Stay ConnectedMeet Gabe Lullo.
Gabe Lullo is the CEO of Alleyoop, a sales development agency working with industry giants such as ZoomInfo, Salesloft, and Adobe.
He has trained over 8,000 salespeople across diverse businesses and, during his tenure in Alleyoop, he has personally hired and managed more than 1,500 SDRs.
With over two decades of experience in sales, marketing, and executive recruitment, his strategies have significantly driven Alleyoop’s growth.
"The GTM bar is quite low. And that's a good thing for those of us who get it." - Neil Weitzman, Fractional CRO and Founder of Weitzman Go to Market
Neil's philosophy comes down to three words: get it done.
Not more frameworks, not more slide decks, just execution.
His take on the say-do ratio is simple:
If you say you're going to do something, do it.
If you can't, communicate it before someone has to ask.
Sounds obvious. Yet most companies still miss the mark.
The follow-up that never comes, the quote promised on Tuesday that's still sitting in the drafts on Friday. The proposal that takes two weeks instead of two days.
Neil's point: the bar is so low that simply doing what you say you'll do already puts you ahead of most of the market.
When he joins a company as a Fractional CRO, he starts with the data.
Do they know what good looks like in their funnel?
What's converting? Where are deals getting stuck?
Most companies have fragments of the answer.
Very few use that information to coach, hire, and improve consistently.
Build the foundation, create repeatable systems, get the team running, and eventually hand it off to a full-time leader.
And for founders who say they want honest feedback?
He'll give it.
The best ones are willing to hear it.
"You still have to have some form of human personalization. You still have to pick up the phone. You still have to build relationships." - Sam Hollander
That's Sam Hollander's view on AI in sales.
Not because he's anti-AI. Quite the opposite.
After 18 years building revenue in markets where the traditional playbook doesn't exist, he's seen firsthand where technology helps and where it doesn't.
He's led two companies through successful exits, and his first 90 days always look the same: talk to customers, pressure-test the messaging, and build operating structure.
Because in startups, ambiguity is the biggest challenge. The only way through it is to create your own anchor.
When it comes to outbound, Sam doesn't think the answer is more automation.
At a conference last month, he watched a friend open her inbox:
1,000 unread emails from vendors.
Just sitting there.
That's why he's building LynkUp, a marketplace that connects high-intent buyers and sellers at conferences, turning random badge scans into intentional, confirmed meetings.
The biggest deals of his career didn't start in an email sequence. They started in person.
His advice for enterprise sales is simple: map stakeholders early, identify champions and blockers, and stay in touch consistently. Momentum matters.
AI is great for saving time.
Great for research, writing, and prep work.
But relationships still close deals.
"You still have to have some form of human personalization. You still have to pick up the phone. You still have to build relationships." - Sam Hollander
That's Sam Hollander's view on AI in sales.
Not because he's anti-AI. Quite the opposite.
After 18 years building revenue in markets where the traditional playbook doesn't exist, he's seen firsthand where technology helps and where it doesn't.
He's led two companies through successful exits, and his first 90 days always look the same: talk to customers, pressure-test the messaging, and build operating structure.
Because in startups, ambiguity is the biggest challenge. The only way through it is to create your own anchor.
When it comes to outbound, Sam doesn't think the answer is more automation.
At a conference last month, he watched a friend open her inbox:
1,000 unread emails from vendors.
Just sitting there.
That's why he's building LynkUp, a marketplace that connects high-intent buyers and sellers at conferences, turning random badge scans into intentional, confirmed meetings.
The biggest deals of his career didn't start in an email sequence. They started in person.
His advice for enterprise sales is simple: map stakeholders early, identify champions and blockers, and stay in touch consistently. Momentum matters.
AI is great for saving time.
Great for research, writing, and prep work.
But relationships still close deals.
"Do you have the grit necessary to see it through? That's where I see a lot of people struggle." - Zack Schneider, Founder of Agency 15
Zack started his first agency at 19. Not because he had a plan, but because he had nothing to lose. By 26, he had scaled it to an exit.
He'll be the first to tell you that naivety was the advantage.
At Agency 15, every team member keeps a carabiner on their desk with 30 fundamentals on it.
Not values. Fundamentals. Specific, observable behaviors that managers can coach in real time.
One fundamental each day. Every day.
