Sales isn't always a straight line.
We all know that sales sometimes is like going into a maze with a blindfold and hoping we find the exit at some point.
Now, add on scaling a sales team without the right support? That's a whole different ball game.
I'm about to tell you a story that'll make you rethink everything you know about scaling a sales team.
Meet Sam Jacobs, a guy who learned some of his biggest lessons by completely striking out.
Personally, I learned more in this podcast episode than anything else I have listened to or read.
Seriously, grab a notepad for this one and take notes.
You'll want to remember this and absorb this information multiple times.
Let's dig in.
Check out my interview with Sam
The setup that looked perfect (but wasn't)
Here's how Sam's story starts.
He gets recruited to a company with thousands of leads, impressive enterprise logos, and what seems like unlimited potential.
When he joined this company, everything looked incredible on the surface.
Tons of inbound interest. Big-name customers like NASDAQ.
A platform everyone seemed to know about.
Sounds like a sales dream, right?
How could he possibly have a problem in this scenario?
Well, this is what Sam said in the interview that blew my mind about why it actually wasn't the perfect scenario.
"I walked in thinking we had it all," Sam told me. "Thousands of leads coming in monthly, brand recognition most startups would kill for, and some seriously impressive logos. It felt like printing money was just around the corner."
But the twist? Not all leads are created equal.
The harsh reality check
As Sam dug deeper into the issues, he realized that just because people know about your product doesn't mean they want to buy it.
In fact, sometimes brand recognition can be deceiving.
"We had tons of casual users who'd sign up for a month, stream their kid's baseball game or their company's annual meeting, and then disappear," Sam explained. "These weren't leads - they were drive-by customers who never intended to stick around."
The data can either paint a beautiful or painful story.
The numbers told a painful story in this scenario.
Most users would sign up for monthly plans, use the platform for a single event, and then immediately cancel.
The free player with their company logo was generating what looked like leads, but they were just digital tourists with no intention of becoming permanent residents.
Huge problem that he needed to solve if the team was going to get any traction.
The technical nightmare nobody warned him about
Here's where things got complicated real quick.
Live streaming sounds simple on paper.
Point a camera, hit broadcast, and you're good to go, right?
Wrong.
Sam discovered a mountain of technical barriers nobody had bothered to mention during the recruitment process. "We're talking about needing massive bandwidth - like 100 up/100 down internet speeds," he said. "Try finding that at your average conference venue or corporate office in 2015."
The reality was brutal:
Most locations physically couldn't support true live streaming.
It'd be like trying to run a Formula 1 race on a dirt road.
I would not recommend this unless you like being stuck and stressed out.
Which is exactly what was happening with Sam’s team.
The leadership mistakes that kept him up at night
Looking back, Sam's brutally honest about his mistakes.
He did what most ambitious sales leaders would do:
- Hired aggressively
- Assumed past success would guarantee future growth
- Tried to force a sales motion that just didn't match the product
"I brought my entire playbook from previous wins," Sam admitted. "But it was like trying to use a football strategy in a basketball game. Different sport, different rules, different everything."
Read that quote again, just because you won with one playbook doesn't mean that same playbook will work everywhere else.
Take plays from the playbook, but the entire playbook might not work.
The culture clash nobody saw coming
But here's the real kicker.
The internal culture was rejecting anything sales-related.
The founders were deeply skeptical of sales, the support teams actively resented the sales team, and nobody truly believed in the approach.
Sounds like the most fun sales team to build, right?
Sam tried everything to inject some life into the situation.
He brought in sales gamification platforms, added celebratory air horns for new opportunities (I love these, by the way), and created high-energy sales rituals.
"I must have looked insane," he laughs now. "Here I was with my rah-rah sales culture in a company that saw sales as a necessary evil at best."
As you can see, these two worlds just don't mix.
Before joining a company, make sure the founders actually believe in sales. Otherwise, you're in for an uphill battle.
The marketing wake-up call
Here's where Sam's story takes an unexpected turn.
He realized something that completely changed his approach to sales leadership:
Marketing isn't just important - it's everything.
"I had it backward," he told me. "I thought great salespeople could overcome any obstacle. But the reality is, you need three things in this order: an exceptional product, a compelling marketing message, and only then a sales process."
When you join a company, make sure all three are checked off.
If not, reconsider joining it.
The Pavilion transformation
Today, Sam leads Pavilion with a completely different approach.
Instead of rushing to scale, he's focused on building relationships that last.
"At my old company, I was trying to sprint a marathon," he explains. "Now I'm playing a completely different game. It's not about quick wins - it's about building something that lasts."
His approach now?
Build relationships before you need them. Give value before you ask for anything. Play the long game.
Simple rules to follow for anyone looking to win long term.
The real truth about sales leadership
Success in sales isn't about how fast you can run.
It's about choosing the right path and staying committed.
"The most valuable skill isn't closing techniques or pipeline management," Sam reflects. "It's patience. Understanding. Strategic thinking. And most importantly - knowing when the market is trying to tell you something."
Are you ready to rethink your entire sales approach?
The maze isn't about finding the fastest route. It's about understanding every twist and turn.
Want to hear more raw stories about sales leadership?
Check out my full conversation with Sam, where we dive even deeper into these lessons and more on Revenue Rebels On the Record.
