Robbie Crabtree

Storyteller in tech. Previously did it as a trial lawyer with 102 jury trials. 

Co-Founder

Repeatable Client Acquisition & Fulfillment | Our mastermind community helps you convert online income into a real business | Book a call or DM to apply

I'm an operator documenting what I've learned building revenue engines over the past decade.

CEO @ MSP Sales Partners. Managing Partner @ Repeatable Revenue. Former PE-backed CEO. Former Managing Director at the U.S. Chamber of Commerce. Spent six years building sales systems for Robin Robins (TMT, sold to PE). Built revenue engines for 100+ service businesses.

I write about what I've learned: how sales systems actually scale, the difference between activity and productivity, why hard choices matter more than hard hours, building a business without burning out.

This isn't guru content. It's lessons from the work... what I got wrong, what finally clicked, patterns I see across businesses, frameworks that actually held up under pressure.

I write for three types of people: Strategists thinking about exits and scale. business owners stuck at a plateau trying to break through. Thinkers who want to build intentional lives, not just businesses.

If you're one of those (or all 3), follow along.

Ray J. Green

Whatever happened to Chris Walker?

He was the top B2B marketer and reshaped how the entire market thought about marketing. Built Refined Labs from the ground up and went from $1M to $20M in 18 months. Worked with 350+ software companies. He put demand generation on the map. Created incredible returns for investors and helped hundreds of people accelerate their careers. 

Then he walked away.

Now he's talking about something very different: Frequency.

And no doubt people are wondering, "What the hell? Is Chris a spiritual coach now or something? Did he go on some DMT trip?"

I had him on the podcast this week and asked him some candid questions about this journey.

And he shared some things that may not surprise you if you're a builder. 

He said at the peak — $22M in revenue, 12-14 hour Zoom days, running away on vacation every 90 days and coming back to 1,000 emails — he realized he'd done everything he was "supposed" to do. And it didn't feel at all the way he thought it would.

I related to that more than I'd like to admit.

I left a PE-backed CEO job, moved my family to Cabo, and 18 months later felt the exact same way I did before. Different wallpaper. Same foundation.

Chris has a framework for why this happens — why we keep repeating the same patterns with new circumstances. New job, same toxic cycle. New business, same trap. New relationship, same dysfunction.

In this episode we get into all of it:

→ Why achieving your goals can be the worst thing that happens to you

→ The invisible architecture underneath every decision you make

→ Why Chris believes this will be as mainstream as exercise within 5 years

Whether you buy it or not, this conversation will make you think.

Listen now: https://lnkd.in/esM-S9w7

CEO @ MSP Sales Partners | Man. Partner @ Repeatable Revenue | Ex-PE Backed CEO | Former U.S. Chamber Managing Director

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Something weird is happening in outbound sales right now.

The more AI gets used for cold outreach — calls, emails, DMs — the worse it's getting for everyone using it. And the better it's getting for anyone who sounds like an actual person.

We manage 50+ SDRs making cold calls for MSPs right now. And the ones getting the best results aren't the most polished. They're the most HUMAN.

They pause. They laugh. They say "honestly, this is a cold call" and give the prospect permission to hang up. They go off-script when something the prospect says is worth following.

And people respond to it. Because after getting five AI-generated LinkedIn messages and three robotic voicemails before lunch, a real voice with a real personality feels different.

This is why the "hire cheap, hand them a script, pound out as many calls as possible" approach is failing harder than ever. You're competing against AI with a person who sounds like worse AI.

The SDRs booking 8, 10, even 20 appointments a month in our fractional sales management program aren't reading scripts verbatim. They have frameworks — but they're trusted to be a human within those frameworks. To personalize an email. To riff on a conversation. To respond to a DM like a normal person instead of a chatbot.

That requires a different caliber of hire. And it changes how you think about the entire role.

I recently put together a playbook breaking down three specific SDR strategies behind the MSPs getting outsized results right now — full frameworks, scripts, and campaign templates. These are real-world, actually working right now case studies. 

Grab it for free in our MSP Sales Toolbox at www.MSPSalesToolbox.com.

We manage 65 SDRs right now for MSPs across North America.

We've hired and trained over 100 in the past 12 months. 

And when a new MSP comes into our program, the first thing we do is score them on a report card.

Because we can predict — with a very high degree of confidence — whether an SDR is going to produce or flop before they ever pick up the phone.