Until they stop being reminders and become habits.
Today's fundamental: Practice blameless problem solving.
Apply your creativity to solutions, not finger-pointing.
Learn from mistakes faster than everyone else.
Simple doesn't mean easy.
In fact, most of the things that actually work are surprisingly simple.
The biggest leadership lesson Zack learned came later.
Growing the company wasn't about strategy.
It was about replacing himself, over and over again, with people who were better than him at the things he used to do.
He compares it to mountain climbing.
As the altitude changes, some people adapt and keep climbing with you.
Others reach a level where they can't go any higher.
That doesn't diminish what they contributed.
It just means they aren't the right people for the next stage of the climb.
The companies that succeed aren't built by people who never struggle.
They're built by people with the grit to keep climbing anyway.
"Do you have the grit necessary to see it through? That's where I see a lot of people struggle." - Zack Schneider, Founder of Agency 15
Zack started his first agency at 19. Not because he had a plan, but because he had nothing to lose. By 26, he had scaled it to an exit.
He'll be the first to tell you that naivety was the advantage.
At Agency 15, every team member keeps a carabiner on their desk with 30 fundamentals on it.
Not values. Fundamentals. Specific, observable behaviors that managers can coach in real time.
One fundamental each day. Every day.
Until they stop being reminders and become habits.
Today's fundamental: Practice blameless problem solving.
Apply your creativity to solutions, not finger-pointing.
Learn from mistakes faster than everyone else.
Simple doesn't mean easy.
In fact, most of the things that actually work are surprisingly simple.
The biggest leadership lesson Zack learned came later.
Growing the company wasn't about strategy.
It was about replacing himself, over and over again, with people who were better than him at the things he used to do.
He compares it to mountain climbing.
As the altitude changes, some people adapt and keep climbing with you.
Others reach a level where they can't go any higher.
That doesn't diminish what they contributed.
It just means they aren't the right people for the next stage of the climb.
The companies that succeed aren't built by people who never struggle.
They're built by people with the grit to keep climbing anyway.
"We tell our stories because we do not heal in isolation. We need each other." - Tom Farley, Recovery.com
Tom will tell you upfront that he doesn't walk into a room to motivate anyone.
He walks in because he needs to be there just as much as the person sitting across from him.
He grew up in a big Irish family in Madison, Wisconsin, where drinking was just how you handled anything uncomfortable.
By the time he got to Georgetown, then Wall Street, he had built an entire identity around being sharp, polished, and put together, with no idea how hollow it felt underneath.
The moment that cracked something open came before his own recovery.
He went to an AA meeting with his brother Chris Farley, in a basement in Hell's Kitchen, and watched him stand up and be more honest than Tom had ever seen him, in front of a room full of strangers.
He didn't understand it yet. But he never forgot it.
Years later, when he found his own way into recovery, he finally did.
The only place he has ever felt real belonging wasn't his family, his career, or his religion. It was a church basement with people he never would have thought to sit with otherwise.
He's been to recovery centers, prison programs, veterans' groups, and boardrooms since.
What he keeps finding is the same thing: people don't lack the desire to get better. They lack permission to be honest about where they actually are.
His take on stigma is simple.
It comes from fear, and the only way through it is real human connection, not awareness campaigns, not likes or shares, but someone looking you in the eye and saying, I've been there too.
"Recovery exists on the other side of fear. Every time you walk through it instead of drinking it away, you get stronger."
"We tell our stories because we do not heal in isolation. We need each other." - Tom Farley, Recovery.com
Tom will tell you upfront that he doesn't walk into a room to motivate anyone.
He walks in because he needs to be there just as much as the person sitting across from him.
He grew up in a big Irish family in Madison, Wisconsin, where drinking was just how you handled anything uncomfortable.
By the time he got to Georgetown, then Wall Street, he had built an entire identity around being sharp, polished, and put together, with no idea how hollow it felt underneath.
The moment that cracked something open came before his own recovery.
He went to an AA meeting with his brother Chris Farley, in a basement in Hell's Kitchen, and watched him stand up and be more honest than Tom had ever seen him, in front of a room full of strangers.
He didn't understand it yet. But he never forgot it.
Years later, when he found his own way into recovery, he finally did.
The only place he has ever felt real belonging wasn't his family, his career, or his religion. It was a church basement with people he never would have thought to sit with otherwise.
