• Why I Shut Down My Commission Only Sales Team (A MSP Hiring Warning)
    Aug 15 2025

    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:

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    12 mins
  • This Is Why Your MSP Isn’t Growing
    Aug 8 2025

    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

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    14 mins
  • Autistic Introvert Who Outsold Everyone
    Aug 1 2025

    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

    Show More Show Less
    12 mins
  • How I Rescued A Hijacked MSP Sales Process
    Jul 25 2025

    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

    Show More Show Less
    19 mins
  • How to Apply the RIGHT Amount of Sales Pressure (Without Being Pushy)
    Jul 18 2025

    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


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    12 mins
  • Not Good at Sales? Neither Was I (MSP Game-Changer)
    Jul 11 2025

    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

    Show More Show Less
    14 mins
  • Treat Your SDRs Like Closers
    Jul 4 2025

    I break down why SDRs aren't just booking appointments—they're actually closing deals every single day, and how treating prospecting like a real sale will dramatically increase your appointment-setting success.

    Learn the exact framework I use to help MSP SDRs understand what they're really selling and why most people get this completely wrong

    //

    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

    Show More Show Less
    17 mins
  • The #1 Cause Of Slow Business Death (You’re Missing It)
    Jun 27 2025

    I share a real conversation I had with an MSP business owner who was avoiding making tough decisions about an underperforming salesperson, and explain why true leadership means making difficult decisions that others may disagree with rather than letting problems persist to keep everyone happy.

    //

    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

    Show More Show Less
    10 mins