industries and how the first week of 2026 exposed a deeper shift in buyer behavior. We share routines, role-play tactics, and a clear plan to move from “rep” to trusted expert with simplicity and authority.• lean Q4 and the early 2026 surge• buyers flooded with info and more savvy• shift from rep to expert with clarity• routines for weekend and nightly practice• perfect practice to build confidence• role playing during drive time• simplicity and clarity as core edge• testing new platforms and handling churn• focusing on clients who value change• three ways to engage and get coachedJoin the community on Skool. It’s free to join. If you’re looking for coaching, sign up for one of the memberships. DM me on LinkedIn or email mike@survivingoutsidesales.com. Five stars, share it with a friend, and download any other episode.Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

December 29, 2025Episode 38021 min

Stop Waiting: Build A 2026 Sales Plan That Wins | SOS Ep. 380

Send us Fan MailWe challenge the myth of perfect timing and lay out a clear plan to build momentum, set aggressive goals, and win in a crowded market. We share how to plan at night, become a market expert, and turn systems and habits into a repeatable edge.• striking while the iron is hot• prioritizing primary tasks over busywork• planning nights and Sundays to own the week• building systems and processes for predictability• setting SMART goals and reverse engineering targets• navigating the holiday hangover and market timing• positioning as an expert to avoid price wars• networking with intent to open future doors• joining the SKOOL community for resources and coachingJoin us over at skool.com/survivingoutsidesales. You can sign up for free. Monthly webinars are free for the SKOOL community. If you want to take action and go to the next level, sign up for one of the membership levels.Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

December 23, 2025Episode 37931 min

From Info Overload to Clarity: How Outside Sales Reps Win In 2026 | SOS Ep. 379

Send us Fan MailWe break down why holding a signed deal for the next quarter backfires and how to build habits that weather quota changes. Then we share our pivot to a simpler community platform, a long-term coaching model, and a clarity-first framework that helps buyers decide.• striking while the iron is hot on late‑Q4 deals• the cost of waiting illustrated by pandemic losses• systems, processes, and habits over quota anxiety• information overload and buyer paralysis in 2025–2026• simplification and clarity as the new sales edge• shifting from vendor to long‑term consultant• building repeatable systems that protect pipeline• moving coaching to skool.com for community and ease• group coaching, VIP options, live calls, and replays• interview prep insights and ongoing training gaps• referral bonuses and early pricing for membersGo to skool.com/survivingoutsidesales to join the free community or upgrade for coaching. “Monday the 29th is going to be a webinar about how to set your goals for 2026" Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard

October 6, 2025Episode 37814 min

Sales Rep vs. Sales Pro | SOS Ep. 378

Send us Fan MailWe draw a hard line between a sales rep and a sales professional, and show how to run your territory like a business. Through real stories and simple systems, we map the habits that shrink dry spells, grow revenue, and put you in control of your career.• defining the rep vs professional mindset• treating your territory as a business• action bias over excuses and waiting• planning days, weeks, and months in advance• choosing focused weekend or evening work intentionally• service ethic and availability that earns trust• examples from coaching clients Erica and Brendan• preparing for layoffs and pivots with a live network• managing pipeline from unaware to advocate• reducing droughts with consistent prospectingSchedule a call and reach out to me on LinkedIn. Shoot me a DM.Support the showTo connect with the show: Subscribe, Download & Share!Would appreciate a 5-Star Rating if deserved on Spotify & Apple Podcasts!!!Connect with Mike:Mike@survivingoutsidesales.comLinkedIn: Mike O'Kelly | LinkedInCheck out your career path at:https://survivingoutsidesales.com______________________________________________________________________If you are looking for outside sales career clarity, go to:Surviving Outside Sales Scorecard