There are 5 patterns that show up almost every time someone's getting goose eggs:

→ They hired anyone with a pulse. Cheapest person, barely screened, "just read the script." The difference between a good SDR and a great one isn't 10-20%. It's 2-5x.

→ They think they have a good list — and they don't. Raw vendor data has 30-40% breakage. So take whatever you'd expect from your SDR and discount it by a third.

→ They have no offer. "Will you meet with my CEO for 15 minutes?" is not a pitch. It's a prayer.

→ Their scripts are from 2019. Permission-based openers are working right now. Shorter scripts. More human. If your SDR sounds like a bot, they'll get treated like one.

→ Zero sales infrastructure. No call reviews. No meetings. No accountability. Even a good SDR will decline in a vacuum.

0 for 5 on these? You're going to lose money.

When onboarding clients, we grade all 5. Because we know we have some work to do if they fail across the board.

The good news? Even C's in each of these areas get you positive ROI.

If you have A's, you're baffled what people mean when they say, "Cold calling doesn't work anymore." 

If you want to know what that looks like, I created a playbook with 3 detailed case studies of MSPs consistently getting 10-15 appts a month right now. 

Frameworks, scripts, strategies. 

Grab it for free at www.MSPSalesToolbox.com.

Every call your SDR makes is producing 2 things.

The first one's obvious — either an appointment or not.

The second one most MSPs throw away: Market intelligence.

When a prospect tells your SDR "we already have an MSP and we're happy," that's not a dead end. That's data. That tells you this person has budget, understands managed services, and has already made the buying decision once. They're a future buyer. You just don't know when.

When someone says "we handle IT internally," that tells you something different. They haven't bought managed services before. The sale isn't switching providers — it's educating them on why they need one at all.

Two completely different prospects. Two completely different marketing approaches. 

But if your SDR logs both as "not interested" and moves on, you've lost the distinction — and the ability to do anything with it.

The MSPs getting outsized results from their SDRs aren't just using them to book meetings. They're using every call — including the ones that don't convert — to build an intelligence layer that feeds their marketing for months.

Specific dispositions. Tailored sequences. Content that matches the prospect's actual situation, not a generic drip campaign that treats everyone the same.

Your SDR talks to hundreds of prospects a month. Each one is telling you exactly what they need to hear. The question is whether you're set up to listen.

I put together the full disposition framework and email sequences in a playbook with three SDR case studies.

Free at www.MSPSalesToolbox.com.

If somebody cold calls you and asks for 15 minutes on your calendar, what are they actually asking for?

Your most expensive resource, time.

And I don't know about you, but someone has a better chance of getting my credit card than my calendar. I have more money to give than I do time.

And so do most of the people you're trying to get appointments with. 

Which means the SDR role is a sales job. A real one. They're selling something — and the price the prospect pays is their TIME.

So "would you like to meet with my CEO for 15 minutes?" ins't a very compelling offer on its own. It's an ask with no upside for the person you're asking. 

Sure, you'll get some appointments with that pitch. A blind squirrel finds an acorn every once in awhile. But you won't get consistent returns. Not very good ones anyway. 

The MSPs I've seen consistently book 10, 15, even 20 appointments a month? It's not because their SDRs are smooth talkers with a magic script. They simply arm their SDRs with with something worth "buying." 

A toolkit. An audit. A benchmark study. Something specific to the prospect's problem — where the meeting is worth attending. Because there's some value for the prospect to gain by saying yes and showing up. 

Same SDR. Same list. Same market. If you have a compelling offer to go outbound with, you'll see completely different results.

Because one has something to sell and the other is just asking for time.

I gave a talk on this recently to a couple hundred MSPs — broke down 3 detailed case studies of SDR strategies that are producing 3-5x more appointments than the industry average right now. We turned it into a full playbook with the frameworks, scripts, and campaign templates.

Just dropped it in our MSP Sales Toolbox — grab it free at www.MSPSalesToolbox.com.

Hot lunch date with this pretty lady to celebrate some good heart health news! ❤️

Before your SDR makes another call, try this.

Read the script out loud. The whole thing. Then ask yourself one question:

Would I take that meeting?

Not "do I think someone who needs IT services [or whatever you sell] take it." Would YOU — busy, skeptical, protective of your calendar — stop what you're doing and book 15 minutes based on what you just heard?

If the answer is no, you've found the problem. And it's not the SDR.

I've managed salespeople for 25 years across a dozen industries. The pattern is the same everywhere. When the offer is weak, we blame the caller. We blame the list. We blame the market. "Cold calling doesn't work anymore."

