Sales Leadership Training

Most CROs Manage Reps Wrong (CRO at $4B Tech Company)

January 16, 20263 min read

Most CROs beat up reps for pipeline.

Jeff Ford doesn't.

He's the CRO at Trimble (a $4B+ tech company). And he's built high-performing teams at multiple billion-dollar organizations by managing reps completely differently than everyone else.

Here's what he does that most sales leaders get wrong.

Don't beat up reps for pipeline. You'll get pipeline that won't convert.

Jeff's seen it over and over. CROs set 3x or 4x pipeline targets. They come hell or high water to hit that number. They beat up reps to achieve it.

And they get exactly what they asked for.

Pipeline that doesn't convert.

"Pipeline increased, but conversion rates dropped. You're wasting time, wasting sales cycles, wasting the most precious resource anybody has—time."

Jeff holds managers accountable for pipeline amounts. But he treats it as a coaching mechanism for reps, not a whip to crack.

Every customer-facing role has a pipeline target. Including customer success.

If you're interfacing with customers, you're getting insights. You're spotting opportunities.

Customer success pipeline often converts at 50%+.

"You're leaving a lot on the table if you're not looking at pipeline across every role that talks to a customer."

Jeff assigns pipeline targets to every single customer-facing role in his org. SDRs. AEs. Customer success. Everyone.

He doesn't manage reps to quota. He manages them to their personal earnings goal.

Here's where Jeff blew my mind.

Every sales org he runs, he builds earnings calculators. Simple spreadsheet. Single variable input at the top: "What do you want to make?"

Then he manages them to THAT number. Not their quota.

"If you want to make $500,000 this year and your OTE is $300,000, I'm going to manage you to your $500,000 and be your accountability partner to help you get there."

The data backs this up.

90% of reps pick something NORTH of their OTE. Only 5% pick their OTE. And 5% pick something lower (which raises the question: are they the right person in the right seat?).

Jeff digs into the WHY behind the number. Kids going to college. Aging parents moving in. Buying a vacation house. Saving for a new car.

When reps are emotionally attached to their goal, they show up differently.

He studied 300% Club achievers. They all did the same thing.

Jeff ran a study at Informatica of reps who consistently hit 300% of quota year after year.

The answer? Surprisingly simple.

Every one of them was focused on hitting 300%. They broke it down into quarterly, monthly, weekly, and daily goals.

One rep's favorite story: He had to hit $50,000 of pipeline per day. Every night at dinner, his wife asked "How did your day go?" His answer depended on whether he hit his pipeline target.

"If I hit $70,000, it was great. If I didn't, here's what I think we can do better tomorrow."

That's how specific and programmatic top performers are.

AI is the productivity unlock. Not more headcount.

Jeff thinks about growth in three ways:

1. Productivity (higher output from existing reps)

2. Product (new products or new markets)

3. Capacity (adding reps—the most expensive way)

This year, AI is the key to unlocking productivity gains. Not 3-5% marginal improvements. Real step-change increases of 10-30%+.

"Sales reps are terrible at data entry. If you give me something that can listen to my conversations and automatically put information in, I get better data AND it saves me time to run 4-5-10 more opportunities per quarter."

Jeff's leaning into agentic AI: tools that auto-fill CRM from call recordings, provide sentiment scores in real-time, help with account research and pitch decks.

"If we're not helping drive productivity up, finance is going to ask: Why am I adding capacity when 70% of your sellers are short of their number?"

Bottom line:

Stop managing reps to quota. Manage them to what they actually want to earn.

Build earnings calculators. Break goals into daily targets. Assign pipeline to every customer-facing role.

And lean into AI or you'll be asked about it when you're flatfooted.

Your move.

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