A portfolio company came to us last year with 37 quota-carrying reps and a plan to hire 20 more. They had the white space mapped, the budget approved, and a buyer base they’d already proven they could sell to. What they didn’t have was an enablement function, a training program, or any answer for why their win rate was stuck at 8%. They weren’t about to scale a sales team. They were about to scale dysfunction. The PE firm that owned them failed to see it because no one on their team had ever carried a quota.

I’ve been working with PE-backed companies on sales execution for well over a decade. The mistakes haven’t changed. The reason is structural: most PE firms are staffed with finance people. They know how to buy a company, scale it on paper, and sell it. They don’t know how to assess sales capability, and most don’t have anyone on the team who has actually carried a quota. So when revenue stalls at a portco, the firm reaches for the only playbook it knows: hire faster, push harder, demand more pipeline. The motion is wrong. The sequence is worse.

Here are the five mistakes I see PE firms make again and again, and what to do instead.

1. Treating Sales as a Headcount Problem

The fastest way to burn cash is to hire more reps before fixing the underlying sales motion. If your win rate is 8% and your average deal velocity is nine months, adding headcount just scales dysfunction. You haven’t built a sales team. You’ve funded an expensive education in what not to do.

That 37-rep portco is a good example. Their first ask was simple: help us hire the 20. We pushed back. Adding headcount into a broken system doesn’t fix the system. It scales it. Before any new hires came in the door, we resequenced the work. We mapped each existing role against actual white space, not assumed white space, actual territory coverage and buyer capacity. We rewrote the role definitions and the performance expectations that came with them. Most importantly, we built an enablement function and a learning management system from scratch. Neither had existed before. You can’t hold reps accountable to a standard you haven’t built.

Then, and only then, we helped them hire the 20. Those reps walked into a structured training program. They had answers to their questions instead of having to dig through a CRM hoping something useful would surface. The result: even on a complex SaaS product, the new hires are closing their first deal in week four or five.

That outcome is not accidental. It’s what happens when the infrastructure exists before the headcount arrives.

That’s the difference. And here’s the truth everyone knows but no one wants to say out loud: when you hire people without giving them what they need to succeed, you haven’t just wasted a hire, you’ve stolen quarters from your portco. Quarters they could have used to grow. There’s a moral imperative in making a new hire. If we offer somebody a job, we ought to have the training and the capability to coach them up so they can become successful in that job. Hiring is the slowest thing we do. Multiply one wrong hire by twenty and you’ve created a problem you’ll spend quarters cleaning up. Not weeks. Not months. Quarters.

2. Doing Comp Before Quotas and Territories

Operating partners call us all the time and say, “we need to revise the comp plan.” That’s almost never the right place to start.

Comp, quotas, and territories are linked and the sequence matters. You cannot build a comp plan without knowing the quotas. You cannot build the quotas without knowing the territories. And you cannot draw the territories without knowing where the white space actually is. Skip a step and you’re paying people based on assumptions stacked on top of assumptions.

The sequence is not negotiable: territories first. Map where a rep can find a number. Quotas second. Ground every quota in the white space the territory can yield. Comp third. Build the plan against quotas you can defend.

Reverse it and the damage compounds fast. Reps end up with impossible quotas, working underbuilt territories, paid against a plan that was never grounded on reality. They figure it out by April. Then they go home, tell their spouse the math doesn’t work, and start interviewing somewhere else. Your best people leave first. They always do.

3. Buying Tools Before You’ve Nailed the Pitch

Every week there’s a new platform. Gong, Outreach, ZoomInfo, Salesforce, pick your favorite AI-powered seller. Some sexy salesperson gets hold of a chief of staff or a head of revenue and convinces them the next tool will fix the funnel.

It won’t. Not because the tools are bad. Some of them are genuinely useful. But if you haven’t nailed the pitch, none of the tooling matters. The pitch is what you say, who you say it to, and the context you’re saying it in. Get that wrong and the tools just give you faster, sharper ways to deliver the wrong message. It’s like having a Ferrari in the garage but you don’t have any car keys. The capability is there. The execution isn’t.

Most PE-backed sales orgs end up running a Frankenstein’s monster. The tech stack the company had when it was acquired is too expensive to replace. The tools the new operating partner brought in don’t talk to it. Salesforce is the system of record but half the workflow lives in a different platform and nobody’s sure why. The tools were supposed to help your team execute the sales process more effectively. Instead, the tools just give them more ways to execute the wrong strategy efficiently.

