I burned through $50,000 and four virtual assistants trying to fix my operations and tech stack, and things only got worse. The problem? I was trying to skip the hard part - actually understanding what needed to be fixed before hiring someone to fix it.

Dan Sullivan's "Who Not How" advice is brilliant, but there's a critical piece missing that cost me nine months and left my business in worse shape than when I started. The real formula isn't just "who not how" - it's "you, then who, somehow."

I see MSP owners make this exact same mistake on the sales side constantly. They hire agency after agency, SDR after SDR, trying to outsource their way out of a problem they don't fully understand. If you've burned through multiple people in the same role, the role is probably wrong - not the people.

You don't need to become an expert, but you need to understand the problem well enough to know who you're hiring for, what success looks like, and how to measure progress. Otherwise, you're just throwing money at a problem and hoping it goes away.

This was an expensive lesson for me. Hopefully you can learn it without paying the same tuition

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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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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

I used to think "Always Be Closing" was outdated, sleazy sales advice, but I've completely changed my mind. In this video, I break down why ABC is actually the foundation of consultative selling for MSSPs and B2B sales.

The truth is, every single step in your sales process—from discovery calls to assessments to proposals—should be designed with one goal: moving the deal forward and closing the sale. I'll show you the simple framework I use to redesign sales processes, explain why most salespeople are treating discovery and assessments like information gathering instead of closing opportunities, and reveal the biggest mistake I see during proposals that kills deals.

If you're in MSP sales or any B2B selling, this reframe will change how you approach every interaction with prospects.

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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

Discover why most MSP deals are actually won or lost during the discovery phase, not at the close! In this video, I break down how to engineer your discovery process to address objections before they even come up.

I'll show you how to plant the seeds early by asking strategic questions that uncover pain points, buying motivations, urgency levels, and decision-making processes - then use their own words as your most powerful rebuttals later. Instead of scrambling to overcome predictable objections like "it's too expensive" or "we're not ready yet" at the end, you'll learn to reverse-engineer these concerns into discovery questions that make closing feel natural and almost anticlimactic.

I'll walk you through my proven 4-step process to transform your discovery from a technical fact-finding mission into the real close of your 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

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

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

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

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

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

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