He's been to recovery centers, prison programs, veterans' groups, and boardrooms since.
What he keeps finding is the same thing: people don't lack the desire to get better. They lack permission to be honest about where they actually are.
His take on stigma is simple.
It comes from fear, and the only way through it is real human connection, not awareness campaigns, not likes or shares, but someone looking you in the eye and saying, I've been there too.
"Recovery exists on the other side of fear. Every time you walk through it instead of drinking it away, you get stronger."
"The brand is the most important thing. Everything you put out into the universe has to align with your three pillars. And if it doesn't serve you, cut bait and move on." - Brianne Price, CPG Executive and Chief Revenue Officer
Brianne didn't get into consumer brands from a business school case study.
She got in from a salon floor, sweeping hair, when a new line called Bumble and Bumble came in and she thought the packaging and messaging was the coolest thing she'd ever seen.
That moment launched a career scaling brands from under $10 million to over $100 million.
The hard part was never the product.
It was knowing when to stop protecting what was built and start being honest about what needed to change.
Her take on where most brands get stuck: they get really good at one channel, Amazon, DTC, or retail, and struggle to make the jump to the next.
The brands that break through aren't necessarily the ones with the best product. Everyone has good products now.
What separates them is whether consumers see the brand as part of their lifestyle, not just something on a shelf.
Her advice to founders stuck between $5 million and $20 million comes down to one question:
What is your customer's experience like right now?
The longer you're in business, the easier it is to see your brand through internal eyes instead of customer eyes.
That's when growth stalls.
The brands that reach the next level are willing to challenge their assumptions, stay aligned with what the brand stands for, and adapt before the market forces them to.
They stay honest about what's working, what's not, and what needs to change.
"The brand is the most important thing. Everything you put out into the universe has to align with your three pillars. And if it doesn't serve you, cut bait and move on." - Brianne Price, CPG Executive and Chief Revenue Officer
Brianne didn't get into consumer brands from a business school case study.
She got in from a salon floor, sweeping hair, when a new line called Bumble and Bumble came in and she thought the packaging and messaging was the coolest thing she'd ever seen.
That moment launched a career scaling brands from under $10 million to over $100 million.
The hard part was never the product.
It was knowing when to stop protecting what was built and start being honest about what needed to change.
Her take on where most brands get stuck: they get really good at one channel, Amazon, DTC, or retail, and struggle to make the jump to the next.
The brands that break through aren't necessarily the ones with the best product. Everyone has good products now.
What separates them is whether consumers see the brand as part of their lifestyle, not just something on a shelf.
Her advice to founders stuck between $5 million and $20 million comes down to one question:
What is your customer's experience like right now?
The longer you're in business, the easier it is to see your brand through internal eyes instead of customer eyes.
That's when growth stalls.
The brands that reach the next level are willing to challenge their assumptions, stay aligned with what the brand stands for, and adapt before the market forces them to.
They stay honest about what's working, what's not, and what needs to change.
"A lobster knows when it's time to shed its shell when it starts getting uncomfortable. If it never felt uncomfortable, it would never grow." - Ari Barmapov, Co-founder of Foundations
Ari didn't start in a boardroom. He started at Blockbuster, selling membership add-ons from behind a cash register, just asking everyone who walked in.
The more he asked, the better he got, and he ended up the top salesperson in the entire district.
That was the whole formula, and it hasn't changed since.
No auto-dialer, no real CRM. Just a phone, a phone book, and 150 to 200 manual dials a day.
Brutal reps, but invaluable ones.
Four President's Clubs later, he built Foundations to give founders what nobody gave him.
His take on why founders stay stuck in founder sales: they try to delegate before they've done the work themselves.
BDRs aren't there to figure out your business, and a VP of Sales isn't going to cold call for you.
The only way out of founder sales is through it.
Do it yourself, do it a hundred times, know what works, then pass it on.
On cold calling being dead: it isn't.
People say it's dead because you can't sell a $99 course on it.
You actually have to pick up the phone, and most reps today won't sit down and make focused calls for 90 minutes.
Not because they don't have the time, but because they don't want to be uncomfortable.
That discomfort is the whole point.
The one question he leaves every founder with: when was the last time you booked a meeting with someone you didn't know?
If you can't remember, you already know what to do next.
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