This is not a technology problem. It’s a sequencing problem.

Fix the pitch. Fix the buyer profile. Then go shopping.

4. Treating All Revenue as Equal

Bookings are bookings, right? Wrong. Bad-fit deals don’t just churn faster. They actively erode the standards your sales team is supposed to operate under.

Here’s the mechanism. Sales reps are single-threaded in pursuit of the goal. So one rep, on the edge of a quarter, takes a deal that doesn’t fit your ICP. Maybe the geography’s wrong, maybe the size doesn’t match, maybe the SLA terms required a special exception. The deal closes. Bookings are bookings.

Then, two weeks later, another rep on the team brings you a deal that looks just like the first one, and asks for the same exception. “You let Jim sell that deal. Why can’t I sell this one?” You say no. Then a third rep comes with a similar request. Then a fourth. Each of them points to the precedent. And they’re not wrong; the precedent exists.

This is how it works: your standards no longer remain standards. They become merely suggestions for the type of client you should sell to. And the faster you’re growing, the worse it gets. That’s exactly when deals are coming thick and fast and the deal-review process is the first thing to fall apart.

The fix isn’t a comp lever. The fix is a process. Before any non-standard deal is accepted, somebody who knows the company and isn’t measured on bookings, usually an operations leader, looks at the price, the terms, and the customer fit. If it doesn’t meet the standard, it doesn’t close. That’s the only way to keep your ICP from being rewritten deal by deal, exception by exception.

5. Benching the Founder Too Early

Founders are often the best closers in the early market. They have conviction, deep product knowledge, and the kind of customer empathy that hired sales leaders can’t fake. But every founder CEO eventually faces the moment when the company has grown past their ability to know everything that’s happening across every department. That’s when the founder needs to step back. Not before.

Here’s the signal to watch for: when the founder believes the answer to every problem is for them to get personally involved, they’ve stopped being a CEO and started being a fill-in-the-blank for whatever role isn’t working that week. A founder who started by selling every deal will instinctively parachute back into sales the moment something stalls. That motion was right when they were a team of one. It becomes a liability when they have a professional sales organization that has to learn to run without them.

Pull the founder out before that moment, though, and you’re trading momentum for “professionalism” you haven’t earned yet. There’s no replacement for founder conviction in the early market. Take that away before there’s a documented, repeatable motion someone else can run, and revenue stalls fast.

The consequences of getting this wrong aren’t theoretical. Twice in the last decade, I’ve watched a portco get written off entirely by the PE firm and acquired by a competitor for pennies on the dollar. The product wasn’t broken. The team wasn’t unfixable. They attacked the problems in the wrong order, ran out of runway, and the investment thesis collapsed. PE firms don’t like to talk about those write-downs. But a lot of the reasons those investments fail come back to the same root issue: the sequence in which they tried to fix what was broken.

The Fix Is the Sequence

Nail the pitch. Prove the process. Then scale the machine.

That’s the order. There is no shortcut.

When an operating partner tells me, “we can’t afford to wait, we need pipeline and headcount now,” my answer is the same every time. You can either do it correctly now or you’ll do it correctly in FY27. The choice isn’t between fast and slow. It’s between the path you take and the year you take it in. Compress the sequence and the math catches up with you anyway. Hire before training. Ship comp before quotas. Buy tools before you’ve fixed the pitch. You’ll churn through people, burn through quarters, and end up doing the work later, with less runway, and with an investment thesis that’s running out of room.

Get the sequence right, and sales becomes exactly as the growth engine the deal model assumed it would be. Get it wrong, and you’ve funded an expensive education in what not to do.

What to Do Monday Morning

If you’re a PE operating partner reading this, here’s where to start.

Forward this article to two or three of your portfolio CEOs. Don’t frame it. Ask them what they think. Bring it up on the next one-on-one.

Watch what comes back. The CEOs who reply with three things they want to start fixing. Those are the portcos ready to do the work. The CEOs who tell you it makes sense and they’ve got it handled? Those are the ones who will show you, in FY27, that they didn’t.

Either way, you’ll know more on Tuesday than you did on Monday. In this business, that’s the whole game. Start there.