Driving Healthcare outcomes by connecting leaders with high-impact talent | Founder at Talenta | CHRO

Chief HR Officer. Executive Recruiter. Founder. Business Builder.

The game of business is the challenge of a lifetime — and the one I keep coming back to.

I’ve built my career on a clear conviction: companies that scale well are led well. In private equity, founder-led, and high-growth environments, leadership and people systems determine whether momentum compounds or stalls.

I serve as Chief HR Officer at Premier Roofing, a Denver-based, Aurora Capital–backed business scaling in a fiercely competitive market. Alongside that, I run Talenta HR Group, my boutique firm helping PE-backed companies solve their toughest people challenges through executive search, fractional CHRO support, and talent strategy advisory.

I also created TalentSignal— an AI-powered recruiting visibility tool that helps growth companies uncover brand blind spots, benchmark funnels, and attract the right talent faster.

What you’ll find here: sharp takes on talent, performance, private equity, and business in general. Wins, mistakes, and the occasional contrarian view.

If you’re building something ambitious — or wrestling with the friction of scale — my DMs are open.

Alden Pennington

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.

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.

My wife sent me this from the boys’ Valentine’s Day fundraiser at school.

Every kid got a budget to buy stuff — s’mores, keychains, smoothies, cookies. Typical kid stuff.

Our youngest spent his budget on roses for mom.

He’s watched me bring her flowers and knew exactly how happy it makes her. Did it completely on his own.

Definitely a proud dad moment.

Hope everyone has a great Valentine’s Day!

(P.S. Our oldest was too busy generating sales at his booth to buy flowers. That’s a different kind of proud dad moment.)

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.

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.

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

Last year, we found out my son has dyslexia and ADHD.

As a parent, you sit in those meetings with the school and every single one is about what your kid can't do. Three meetings. Four meetings. Not once did anyone say, "Here's what he's great at."

I left one of those meetings and told my wife: I know for a fact that for every one of these things, there's a flip side. And nobody's looking for it. All we hear about is what he's not good at. 

Then I remembered that David Rendall—someone I've known for years—had a lot of content out there about embracing your weaknesses. 

I went to his website and watched one of his speeches. Then had my wife watch. She sent it to other moms. Then we watched it with our boys. 

By the end, my other son said, "I want ADHD."

So, you could say the message landed.

Dave's got a PhD in organizational leadership and he's spent his career proving one thing: your weaknesses are inseparable from your strengths. Every superpower has a downside. That's what makes it a superpower. And every downside has a superpower. 

The problem? Schools, therapists, and managers are wired to fix weaknesses. Nobody's wired to find the strength hiding inside them.

I brought Dave on the podcast and we went deep:

→ Why the people with the most potential are often the ones getting crushed by the system

→ What Paul Orfalea (founder of Kinko's, who struggles to read and write) teaches us about success

→ How my wife and I use our polar opposite wiring to make one plus one equal three

This one's personal. And it might change how you see your kids, your team, or yourself.

Listen now: https://lnkd.in/eHnfYFe2

Someone on my sales coaching call froze mid-question last week.

A prospect had just said something interesting and it was the perfect moment to dig deeper. 

But instead of asking the obvious follow-up, they hesitated, fumbled around, and then moved on to another questions.

Later they told me: "I thought we weren't supposed to ask 'why' questions. I heard it from Chris Voss."

According to Voss, who was a skilled negotiator for some of the most high pressure hostage-type situation, asking 'why' makes people defensive.

And look, I love Voss. Never Split the Difference should be required reading.

But this is what happens when we turn principles into rigid rules for salespeople.

They make conversations weird. 

Look, Voss was negotiating with terrorists.

Actual life-or-death hostage situations where conflict is baked into every interaction. When someone's holding leverage over you, "why" can absolutely make them defensive.

But you're not in a hostage negotiation when you're talking to prospects.

You're in a consultative sales conversation where the prospect theoretically wants help solving a problem.

The issue isn't the word "why."

It's whether you're asking from a position of accusation or curiosity.

"Why do you guys do it that way?" delivered with genuine interest? That's a great question.

"Why would you do THAT?" with judgment in your voice? That creates defensiveness.

The difference is tonality, not vocabulary.

When we follow rules without understanding the context they came from, we tie our own hands. We stop thinking critically about what the situation actually needs.

I recorded a 10 min podcast on this. In it, you have full permission to use "why"—and I explain:

→ When hostage negotiation advice doesn't apply to sales
→ The tonality markers that make "why" questions land well
→ How to ask from curiosity instead of judgment

Full episode: https://lnkd.in/eKMDfgGe

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.

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.

More is not better. Even when it comes to "adding value" in your pitch. 

There's something called the goal dilution effect. 