Cold calling works fine. Sure, it takes more skill than it used to to make contact. But it works. I have 60+ SDRs calling outbound for MSPs in our business. It works. 

But what you're offering on the call doesn't.

Because a meeting isn't free.
The prospect pays with their time.

And for most business owners, someone has a better chance of getting their credit card than their calendar. Time is the scarcer resource.

Most SDR pitches don't come close to justifying that price.

The fix isn't playing musical chairs in the SDR seat. Or looking for that magic script. Or paying for 15 more tools.

It's giving your SDR something worth selling — where the meeting is the delivery mechanism, not the ask.

I recently shared three case studies on stage with a couple hundred MSPs — the specific strategies behind SDR teams booking 15-20 appointments a month right now. We turned it into a full playbook with the frameworks, scripts, and templates behind each one.

It's free in our MSP Sales Toolbox at www.MSPSalesToolbox.com.

How many great coaches were great players?

Bill Belichick never played a snap in the NFL. Phil Jackson averaged <7 points a game. Tony La Russa hit .199.

Meanwhile, Wayne Gretzky — the greatest hockey player who ever lived — coached the Coyotes for 4 seasons and never made the playoffs. 

Same thing happens in sales.

Business owners hire their best closer and hand them the manager title. Makes sense on paper — this person knows how to sell, so they'll teach everyone else.

Except selling and managing are 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝘀𝗸𝗶𝗹𝗹𝘀𝗲𝘁𝘀.

Your top seller is selfish by design. That's what makes them great. They focus on their numbers, their pipeline, their commission check.

A good manager? They build systems. They transfer knowledge. They coach — and coaching isn't just finding 10 things you did wrong on a call. It's identifying the 𝗼𝗻𝗲 𝗵𝗶𝗴𝗵-𝗹𝗲𝘃𝗲𝗿𝗮𝗴𝗲 𝘁𝗵𝗶𝗻𝗴 that needs to change and following up until it does.

In my experience, best managers were usually good, not great at sales. They usually come from the middle of the pack as salespeople.

Not because they couldn't sell. Because they understood the game well enough to teach it.

Belichick never played a down in the pros. But he understood defense better than anyone who ever suited up.

If you're hiring a sales manager, stop looking for your best closer. Start looking for someone who can explain 𝘄𝗵𝘆 they're good — and prove they've made others good too.

When your SDR doesn't book an appointment, what gets logged in the CRM?

For most MSPs, it's some version of "not interested." Maybe "no answer." Maybe nothing at all.

That tells you absolutely nothing. And it wastes the most valuable thing that call produced — the reason they said no.

The MSP in our program booking 15-20 appointments a month doesn't log "not interested."

They log why.

Happy with their current MSP. Locked into a contract. Handles IT internally. Doesn't think they have a problem. Bad timing. Already shopping.

Five to seven specific dispositions. Each one captured in a custom field in the CRM. And each one triggers a completely different email nurture sequence.

Because the prospect who's happy with their MSP needs different marketing than the one who's locked in a contract. The person who handles IT internally needs a different set of stories and case studies than the one who says the timing's off.

"Not interested" gets the same generic follow-up as everyone else — if it gets anything at all. A specific disposition gets months of tailored content designed to shift that exact objection. Subtle, not pushy. Case studies, not pitches. Seeds planted over time.

And when the SDR calls back at the end of that sequence, they're not making another cold call. They're calling someone who's been receiving content that speaks directly to their situation for months.

Same lead. Completely different conversation.

I broke down the full disposition framework — including example emails for each stage — in a playbook with three SDR case studies.

Grab it free at www.MSPSalesToolbox.com.

Hiring an outside sales rep is a really expensive bet for MSPs. 

You post the job. You interview people who are professionally good at interviews. You pick the one who sounds best. You pay them well because good salespeople know their worth. You train the best you can. You give them 4-6 months to ramp.

And you cross your fingers.

Because you don't know what this person is actually like until they're in the seat — talking to your prospects, representing your company, handling objections in real time. Interviews and personality tests simply don't tell you everything you need to know about that. 

One MSP in our program solved this by never hiring outside sales reps at all.

They grow every salesperson from the SDR role. By the time someone's ready to run a discovery call or present a proposal, that person has already been in the building for a year or more. They've made thousands of calls. They've been to trade shows and conferences. They've shadowed dozens of sales meetings. They've taken on qualifying calls and proven they can handle the conversation.

