Surviving Outside Sales

Mike O'Kelly
  • 5.0 (13)
  • CAREERS
  • UPDATED SEMIWEEKLY

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! 

  1. MAR 27

    AI Has Killed Outside Sales | SOS Ep. 383

    Send us Fan Mail We 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 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

    30 min

  2. MAR 2

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

    Send us Fan Mail Feeling 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 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

    27 min

  3. JAN 9

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

    Send us Fan Mail We 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 coached Join 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 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

    19 min

  4. 12/29/2025

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

    Send us Fan Mail We 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 coaching Join 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 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

    21 min

  5. 12/23/2025

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

    Send us Fan Mail We 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 members Go 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 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

    32 min

  6. 10/06/2025

    Sales Rep vs. Sales Pro | SOS Ep. 378

    Send us Fan Mail We 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 prospecting Schedule a call and reach out to me on LinkedIn. Shoot me a DM. 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

    14 min

  7. 10/01/2025

    Closing Q4: Budgets, Urgency, and ROI Pull-Through | SOS Ep. 377

    Send us Fan Mail We break down a Q4 game plan that turns limited selling days and budget dynamics into a focused path to close. We show how to qualify for budget, reduce perceived risk, and become memorable so champions can sell your solution internally. • Q4 as execution: pull-through over prospecting • budget mechanics, Section 179, and spend-it-or-lose-it reality • reducing risk with ROI, timelines, and training plans • identifying decision makers and mapping approval chains • compressing calendars: 48 selling days and reverse planning • three levers: right buyer, time focus, structured pressure • shifting from noise to memorable, buyer-centered follow-up • grit check for outside sales and where coaching helps Book a free Q4 strategy session with Mike.  Email: Mike@SurvivingOutsides.com Connect on LinkedIn and say, “I need a Q4 strategy.” 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

    28 min

  8. 09/09/2025

    3 Keys to Greatness in Sales | SOS Ep. 376

    Send us Fan Mail Mike O'Kelly breaks down the three key elements that separate great sales professionals from the rest: taking massive action, continuously learning new skills, and building repeatable processes. • Taking massive action means going beyond basic activity to create productivity • Most sales happen between the 5th and 12th touch point, but many salespeople give up too soon • Prospects receive dozens of pitches daily, making persistence and quality outreach essential • Shift from demanding prospect time to providing valuable insights that move them from unaware to aware • Successful sales professionals position themselves as go-to experts in their field • Growth never happens in your comfort zone - constantly learn new skills and adapt to market changes • Building repeatable processes is crucial for scaling success and preventing the "spinning plates" syndrome • The P3 sales method creates a framework where buyers view you as a consultant, not just a vendor • Most sales failures stem from process breakdowns, not ability issues I do a free 30-minute consult if you want to learn more about where you are in your career and how to elevate your sales performance. Reach out to me at mike@survivingoutsidesales.com or connect with me on LinkedIn and shoot me a DM. The link will be in the show notes - book a time for a free 30-minute call to see where you are, where you're headed, and get a territory audit. 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

    29 min
See All (383)

Ratings & Reviews

5
out of 5
13 Ratings

About

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! 

Information

  • Creator
    Mike O'Kelly
  • Years Active
    2021 - 2026
  • Episodes
    383
  • Rating
    Explicit
  • Copyright
    © 2026 Surviving Outside Sales
  • Show Website
    Surviving Outside Sales

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