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People, Systems, Deals

March 25, 2026 · 4 min read · Chris Smith

Every company I’ve worked inside had the same problem at some point: something was broken and nobody could agree on what it was.

At WeWork, we’d miss a quarter and the conversation would immediately jump to pricing or lead volume. But half the time the real issue was a regional manager who couldn’t coach reps, or a handoff between marketing and sales that nobody owned. The revenue problem was real, but the cause was somewhere else entirely.

I saw this enough times across enough companies that I started sorting every growth problem into one of three buckets: People, Systems, Deals.

People is who you have and how they’re organized. Do you have the right person in the role? Do they know what’s expected of them? Does the org structure make sense for how work actually flows, or did it just accumulate over time?

Systems is the processes and tools that connect work across people. How does a lead become a customer? What happens after they sign? Who owns the handoff between marketing, sales, and customer success? Is any of this documented, or does it live in one person’s head?

Deals is the revenue engine itself. Pipeline volume, conversion rates, average deal size, sales cycle length, churn. The numbers that tell you whether the machine is working.

These three categories aren’t independent. They compound each other. Great people working inside broken systems will burn out and leave. Good systems staffed by the wrong people produce mediocre results efficiently. And no amount of deal-making overcomes an org that can’t deliver on what it sells.

Where this came from

At WeWork, I watched all three break simultaneously during hypergrowth. We were hiring so fast that managers had eight direct reports before they’d finished onboarding themselves. The CRM was a graveyard. Pipeline reviews were a performance rather than a diagnostic. Every quarter, leadership would focus on Deals (more logos, bigger contracts) when the bottleneck was usually People (undertrained managers) or Systems (no lead routing, no handoff process, no renewal workflow).

At CloudKitchens, I had to build all three from scratch in 8 months. Forty-two people, nine markets, zero playbook. The sequence mattered. I built the systems first (market launch process, CRM configuration, comp plan), then hired people into those systems, then turned on the revenue engine. We hit 120%+ of plan. The region that launched without the systems in place took 40% longer to reach the same revenue targets.

At Apple, the systems were world-class. Retail operations ran like clockwork. But the people challenges were constant: matching specialists to the right customer segments, coaching through a product lineup that changed every quarter, keeping top performers engaged when the career path was narrow. Even with great systems, the People bucket demanded attention every week.

How to use this

When something feels broken in your company, pause before you react. Ask which bucket the problem is actually in.

Revenue is down. Is it a Deals problem (pricing, market, competition)? A Systems problem (leads aren’t getting to reps, reps don’t have a playbook, there’s no follow-up process)? Or a People problem (wrong hire, missing role, burned-out manager)?

The diagnosis changes the fix completely.

Most founders default to Deals. Revenue is the most visible metric, so it gets the most attention. But in my experience, the majority of revenue problems at scaling companies trace back to People or Systems. The revenue number is a symptom. The cause is upstream.

Common mistakes I see

Hiring a VP of Sales when you don’t have a pipeline. That’s a People investment when the bottleneck is Systems. The VP shows up, asks “where are the leads?” and you’re both stuck.

Building a CRM when you don’t have reps. That’s a Systems investment when the bottleneck is People. You’ll configure it for a workflow that doesn’t exist yet, then reconfigure it six months later.

Discounting to close more deals when your close rate is fine but lead volume is low. That’s a Deals fix for a Systems problem. You’re leaving margin on the table to solve the wrong issue.

Before you commit budget, headcount, or your own time, figure out which bucket you’re actually solving for. Then spend accordingly.

TL;DR — The Bottom Line

This framework isn’t original. Any operator who’s scaled a company will recognize these categories, even if they use different names. The value isn’t in the labels. It’s in the discipline of diagnosing before prescribing.

When something breaks, ask: People, Systems, or Deals? Start there.

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