You already know what they're made of. You're not even really making a bet at that point. You know the outcome. 

And the salespeople who come up this way tend to stick around longer. They came up through the system. They know the culture. They weren't recruited away from somewhere else by a slightly bigger paycheck — which means they probably won't leave for one either.

It takes patience. But it's a hell of a lot less risky than the resume lottery.

I shared details on this to a mastermind of a couple hundred MSPs recently. And I put the development framework they use — phases, milestones, and red flags — along with a couple other case studies of success SDR strategies into a playbook. 

You can grab it here: www.MSPSalesToolbox.com.

And if you ARE recruiting for the outside sales role and want some help, shoot me a DM.

True story.

I increased my VO2 max by 50% in less than 60 days. Without changing what I ate. Without exercising any more. Without doing a single thing differently.

Quick context:

I've tried to improve my VO2 max for a decade. It's one of the key markers of cardiovascular health.

I ran half marathons. I did Muay Thai 6 nights a week. I trained for triathlons. Sometimes all at once.

My VO2 max barely moved.

Apple Health had me at "Below Average" for as long as I've owned my Watch.

So what changed 2 months ago?

I started taking beta blockers.

We discovered a heart condition that's substantially improved by beta blockers, which slow down the heart rate. 

I'm not a doctor, so I don’t know exactly how they work. But  the results speak for themselves.

I changed 𝗻𝗼𝘁𝗵𝗶𝗻𝗴 else. Diet, sleep, exercise — all the same. And my cardiovascular markers are the best they've ever been, and climbing. 

Because for 10 years, I was applying the wrong solution to the problem.

I thought I knew what the problem was. I thought more effort was the answer. But I was treating a 𝘀𝘆𝗺𝗽𝘁𝗼𝗺, not the root cause.

Which means no amount of pushing was ever going to fix it.

It's a good reminder:

If something in your business requires a disproportionate amount of effort and still isn't moving — maybe the answer isn't pushing harder.

Maybe you haven't diagnosed the real problem yet.

I've never hired a Level 1 tech. But I think this metaphor holds.

If you needed to hire someone for an entry-level IT role — something where most of the work is teachable and trainable — you still wouldn't hire the cheapest person who's never turned on a computer and doesn't like technology.

Even though the job itself is learnable, you'd still want someone who's a decent fit. Someone curious. Someone coachable. Someone who actually wants to do this kind of work.

The same thing holds for sales.

If you want to hire an SDR that actually gets a return on your investment, you aren't looking for the cheapest person you can find with a pulse.

Yes, it's entry-level sales. Most of it is teachable. But there is a huge difference between someone who's going to be good at this job and someone who's going to suck at it.

Are they a decent communicator? Can they do repetitive work without mentally checking out? Do they have the emotional resilience to get rejected 30 times in a morning and still bring energy to the next call?

Not everyone can. That's fine. But if your hiring criteria is "doesn't want much money, shows up remotely sober, and can kind of read a script" — don't be surprised when it doesn't work out. 

The difference between a good and great SDR isn't 10-20%. It's 2-5x. And that math starts at the hire.

I broke down the hiring patterns, scripts, and campaign strategies behind MSPs booking 3-5x more appointments in a full playbook — three detailed case studies with templates.

Free in our MSP Sales Toolbox at www.MSPSalesToolbox.com.

For outbound, no list is actually better than a bad list you think is good. 

Sounds wrong. But hear me out.

If you have no list, you know you have a problem. You'll go build one, buy one, scrape one. You'll put in the work because it's obvious you have a problem.

But if you have a list from a reputable vendor — thousands of records, company names, phone numbers, titles, all of it looking clean in the CRM — you feel prepared. They sell you on "99% accurate data." You feel like the foundation is set. 

And you hand that list to your BDR or SDR and say go.

Except 30-40% of the contact data on a raw vendor list is wrong.

Maybe the company info is fine. The address, website, standard information.

But the right contact and phone number? Not so much. And those are the 2 fields that matter most on a cold call.

So your SDR starts dialing and 1/3 of the calls go nowhere. Their results look like crap. You start questioning whether they're the right person. Maybe whether outbound works at all.

And the whole time, the diagnosis is wrong. Because you assumed the list was good since it came from [ZoomInfo, Seamless, Apollo, name your vendor]. 

The worst position to be in isn't not having data. It's having data you believe is good when it isn't. Because it sends you looking for problems everywhere except where the actual problem lives.

