The Ray J. Green Show

Ray J. Green
  • 4.5 (11)
  • Management
  • Updated Biweekly

The Ray J. Green Show is for operators and founders who are already doing the work — but know that working harder isn't the same as getting it right. Each day, Ray J. Green — investor, operator, and founder of MSP Sales Partners — brings the sales tactics, leadership decisions, and strategic thinking he's learned from leading turnarounds, advising hundreds of B2B and MSP businesses, and making his share of costly calls. Some episodes are frameworks you can use tomorrow. Some are the thinking underneath the frameworks — the part nobody teaches. Most are both. From Cabo, where he lives with his family. No hype. Just what's working, what isn't, and how to think about the difference. Visit for fresh episode daily: https://podcast.rayjgreen.com

  1. 1d ago

    How One MSP Built Two Sales Champions From Scratch

    Elan Jones and Bradley Robinson are two of the best MSP salespeople in the country — and they work at the same company. Elan sold beer and cannabis before walking into IT sales the month the world locked down, then won MSP Salesperson of the Year. Bradley came from operations and project management, had never really sold, and became a two-time national Sales Champion finalist. Neither came from tech. This one's a first for the show: two sellers from the same shop, eCreek IT in Denver, breaking down a sales process repeatable enough to mint champions out of totally different people. We get into selling with confidence, why price objections are usually a value problem, how they keep a discovery call conversational without abandoning the checklist, the camaraderie of a two-person sales team, and where AI actually helps versus where it's just noise. If you're an MSP owner trying to build a sales engine that doesn't depend on you, this is the playbook. What You'll Learn • Why most price objections are really value problems from a weak discovery call • How to keep a discovery call conversational without abandoning the checklist • What it actually takes for an MSP owner to replace themselves in sales • Why drive beats credentials every time (and the camping story that proves it) • Where AI genuinely helps in sales — and where the human-first approach still wins Books & Resources Referenced • Myers-Briggs Type Indicator — Elan and Bradley both tested as ENTJ despite their different backgrounds. - https://www.myersbriggs.org/my-mbti-personality-type/mbti-basics/ • Calendly (referenced as "Calum"/scheduling tool) — automated meeting reminders and follow-ups. - https://calendly.com GEO (Generative Engine Optimization) — the emerging practice of optimizing to be recommended by AI search, discussed re: getting surfaced by ChatGPT for "IT providers in Denver."

    1h 21m

  2. Jun 15

    The "Whussification" of Sales Has to Stop — Art Sobczak

    Art Sobczak has been selling on the phone since he was 14 — starting with tickets to the Omaha police fundraising circus. Forty-plus years later: founder of Business By Phone, author of Smart Calling (three editions), host of The Art of Sales, 1,500+ trainings — including one for my first inside sales team at the US Chamber of Commerce twenty years ago. We get into what AI actually does for prospecting, why he'll never say "this is a cold call," the Salesperson's Oath, turning gatekeepers into allies, and the four pillars that separate salespeople who execute from those who collect training. If you or your team make outbound calls, this is the masterclass. What You'll Learn • Why AI is the greatest assistant — and worst replacement — salespeople have ever had • Why personalization without relevance is just spam • The Possible Value Proposition: the opener formula that replaces "this is a cold call" • Why permission-based openers trigger fight-or-flight in your prospect's brain • The Salesperson's Oath: first, create no resistance • The social engineering approach that turns gatekeepers into allies who prep your prospect before you call • "If the music is still playing, stay on the dance floor" — why rushing to book the meeting kills live conversations • The four pillars of top performers — and why identity beats discipline (Be-Do-Have, shades of Atomic Habits) • The backwards math: why 6-8 meetings a month might take 8 dream prospects and a handwritten note, not 14,000 dials ▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox ▸ Join My Newsletter for Weekly Sales Strategies: https://rayjgreen.beehiiv.com --------------------------- Books & Resources Referenced • Smart Calling: Eliminate the Fear, Failure, and Rejection from Cold Calling (3rd Edition) by Art Sobczak - https://www.amazon.com/Smart-Calling-Eliminate-Failure-Rejection/dp/111967672X • How to Get a Meeting with Anyone by Stu Heinecke - https://www.amazon.com/s?k=how+to+get+a+meeting+with+anyone+stu+heinecke • Get the Meeting!: An Illustrative Contact Marketing Playbook by Stu Heinecke - https://www.amazon.com/Get-Meeting-Illustrative-Marketing-Playbook/dp/1948836440 • Atomic Habits by James Clear - https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299 • Art's First 20 Seconds Formula masterclass — smartcalling.com • The Smart Calling Report newsletter — via smartcalling.com • The Art of Sales podcast — theartofsales.com • Dale Dupree Podcast Episode - https://www.youtube.com/watch?v=DotK-CSfWOI • Chris Walker Podcast Episode - https://www.youtube.com/watch?v=2o5mLPdJp2E

    1h 15m

  3. Jun 8

    Why AI Giants Are Hiring Human SDRs

    ▸ Slides + every prompt from this talk (free): mspsalestoolbox.com ▸ Work with us: mspsalespartners.com AI has changed how companies prospect, research, and communicate, but many of the world's largest technology companies continue investing heavily in human sales teams. This episode explores what AI can automate, what it still struggles to do, and why trust, judgment, and complex buying decisions continue to require skilled people. What You’ll Learn in This EpisodeWhy automation hasn't eliminated the need for human sales conversationsWhich parts of the sales process AI handles well—and which parts it doesn'tWhat the hiring decisions of major technology companies suggest about the future of sales // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses. → Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com → Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind. → Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com // Follow Ray on: YouTube | LinkedIn | Facebook | Twitter | Instagram

