The Prepared Seller

Paul M. Caffrey
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Want to be a top performing seller in 2025? You're in the right place. The #1 Sales Podcast for Ambitious Account Executives and Founder Sellers looking to prospect better and sell more. Dive deep into the sales world with the unparalleled expertise of Paul M. Caffrey, acclaimed author of "The Work Before the Work: The Hidden Habits Elite Sales Professionals Use to Outperform the Competition." This is not just another sales podcast; it's your exclusive gateway to upscaling your sales prowess, honing unmatched prospecting skills, and accelerating your journey to the top of the sales ladder. Each episode serves as a goldmine of actionable insights and proven frameworks, meticulously designed for the forward-thinking Account Executive. Whether it's Paul deconstructing the intricacies of a pivotal sales strategy or engaging in enriching conversations with industry titans, founders, and the crème de la crème of sales professionals, every minute promises a transformative experience. If you're an Account Executive with a burning ambition to be extraordinary, this podcast isn't just recommended—it's essential. Join us and redefine your sales narrative!

  1. 10/28/2025

    You Don’t Have a Pipeline Problem, You Have a Momentum Problem | Ep 64

    👤 Connect with Paul 💼 LinkedIn: https://www.linkedin.com/in/paulcaffrey/  🎤 Planning your sales kickoff? Click here.  🔗 Quick Summary Most salespeople think their deals stall because of ghosting or a weak pipeline — but that’s not the real issue. In this solo episode, Paul Caffrey reveals the hidden reason deals slow down: lost momentum. You’ll learn how to regain control of your deals, keep energy high between meetings, and move faster in Q4 using four simple, practical steps that top-performing sellers use every day. 🕒 Timestamps 00:00 — “They didn’t have a ghosting problem. They didn’t have a pipeline problem. They had a momentum problem.” 01:10 — Why ghosting isn’t the issue — it’s your deal velocity 02:30 — Tip #1: Prepared next steps — decide what, who, when, and why before every call 04:45 — Tip #2: Not all pain leads to action — how to spot the difference 06:10 — “Every problem does not mean action” — how to test real urgency 07:25 — Tip #3: Book a meeting from a meeting — the habit elite sellers swear by 09:15 — How to uncover hidden objections when prospects delay booking 10:40 — Tip #4: Follow up individually — know who’s pro, neutral, or against your deal 12:00 — Why calling stakeholders post-meeting gives you a 10x advantage 13:00 — Recap: The four momentum builders to speed up your Q4 pipeline 💡 Key Takeaways ⚡ You don’t have a pipeline problem. You have a momentum problem. 🧭 Prepared sellers control pace. Always define the next step — what, who, when, and why. 💬 Pain ≠ urgency. Not every frustration deserves a fix. 📅 Never end a meeting without the next one scheduled. 👥 Call stakeholders individually before and after meetings to test alignment. 🚀 Momentum is built, not chased. Prepared sellers move faster because they plan faster. 🧩 The Four Momentum Builders Have prepared next steps before every meeting. Validate pain — confirm it’s a real problem, not a mild inconvenience. Book a meeting from a meeting. Follow up individually to gauge stakeholder support. 🎧 Episode Quote “They didn’t have a ghosting problem. They didn’t have a pipeline problem. They had a momentum problem.” 🎯 Call to Action Before your next meeting, write down: ‘What’s the decision I expect to be made today?’ If you can’t answer that, neither can your client. (c) Paul M. Caffrey — Speaker | Author | Sales Coach LinkedIn  | Book Paul for Your Sales Kickoff

