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. 5D AGO

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

    Send us a text 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    21 min

  2. 12/23/2025

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

    Send us a text 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    30 min

  3. 10/06/2025

    Sales Rep vs. Sales Pro | SOS Ep. 378

    Send us a text 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    13 min

  4. 10/01/2025

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

    Send us a text 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    26 min

  5. 09/09/2025

    3 Keys to Greatness in Sales | SOS Ep. 376

    Send us a text 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    27 min

  6. 08/30/2025

    The Three Keys That Unlock Every Door in Sales | SOS EP. 375

    Send us a text The know, like, and trust framework is the essential foundation for both landing a sales job and closing deals with prospects. Mike O'Kelly breaks down the specific mechanics behind each component and provides actionable strategies for implementing them effectively. • Your resume is a passive introduction that forms the first impression when you're not present • Hiring managers filter candidates based on whether they know, like, and then trust them • Follow-up demonstrates trustworthiness and consistency in both job hunting and sales • Buyers care more about what happens when things go wrong than when they go right • The rule of three applies universally across sales processes: planning, building, and launching • Being responsive shows employers you can handle the responsibilities of the role • The same three-phase framework applies whether you're getting into sales, dominating, or moving on If you want to chat about your situation or get a territory audit with a free strategy session, click the link in the show notes. I do two to three sessions per week with listeners, helping sales professionals meet their goals and survive outside sales. 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    14 min

  7. 08/26/2025

    Focus on closing the deal, not squeezing every dollar | SOS Ep. 374

    Send us a text Mike shares valuable sales lessons from three car-buying experiences where salespeople refused to negotiate, costing them sales when he took his business elsewhere. • Being unwilling to negotiate with a ready buyer is a major sales mistake • Three different car dealerships lost Mike's business by refusing reasonable offers • Each dealership called back when it was too late, after he'd bought elsewhere • Focus on closing the deal rather than squeezing every dollar from each transaction • Getting a deal done and moving to the next prospect is more important than maximizing commission • If you can't meet a customer's exact price, find creative ways to add value • Never let a ready buyer walk away—the opportunity cost is too high • When someone shows buying signals, do whatever you can to accommodate the sale Mike is giving away three months of one-on-one coaching and three months of Sales Builder Accelerator. Email mike@survivingoutsidesales.com or connect on LinkedIn to enter through the end of September. 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    29 min

  8. 07/22/2025

    Mastering Buyer Psychology: Do's and Don'ts for Securing Meetings | SOS Ep. 373

    Send us a text Ever wonder why your meeting requests keep getting ignored? In this eye-opening episode, I pull back the curtain on what really happens when you pitch a potential buyer and why most approaches fail miserably. Drawing on my experience of receiving 10-12 pitches daily, I break down the psychology behind why the same boring templates and self-centered approaches get immediately dismissed. The truth is startling but simple: nobody cares that you're trying to hit your quota. Decision-makers calculate their time's worth in hundreds of dollars per hour and are naturally skeptical after past disappointments. When you ask for a "quick 15-minute call," they're mentally translating that to 30+ minutes and asking, "Is this worth $200+ of my time?" Without establishing credibility and differentiating yourself first, the answer is almost always no. I share practical strategies for standing out from the crowd by flipping the traditional approach. Instead of asking for time upfront, start by depositing value—share insights, provide unexpected help, or demonstrate you've done your homework. Connect every meeting request to a specific, better outcome for the buyer. Ask questions that make them stop and think, disrupting their automatic filters. Most importantly, meet them on their terms, not yours. The modern sales landscape demands a consultant mindset rather than product-pushing. Focus entirely on the buyer's future state and how your solution creates meaningful improvement from their current situation. This investment-first approach not only increases your chances of securing meetings but builds the trust foundation necessary for successful, long-term relationships. Ready to transform your approach? DM me on LinkedIn or email mike@survivingoutsidesales.com for a free 30-minute consultation where we can discuss specific strategies tailored to your situation. 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 Click to join the Surviving Outside Sales community on SKOOL: Skool.com/survivingoutsidesales ______________________________________________________________________ If you are in outside sales and have had any of the following: - New to Outside Sales - New to an industry, new product, new territory - any type of change - Experienced, but have lacked training and business development - Seasoned but feel like you have hit your ceiling and need a reboot If any of those descriptions sound like you or someone you know, join the FREE Surviving Outside Sales Skool community skool.com/survivingoutsidesales

    27 min
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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 - 2025
  • Episodes
    380
  • Rating
    Explicit
  • Copyright
    © 2025 Surviving Outside Sales
  • Show Website
    Surviving Outside Sales

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