    54 min

  4. Jun 3

    The 5-Step Process Behind a Repeatable 68% Close Rate

    A high close rate is rarely the result of charisma or talent alone. When Ray reviewed the top finalists for MSP Salesperson of the Year, a clear pattern emerged: the best performers were all running nearly the same sales process. This episode breaks down the exact five-step framework behind close rates that are 68% — a the lowest rate — and why consistency in process matters more than most sales teams realize. What You’ll Learn in This EpisodeThe qualification mistake that causes many MSPs to leave deals on the tableWhy strong discovery creates higher close rates later in the processThe structure top performers use instead of overwhelming prospects with proposals and quotes // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses. → Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com → Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind. → Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com // Follow Ray on: YouTube | LinkedIn | Facebook | Twitter | Instagram

    12 min

  5. Jun 2

    How Different Would Your Life Be With an Empty Should List?

    A lot of people feel stuck because they think they need more information, another strategy, or outside guidance. But often, the real problem is execution avoidance. This episode explores the growing gap between the things we know we should do and the things we actually complete — and how that gap quietly impacts business growth, health, relationships, and momentum. What You’ll Learn in This EpisodeWhy most people already know the decisions that would improve their livesThe hidden psychological cost of carrying an unfinished “should list”How scheduling difficult tasks shifts the brain into execution mode // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses. → Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com → Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind. → Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com // Follow Ray on: YouTube | LinkedIn | Facebook | Twitter | Instagram

    8 min

  6. Jun 1

    Hard Things Piling Up Means Good Things Are Coming

    When difficult decisions start showing up everywhere at once — business, marriage, parenting, finances, health — it’s easy to assume life is breaking down. But often, those seasons are actually periods of transition and recalibration. In this episode, Ray explains why hard conversations and uncomfortable decisions are usually the entry point to meaningful progress, and how avoidance quietly creates long-term dissatisfaction. What You’ll Learn in This EpisodeWhy periods of intense pressure often happen right before major growthThe hidden long-term cost of avoiding uncomfortable decisionsHow to reframe difficult seasons as leverage points instead of warning signs // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses. → Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com → Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind. → Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com // Follow Ray on: YouTube | LinkedIn | Facebook | Twitter | Instagram

    8 min

  7. May 29

    What I Told 100 MSPs About Prospects Who Don't Buy

    A high close rate is rarely the result of charisma or talent alone. When Ray reviewed the top finalists for MSP Salesperson of the Year, a clear pattern emerged: the best performers were all running nearly the same sales process. This episode breaks down the exact five-step framework behind close rates as high as 76% — and why consistency in process matters more than most sales teams realize. What You’ll Learn in This EpisodeThe qualification mistake that causes many MSPs to leave deals on the tableWhy strong discovery creates higher close rates later in the processThe structure top performers use instead of overwhelming prospects with proposals and quotes // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses. → Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com → Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind. → Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com // Follow Ray on: YouTube | LinkedIn | Facebook | Twitter | Instagram

    7 min

  8. May 18

    He Outsold His Entire Team. His Boss Wrote Him Up. — Dale Dupree

    Dale Dupree sold copiers for 13 years and outsold his industry average by 11x — using a crumpled piece of paper instead of a thousand cold calls. After losing his father to cancer, he founded The Sales Rebellion. We got into why he thinks AI is making sales worse, how 20 letters outperformed a 4-person SDR team, why he'd hire a grocery bagger over a polished resume, and what servant leadership looks like when nobody's watching. What You'll Learn Why a crumpled letter consistently outperforms thousands of cold emailsHow an Australian SDR booked 12 meetings with 20 letters — and got written up for itThe one interview question Dale uses to identify coachable hiresWhy the SDR model fundamentally breaks relationship-first sellingWhat Dale's father taught him about leadership at 5 AM without knowing anyone was watching Resources thesalesrebellion.comDale on LinkedIn: linkedin.com/in/copierwarrior // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. About Ray: → Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more. → Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses. → Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com → Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind. → Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com // Follow Ray on: YouTube | LinkedIn | Facebook | Twitter | Instagram

    1h 6m
See All (291)

Trailer

4.5
out of 5
11 Ratings

About

The Ray J. Green Show is for operators and founders who are already doing the work — but know that working harder isn't the same as getting it right. Each day, Ray J. Green — investor, operator, and founder of MSP Sales Partners — brings the sales tactics, leadership decisions, and strategic thinking he's learned from leading turnarounds, advising hundreds of B2B and MSP businesses, and making his share of costly calls. Some episodes are frameworks you can use tomorrow. Some are the thinking underneath the frameworks — the part nobody teaches. Most are both. From Cabo, where he lives with his family. No hype. Just what's working, what isn't, and how to think about the difference. Visit for fresh episode daily: https://podcast.rayjgreen.com

Information

  • Creator
    Ray J. Green
  • Years Active
    2020 - 2026
  • Episodes
    291
  • Rating
    Explicit
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    The Ray J. Green Show