    8 min

  2. 10/25/2025

    Discovery Calls Must Die w/Lee Salz | Ep 63

    👤 Connect with Paul 💼 LinkedIn: https://www.linkedin.com/in/paulcaffrey/ 🎤 Planning your sales kickoff? Click here. 👤 Connect with Lee 🌐 Website: https://salesarchitects.com 📘 Book hub: https://firstmeetingbook.com 🔗 Quick Links (mentioned in the episode) 📘 Free chapter + bonuses for The First Meeting Differentiator: https://firstmeetingbook.com 🧠 Tip sheet — “Providing Meaningful Value in First Meetings”: https://meaningfulvalue.com 🏗️ Lee’s site (Sales Architects): https://salesarchitects.com 📚 Book recommendations: Selling from the Heart (Larry Levine), A Mind for Sales (Mark Hunter)   Episode Summary Sales legend and proud contrarian Lee Salz joins Paul to dismantle sacred cows in sales: why traditional discovery meetings must die, why ICP is a lottery ticket (and TCP is what you actually need), and why pain ≠ problem—and how to tell the difference fast. You’ll learn how to win more first meetings by delivering meaningful value, how to bake that into your prospecting, the “unknowingly” strategy that sparks curiosity on cold outreach, and one simple habit that eliminates ghosting.   Timestamps 00:08 — Cold open: “What if everything you’ve been taught about sales is wrong?” 02:09 — Meet Lee Salz & the “sales contrarian” stance 03:07 — Why “sales is a numbers game” is terrible counsel 04:10 — Stop living by “you’re only as good as your last sale” → it’s about your next sale 05:46 — Why discovery meetings need to die (free chapter at firstmeetingbook.com) 06:45 — Discovery vs. consultation: what the buyer should actually get from the first meeting 07:35 — TP vs. bidet analogy: takeaway sales vs. demand-gen sales 09:51 — Define “meaningful value” and use it in your outreach (meaningfulvalue.com) 11:18 — Use meaningful value to secure the first meeting 14:34 — ICP is out, TCP is in: a 12-component Target Client Profile that actually qualifies 17:44 — Qualify early and often (including first 15 minutes of the first call) 19:47 — You’re not obligated to demo or meet again 21:19 — Never “send the proposal” — present it live 23:51 — Pain vs. Problem (P-A-IN): inconvenience vs. action-worthy issues 29:21 — #1 prospecting tip: the “unknowingly” strategy that triggers curiosity 32:53 — #1 anti-ghosting tip: book the next meeting before you hang up 34:50 — Promotion advice: it’s a job change, not “more of sales” 36:53 — Book recs: Selling from the Heart & A Mind for Sales 37:52 — “The work before the work”: prep with modern tools (yes, AI) 38:29 — Where to find Lee + bonus masterclasses for book buyers   Key Takeaways 💀 Discovery is dead. Consultation wins. Your first meeting must deliver meaningful value to the buyer, not just extract info for you. ✉️ Bake value into your outreach. Tease the meaningful value in your invite (“When we meet, I’ll share…”). 🎯 ICP → TCP. Replace “ideal” (imaginary) with a Target Client Profile—who perceives the most value and is most likely to close. ⚡ Pain isn’t enough. Use P-A-IN: Problem, Action, Inconvenience, Neutral. 🚫 Qualify early, say no more. Decide go/no-go in the first meeting. 👻 Kill ghosting. Schedule the next step in the meeting. 🔍 Curiosity converts. Try the “unknowingly” strategy (“You’re unknowingly overpaying for…”).   Resources Mentioned The First Meeting Differentiator — Free Chapter & Masterclasses Tip Sheet: Meaningful Value in First Meetings Sales Architects — Lee’s Website Selling from the Heart — Larry Levine A Mind for Sales — Mark Hunter   🎯 Call to Action If you run first meetings, replace discovery with consultation this week: define one meaningful insight or best practice your prospects would thank you for—then share it in your next call. Your pipeline (and your reputation) will thank you.

    36 min

  3. 10/11/2025

    Brands that lead the future won't say LOOK AT ME.They'll say COME WITH ME w/Claire Dowdall | EP 62

    Connect with Claire Dowdall here.  Summary In this episode of the Prepared Seller podcast, Paul M. Caffrey interviews Claire Dowdall, a brand strategist and speaker, who shares insights on brand strategy, the importance of capturing real-time feedback, and the power of storytelling in personal branding. Claire emphasizes the need for effective communication skills in leadership and sales, and discusses the findings from the Conversational Edge study, highlighting the crisis of poor communication in the workplace. She also provides practical tips for sales professionals, including the importance of preparation and staying curious during conversations.   Takeaways Put yourself in the position of the person having the experience. Switch testimonials into impact stories to measure brand impact. Capture feedback while emotions are still fresh. Focus on conversations to gain insights into customer experiences. Use the 'Come With Me' approach to share stories. Set big goals to filter out distractions and focus on what matters. Effective communication is crucial for leadership and promotions. Women often feel less confident in conversations than men. Communicating your value is key to career advancement. Outsource lower-value tasks to focus on higher-impact work.

