Repeatable Revenue

Ray J. Green
  • 4.5 (11)
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  • UPDATED BIWEEKLY

A podcast for MSPs and B2B business owners who want to scale sales. Repeatable Revenue is hosted by Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family. This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.

  1. 2D AGO

    MSP Owners: Stop Getting Stuck in Limbo (Here’s 3 ways to force decisions)

    I recently coached an MSP seller who spent over 20 hours chasing a $5,000 deal only to get completely ghosted at the end - sound familiar? If you're tired of getting stuck in sales purgatory, chasing deals you were never going to win, I'm going to show you three specific strategies to break free and force more decisions. First, use your discovery phase strategically to understand their actual buying process by asking the right questions about urgency, decision-making structure, and stakeholders involved. Second, after your proposal presentation, get them to quantify their interest on a 1-10 scale and then ask the crucial follow-up question: "What would make it a 10?" This reveals the real objections you need to address. Finally, make it easy for prospects to say no by giving them permission to tell you if they've gone a different direction - you'll either stop wasting time on lost deals or they'll put themselves back into the buying process. These three techniques will help you allocate your time more effectively and stop chasing deals that are already dead. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

  2. AUG 22

    The Dumbest Sales Advice I've Seen This Week (For MSPs)

    I see ads all the time claiming that "building rapport" is a lie and you need to learn how to sell without it - but these so-called experts are completely missing the point. In this video, I break down the massive misunderstanding around what rapport actually is in sales. It's not about small talk, weather conversations, or chatting about family photos on someone's desk - that's just likability, not rapport. Real rapport is about establishing trust, credibility, and demonstrating that you have the expertise to solve their problems. I'll show you how to build genuine rapport by showing up prepared, asking targeted questions that prove you understand their business and industry, and positioning yourself as a credible expert who can actually deliver results. If you're in MSP sales and tired of the surface-level rapport advice, this video will set the record straight on what rapport really means and how to build it the right way. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

    2 min

  3. AUG 15

    Why I Shut Down My Commission Only Sales Team (A MSP Hiring Warning)

    I inherited a commission-only sales team at the US Chamber of Commerce and had to shut down the entire division 18 months later. In this video, I'm sharing why commission-only structures actually sabotage sales teams and can ruin your business culture. Most business owners think commission-only means hungrier, more driven reps, but that's not necessarily true. I'll break down the two major problems I've experienced with commission-only structures: how they drive away top talent who see them as red flags, and how they attract mercenaries who only care about one thing - their commission. If you're an MSP owner considering your sales compensation strategy, this is a cautionary tale you need to hear. I'll show you why sharing the risk with your sales team through a base salary plus commission structure will help you attract professionals who want to be part of your team and contribute to a strong sales culture. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

  4. AUG 8

    This Is Why Your MSP Isn’t Growing

    I was on a flight with my family when we had an emergency landing, and watching how the first responders handled the situation taught me the most important lesson about running a business: successful CEOs don't try to solve every problem at once, they identify the single most critical priority and focus all their resources on that one thing // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

    14 min

  5. AUG 1

    Autistic Introvert Who Outsold Everyone

    I bombed my first sales interview but still got hired, and that experience taught me the three key traits I now look for when hiring salespeople that matter more than experience or charisma. Despite being introverted with no sales background, I went on to become a top performer and help raise over $100 million - here's what really matters in sales hiring. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

  6. JUL 25

    How I Rescued A Hijacked MSP Sales Process

    This episode breaks down how an MSP sales professional successfully salvaged a deal after losing control of the discovery process when a third-party consultant flipped the script and interviewed him instead of allowing him to ask questions. Ray shares three key insights extracted from analyzing the meeting transcript and demonstrates how to use strategic questioning and positioning to regain control during the proposal stage. Despite starting as one of ten candidates in a compromised position, the systematic approach helped the salesperson become a finalist and ultimately win the sizable deal. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

    19 min

  7. JUL 18

    How to Apply the RIGHT Amount of Sales Pressure (Without Being Pushy)

    Ray breaks down a real coaching scenario where an MSP salesperson lost a deal to an inferior provider despite proving compliance issues and security vulnerabilities. The prospect chose to give their current provider "one more chance" instead of switching to better service. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

  8. JUL 11

    Not Good at Sales? Neither Was I (MSP Game-Changer)

    Shy, introverted, and autistic - I bombed my first sales interview selling knockoff perfume. But I went on to never miss a sales target for 3 consecutive years and built a 20-year career helping MSPs scale from $5M to $50M+. If you're a technical founder who thinks you're "not cut out for sales," this video will change everything. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. 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

    14 min
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4.5
out of 5
11 Ratings

About

A podcast for MSPs and B2B business owners who want to scale sales. Repeatable Revenue is hosted by Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family. This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.

Information

  • Creator
    Ray J. Green
  • Years Active
    2020 - 2025
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    Repeatable Revenue