• The #1 Reason MSP Sales Reps Fail to Close (MSP Sales Training)
    Sep 26 2025

    I reveal the shocking truth about why most MSP deals actually fail - and it's not what you think. After listening to countless sales calls, I've discovered that deals don't die because of timing, price, or contract issues.

    They fail because sales reps never actually ask for the sale! I know it sounds crazy, but I'm going to prove exactly how this happens and show you the simple techniques I use to avoid getting ghosted by prospects.

    I'll walk you through my proven closing strategies, including the exact questions that force prospects to reveal their real objections so you can address them on the spot instead of hoping they'll magically say yes later. If you're tired of deals getting stuck in "we'll think about it" purgatory, this video will change how you close forever

    //

    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

    //

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    12 mins
  • The 3-Role Split That Grew This MSP 30%
    Sep 19 2025

    I analyze a case study of a $7 million MSP owner whose close rates were declining despite having good reps and processes. What I discovered during our audit was that they had one rep who was phenomenal at opening deals through LinkedIn prospecting and another who was excellent at closing, but both were trying to handle the entire sales cycle from lead generation to account management.

    //

    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
    13 mins
  • MSP Sales Training: The Secret to Never Leaving a Meeting Empty-Handed
    Sep 12 2025

    I share a crucial sales framework that can prevent you from losing deals after what seemed like successful presentation meetings. I explain the "BAMFAM" (Book a Meeting from a Meeting) strategy, which ensures you never leave a proposal meeting empty-handed without either a clear decision or a confirmed next step on the calendar.

    //

    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
    13 mins
  • The MSP Growth Strategy No One Talks About (Compounding Wins)
    Sep 5 2025

    I share how downloading a "Couch to 5K" app - despite being able to run half marathons - taught me a powerful lesson about achieving big goals in business.

    After hitting a mental block that kept sabotaging my runs, I discovered that starting embarrassingly easy and building small, consistent wins creates unstoppable momentum. This same principle of breaking down massive business goals into bite-sized, achievable steps helps you develop a winning habit that compounds over time, whether you're trying to scale from $1M to $10M or launch that outbound sales operation you've been putting off.

    //

    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
  • MSP Owners: Stop Getting Stuck in Limbo (Here’s 3 ways to force decisions)
    Aug 29 2025

    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

    Show More Show Less
    12 mins
  • The Dumbest Sales Advice I've Seen This Week (For MSPs)
    Aug 22 2025

    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

    Show More Show Less
    2 mins
  • 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:

    YouTube | LinkedIn | Facebook | Twitter | Instagram

    Show More Show Less
    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

    Show More Show Less
    14 mins