    43 min

  4. 08/16/2025

    3 biggest mistakes I’ve seen after 291 one-on-one sales coaching sessions | Ep 61

    Assess Yourself or your sales team vs Top Performers Here for FREE! or  Free Sales Preparation Course to help you outperform the competition in 19 minutes. After delivering 291 one-on-one sales coaching sessions in just six months, Paul M. Caffrey has seen the same three mistakes holding salespeople back again and again. In this episode, Paul breaks down each mistake, why it matters, and the exact steps to fix it — so you can improve your forecasting, increase your close rate, and sell with more confidence. Whether you’re an Account Executive, a Sales Leader, or preparing for your next SKO, these three fixes will help you move deals faster and close more business.   Timestamps 00:00 – Intro: 291 coaching sessions in six months 00:18 – Podcast credits 00:33 – Why you’re losing deals (and it’s not what you think) 01:15 – About Paul M. Caffrey and The Work Before the Work 02:05 – Mistake #1: Skipping Mutual Success Plans 03:20 – How to make Mutual Success Plans a habit 04:02 – Mistake #2: Not Confirming the Agenda 05:05 – How to make agenda confirmation a habit 05:40 – Mistake #3: Avoiding Video Prospecting 06:42 – How to make video prospecting a habit 07:30 – Closing thoughts: Fix one, fix all three

    9 min

  5. 08/03/2025

    6 Places Top Sellers Use Video to Win More Deals | Ep 60

    Assess Yourself or your sales team vs Top Performers Here for FREE! or  Free Sales Preparation Course to help you outperform the competition in 19 minutes. All salespeople send emails. Some send videos. But top performers? They send video at six key moments in their sales process—and it’s changing the game. In this episode, Paul breaks down what he learned from Shari Levitin (one of the world’s leading sales trainers) about how elite sellers are using video to build trust, increase open rates, and close more deals—without needing a big following or fancy tech. You’ll learn: Why video builds trust faster than text The 6 best points to send sales videos (with examples) How to structure short, powerful messages that get results If you’re in B2B and want to cut through the noise—this is your playbook.

    7 min

  6. 07/25/2025

    AEs don't need to prospect w/ Datarails CRO Aviv Canaani | Ep 59

    Connect with Datarails CRO Aviv Canaani on LinkedIn THE PREPARED SELLING COURSE | A free 29-minute course that shows Account Executives how top performers prepare for demos, discovery, and referrals — and win more deals, faster. GET FREE ACCESS The Elite Sales Professional Assessment: Answer 15 Questions to Benchmark your ability to sell vs elite sales professionals. GET YOUR SALES BENCHMARK HERE Summary In this conversation, Aviv Canaani, the CRO of DataRails, shares insights on building a successful go-to-market strategy focused on driving inbound leads, optimizing sales processes, and fostering a high-performing sales team. He emphasizes the importance of metrics, conversion rates, and a structured sales methodology to ensure predictable revenue. Aviv also discusses the significance of team motivation, effective hiring practices, and the role of preparation in achieving sales success. Takeaways Creating a go-to-market machine is essential for driving inbound leads. Metrics like meeting to close one are crucial for evaluating sales performance. A structured sales methodology helps in scaling the sales process effectively. Speed to lead is critical in converting prospects into customers. Trust and collaboration within the sales team enhance overall performance. Promoting from within and recognizing top performers fosters a motivated sales team. Evaluating sales talent through simulations can reveal true capabilities. Forecasting sales requires a mix of historical data and current pipeline insights. Preparation for sales calls is vital for success and should be prioritized. CROs must focus on building a predictable revenue model to satisfy stakeholders.