Every outbound strategy starts with the list. Yes, the script matters. The person calling matters a lot. And the offer they're pitching definitely matters.

But if the data's broken, everything downstream of it is broken, too. 

I put together a full playbook on the SDR strategies producing outsized results for MSPs right now — three case studies with frameworks, templates, and campaign breakdowns.

Grab it free at www.MSPSalesToolbox.com.

Every few years, someone declares a sales channel dead.

Cold calling is dead. Email is dead. Direct mail is dead. Door-to-door is dead.

And then you meet someone quietly crushing it with that exact channel. What happened?

They adapted the tactic. Because THAT is what actually changes. 

I've worked across 12 industries over 25 years. The pattern is always the same. The psychology of how people make buying decisions barely moves.

We still want to feel understood. We still respond to specificity over generic pitches. We still give our attention to people who earn it instead of demand it.

That's been true for decades. It'll be true for decades more.

What changes is the environment. New technology. New screening tools. New noise levels. AI flooding the zone with volume-based outreach. And so the tactic that worked three years ago stops working — not because the channel broke, but because the context shifted and the approach didn't.

The people who declare a channel dead are usually the ones who stopped updating how they use it.

Right now, the SDRs in our program booking 5, 10, even 20 appointments a month for MSPs are still cold calling. Still emailing. Still sending direct mail. They're just doing it differently than they were two years ago. And they'll do it differently again next year.

The channel isn't the variable. Your willingness to keep adapting is.

I broke down the specific strategies, scripts, and campaigns behind those results in a full playbook — three case studies with templates you can steal.

Grab it free at www.MSPSalesToolbox.com.

Most MSPs measure their SDR's performance like a microwave.

Drop prospects an email or mailer. Make a few calls. Measure the immediate results. 

Did we get appointments this week? No? Shit. Try again in 6 months. Start over. 

It's the Hot Pocket approach. Quick, instant gratification.

And when you think about it like this, you'll get "something" — but it might be frozen in the middle and too hot on the edges.

The MSPs I've seen get the biggest returns from their SDRs think about it more like a Crockpot.

They run the same initial campaign everyone else does. They make the same calls. And they accept that 95% of those calls aren't going to book an appointment — just like everyone else.

The difference is what they do with the 95%.

They take a longer term outlook. They're more patient and measure results over a longer period of time. 

Because instead of tossing those leads back into a pile and calling them cold again in six months, they capture the reason the prospect said no, feed them into a highly customized nurture system based on that outcome, and call them back months later with more context, more awareness, and a much warmer conversation.

That callback converts at SUBSTANTIALLY higher rates than the first cold call ever could.

Because now you're calling someone who knows your name, has seen your content, and has had time for their situation to change. 

It takes longer. It's not instant gratification. But the difference between Hot Pocket ROI and Crockpot ROI on your SDR investment is massive. 

I have actual data on this, and it produces 3-5x returns on the next call back. 

I recently broke down this exact strategy — and two others — in a talk to a couple hundred MSPs. We turned it into a full playbook with the email frameworks, callback scripts, and campaign templates.

Free in our MSP Sales Toolbox at www.MSPSalesToolbox.com.

Here's a quick test for whether you hired the right SDR.

Could you hand a few leads from an event and trust them to follow-up without reviewing every message first? 

Assuming they're fully ramped up and trained, if the answer is no — if you wouldn't trust them to modify an email, personalize a message, or respond to a prospect without a script in front of them — you have a problem.

Most likely, a hiring problem. 

Because the SDR strategies that are working right now require exactly that kind of trust.

Multi-channel campaigns where the SDR is calling, emailing, connecting on LinkedIn, sending voice notes, following up on DMs. Each touchpoint references the last. Each one needs to feel human, not templated.

You can build playbooks for this. You can role-play scenarios. But you cannot script every detail of every interaction across five channels over 30 days. The person in the seat has to be able to think. And to be HUMAN. 

And if your hiring criteria was "cheapest person willing to dial" — that person probably can't.

The MSPs getting 3-5x more appointments in the IT industry right now aren't just tweaking scripts and lists. They're raising the bar on who sits in the chair.

I put together a full playbook on the SDR strategies behind these results — three case studies with frameworks, templates, and campaign breakdowns. But they require having the right person. 

You can grab it (and a bunch of other sales tools) for free at www.MSPSalesToolbox.com.

And if you need help finding the SDR who will execute at this level and actually create pipeline, just send me a DM.

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Ray J. Green

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The Battle

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