University of Chicago researchers ran 6 experiments on how people view benefits. 

They discovered that adding additional benefits to something resulted in people viewing each benefit as less valuable. 

They ran 6 experiments to validate it. 

I wrote an article sharing more on it and what it means to your sales pitch. 

Here it is: https://lnkd.in/gxSg7Fdh

Playboy, pizza, and politics. He marketed them all at the highest level. 

He ran the agency that created the famous Apple "1984" commercial. 

In an AI-world, he says marketing as an industry is all but dead. The first industry that will be consumed by AI. 

And he has a strong opinion on what that means to the competitive landscape of business. 

Shifting winners from those that have superior strategy and planning to those that have superior execution and agility. 

We cover all this, and a lot more. 

The real story behind Apple's 1984 ad and how it almost never aired

What the OODA loop is and why it matters more than ever today, from a former fighter pilot's perspective. 

And a lot more. 

Listen to my conversation with Bob Perkins here: https://lnkd.in/eg28qA5z

What's it take to really dominate in your field? 

Any field. Golf, sales, MMA, business, fighter pilots. 

Talent? Sure, it matters. But a lot of talented people fail. 

So, what is it? 

Success leaves clues. And I talked to Bob Perkins (ex-marketing chief at Playboy, Pizza Hut, Calvin Klein) about what it really takes to dominate your field.

He shared Tiger Woods' answer to the same question. 

What do you think?

I still can't believe they ran this as a Super Bowl ad. It's the dumbest ad I've seen in a long time. 

It represents every ounce of how AI is being misunderstood and misused in business today. And they paid millions of dollars to put their name on it and broadcast it to the world. 

What this basically says: 

To the employee: I can use AI to be lazy and phone it in.

To the employer: We can use AI to replace all those lazy-asses already phoning it while working at home. 

And, best of all, any idiot can do it with a simple prompt... and voila! Work without work. 

This mindset is exactly why 95% of AI initiatives fail to produce ANY ROI at all. And that's not me speaking, that's MIT. And dozens of other sources. 

Because of this limited mindset around using AI. 
If that's how you're looking at AI, you are missing the boat. 

You're trying to get a little more efficient (or lazy) at the game being played today. Oblivious to the fact that the game is changing. 

If you're using AI to squeeze a little more out of old processes, systems, and jobs, you may see some temporary improvements. 

But you're getting a little better in the “horse and buggy” industry in the 20s, while someone else is building gas stations.

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.

Why do some founders feel like they’re paddling upstream and others seem to be pulled forward by a sail? 

It down to beliefs, not effort. 

I see this pattern quite a bit: smart, driven business owners who can't break through a current revenue ceiling.

Maybe $1m. Or $5M a year. 

They hire consultants, agencies, try new tactics, work even harder.

Nothing moves.

Hell, I've been this business owner. 

Meanwhile, other founders seem to scale with what looks like ease.

The difference isn't effort.

It's the underlying belief systems that determine where the effort goes. 

The stuck founder believes things with absolute certainty that simply aren’t true.

Could be "I need to be in every client conversation" or "our market is too small" or "that channel doesn't work for us."

Could even be, “The harder things are, the more progress I’ll make.” 

They're so certain they're right that they don't even question it.

And because they're operating under a false assumption, every ounce of effort goes toward fighting against how things actually work.

Which is why no amount of effort will make a difference. 

The question isn't "am I working hard enough?"

It's "what am I dead certain about that might not be true?"

I recorded a quick podcast breaking down: 

→ The most common false beliefs that cap growth (including the one that held me back for years)

→ How to identify which assumption is costing you millions

→ What separates founders who scale from founders who plateau

Check it out here: https://lnkd.in/eCpt5-i7

If everyone on your team agrees with your decisions, you're not leading. You're just there.

The decisions where everybody's happy—where there's consensus, where nobody pushes back—those don't require leadership.

That's just collective agreement.

Where you actually add value is when people push back. When the person across the table doesn't necessarily agree with the decision. When you're 65% sure about something, and make the call anyway.

In every business, there are conversations that need to be had--and aren't. 

A behavior that needs to be addressed. 
A practice that needs to be stopped. 
A person that needs to be fired. 

Ben Horowitz (VS & author) calls it management debt.

Every conversation you dodge, every underperformer you keep, every broken process you tolerate--it compounds. Silently. In the background. Just like financial debt.

And eventually the interest payments come due. Good people leave, culture rots, growth stalls.

Our job as leaders isn't consensus-building.

It's making the calls everyone else is avoiding.

I broke down the concept of management debt, why it happens, and what to do about it in an article you can read here: https://lnkd.in/gWYYHaf4

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.

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Alden Pennington

Ray J. Green

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The Battle

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