    46 min

  7. 02/22/2025

    Top 5 Sales Tips w/#1 Sales Nav Expert Perry van Beek | Ep 058

    "Don't be afraid to give out your knowledge, to share your knowledge freely." Perry van Beek (Connect on LinkedIn) Want to prepare your sales team to become top performers in 2025? Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Ambitious Account Executives: Coaching with Paul FULL: Join Waitlist  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn. Episode Overview:In this episode, Paul M. Caffrey sits down with Perry Van Beek – best-selling author of LinkedIn Sales Navigator for Dummies, with 30 years of sales expertise and over 150 LinkedIn recommendations. Perry dives into his top tips for prospecting, sales, and using LinkedIn Sales Navigator to transform your approach. Learn how helping people, going the extra mile, and setting healthy boundaries can turn prospects into long-term clients. Key Discussion Points: Prospecting Through Value:Perry explains how shifting from sending generic pitches to offering free advice on LinkedIn helped him secure his first clients. His approach is simple – share your knowledge freely and help potential customers before asking for business. Sales Strategy – The Extra Mile:Discover why Perry believes that going that extra mile not only deepens client relationships but often eliminates the need for traditional prospecting. As he puts it, “You will never ever have to prospect again” when you consistently add value. Promotion & Boundaries:Learn the importance of saying “no” and setting boundaries. Perry shares how learning to prioritize and even decline certain tasks can be key to avoiding burnout and even earning a promotion. Recommended Reading for Sales Success:Perry cites the inspiration behind his journey – including Screw It, Let's Do It by Richard Branson and The One Thing by Greg McKeown – as essential reads for anyone looking to elevate their sales game. Optimizing Your LinkedIn Presence:From refining your LinkedIn profile to clearly defining your ideal client profile, Perry underscores why a customer-centric approach is critical for leveraging Sales Navigator effectively. Connecting with Perry:Find Perry on LinkedIn (linkedin.com/in/perryvanbeek) and take advantage of his free 10-minute consultation call to fine-tune your Sales Navigator strategy. Episode Chapters & Timestamps: 00:00 – Introduction & Perry’s Sales JourneyMeet Perry Van Beek and learn about his extensive sales background. 02:40 – Going the Extra MilePerry reveals how contributing to the buying journey can transform your prospecting efforts. 04:33 – The Power of Saying “No”Discover why setting boundaries is crucial for success and sustainable growth. 06:38 – Must-Read Sales BooksPerry discusses the inspirational books that influenced his career. 09:22 – Crafting a Customer-Centric LinkedIn ProfileTips on making your profile resonate with potential clients. 09:31 – Mastering Sales NavigatorPractical strategies to leverage this essential tool for better sales outcomes. 13:04 – How to Connect & Get StartedLearn how to book a free consultation with Perry and access his wealth of free resources. Call-to-Action: Connect with Perry: Visit his LinkedIn profile at linkedin.com/in/perryvanbeek. Book a Free Consultation: Check the top link in the show notes to schedule your 10-minute call and kickstart your Sales Navigator strategy. Subscribe & Share: Don’t miss out on more actionable sales tips—subscribe and share this episode with your network.

    14 min

  8. 02/14/2025

    Top 5 Sales Tips w/POINTER Founder Ricky Pearl | Ep 057

    "Sell to people who want your product, not who need your product." Pointer Founder Ricky Pearl Prepare yourself & your sales team to become top sales performers in 2025. Event Organisers: Paul M. Caffrey | Sales Keynote Speaker:  Check Paul's availability to speak at your event. Ambitious Account Executives: Coaching with Paul: Apply Here Founder Sellers: Prepared Selling OS for AI Founders: Learn how to build your first sales team here.  Get the Book: "The Work before the Work, The Hidden Habits Elite Sales Professionals Use to Outperform the Competition" here or listen free on Spotify premium Connect with Paul M. Caffrey on LinkedIn. Connect with Ricky Pearl on LinkedIn or check out his company POINTER here.   Summary In this conversation, Ricky Pearl shares his top sales tips and insights. The main themes include prospecting, selling to people who want your product, getting promoted, recommended books, and preparation. Ricky emphasizes the importance of consistency in prospecting and having conversations with potential buyers. He also highlights the value of selling to people who genuinely want your product, rather than those who simply need it. To get promoted, Ricky advises focusing on professional development and understanding your manager's job. He recommends books that promote introspection and understanding human nature. In terms of preparation, Ricky suggests knowing what the prospect expects you to know without over-preparing. Takeaways Consistency is key in prospecting and having conversations with potential buyers. Sell to people who genuinely want your product, not just those who need it. Focus on professional development and understand your manager's job to get promoted. Recommended books for sales include those that promote introspection and understanding human nature. Preparation should involve knowing what the prospect expects you to know without over-preparing.

    5 min
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About

Want to be a top performing seller in 2025? You're in the right place. The #1 Sales Podcast for Ambitious Account Executives and Founder Sellers looking to prospect better and sell more. Dive deep into the sales world with the unparalleled expertise of Paul M. Caffrey, acclaimed author of "The Work Before the Work: The Hidden Habits Elite Sales Professionals Use to Outperform the Competition." This is not just another sales podcast; it's your exclusive gateway to upscaling your sales prowess, honing unmatched prospecting skills, and accelerating your journey to the top of the sales ladder. Each episode serves as a goldmine of actionable insights and proven frameworks, meticulously designed for the forward-thinking Account Executive. Whether it's Paul deconstructing the intricacies of a pivotal sales strategy or engaging in enriching conversations with industry titans, founders, and the crème de la crème of sales professionals, every minute promises a transformative experience. If you're an Account Executive with a burning ambition to be extraordinary, this podcast isn't just recommended—it's essential. Join us and redefine your sales narrative!

Information

  • Creator
    Paul M. Caffrey
  • Years Active
    2023 - 2025
  • Episodes
    67
  • Rating
    Clean
  • Show Website
    The Prepared Seller