Most founders don't figure this out until a client churns, a product feature flops, or a deal falls apart at the finish line.
Then they ask themselves: "What went wrong?"
The answer is almost never what they expect.
It's not the product. It's not the market. It's not the pricing.
It's the hiring.
More specifically, it's hiring people who can only see ONE side of your business.
I've watched early-stage founders make this mistake over and over.
They bring on talented, sharp, impressive people... who end up building things customers don't want, or closing deals the team can't actually deliver.
The result?
Revenue leaks everywhere.
And nobody can explain why.
Here's what's actually happening.
THE PROBLEM WITH HOW STARTUPS HIRE
When you're building a marketplace business (or really, ANY business that serves two groups of people at once), single-sided thinking is a silent killer.
Think about your business for a second.
You've got:
Buyers (clients, end users, customers)
Suppliers (employees, service providers, internal teams)
Every decision your team makes touches BOTH sides
Every feature
Every process
Every policy
Every hire
When someone on your team only thinks about one side?
You create friction. You create leakage.
You create the kind of slow revenue bleed that's really hard to diagnose.
I call this the marketplace mindset gap.
And it's one of the biggest hiring mistakes founders make when building revenue teams.
WHAT AIRBNB FIGURED OUT EARLY
Let me tell you about a company that turned this exact idea into a $75 billion business.
Airbnb.
They could have hired the obvious way. "Find people who love travel. Find people passionate about hospitality."
That would have been fine.
And totally wrong.
Instead, they built their hiring culture around one question: Can this person think about two customers at once?
Not the guest OR the host. The guest AND the host.
Their user-centered approach became one of the most studied in the industry.
Not because they had a design team full of geniuses, but because every person they brought on, across every function, was wired to ask: "
How does this affect the host?
How does it affect the guest?"
That thinking showed up everywhere.
In the product. In support. In onboarding. In marketing.
And when Airbnb pushed aggressively into new business areas, they took the same hiring philosophy with them.
People who understood that you can't win on one side of a marketplace without winning on both.
Hosts kept listing.
Guests kept booking.
Revenue compounded.
That's not a coincidence.
WHY SINGLE SIDED HIRING IS SO EXPENSIVE
Let's talk numbers.
Because founders consistently underestimate the real cost of this mistake.
When you hire someone who only thinks about ONE side of your business:
Sales reps overpromise because they're focused on closing, not on what delivery actually requires
Product teams build for the loudest customer voice without thinking about the operational impact
Customer success burns out cleaning up messes that could have been avoided upstream
Your best clients leave not because of price, but because the experience felt inconsistent
A bad hire in a key revenue role can cost you 3x their annual salary when you factor in recruiting, ramp time, client churn, and team morale.
That's not a rounding error, that's real money for a startup running lean.
What to look for instead
Stop hiring for skill alone, start hiring for HOW someone thinks.
The question that separates average candidates from marketplace thinkers is this:
"Tell me about a time you solved a problem for one group, then stopped to ask who else that decision would affect."
Watch what happens.
Some candidates freeze. They've genuinely never thought that way.
Others light up.
They walk you through a story where they proactively looped in another stakeholder, another team, another user... before shipping, before deciding, before moving forward.
THAT'S the person you want on your revenue team.
Because that person builds things that don't break on the other side of the transaction.
They close deals that operations can actually deliver, they think in systems, not silos.
A simple framework to start using TODAY
You don't need to redo your entire hiring process.
You just need to add ONE filter.
During screening
Ask candidates to describe their previous role's customers. Then ask: "Who else depended on the work you did?" If they can only name one group, take note.
During the role-specific interview
Give them a scenario. "We're changing our onboarding process. Walk me through how you'd think about the impact." Listen for whether they bring up multiple stakeholders without being prompted.
During reference checks
Ask former managers: "Did this person ever flag unintended consequences before a decision was made?" That answer tells you everything.
It's a simple filter.
But it's remarkably effective.
This kind of multi-stakeholder thinking is becoming the baseline for the best companies in the world.
Even platforms like Picsart's new AI agent marketplace are built around the idea that both creators AND their audiences have to win for the platform to grow. The best teams think that way by default.
Here's what happens when you hire even ONE person with a marketplace mindset.
They start asking questions nobody asked before.
If we offer this discount, what does that signal to existing clients?
If we speed up this process for buyers, does it create pressure on the supplier side?
Who else is affected by this decision?
Those questions feel small in the moment, they're not.
They're the difference between a business that compounds and one that constantly patches leaks.
Your team starts thinking end-to-end.
Your product stops breaking on one side while winning on the other.
Your clients stay longer because the experience holds up all the way through.
That's how Airbnb turned two-sided thinking into one of the most durable revenue engines in modern business.
That's how YOU can do it, even at 10 or 15 people.
OVER TO YOU
Building a great revenue team isn't about finding the smartest people in the room.
It's about finding people with the right mental model.
The ones who zoom out naturally and the ones who ask "who else is affected?" before anyone has to remind them.
Those people exist.
You just have to know what question to ask.
Hire for marketplace mindset.
The rest will follow.