6 Billing Red Flags That Signal Trouble for Subcontractors

When people think about construction challenges, they usually picture jobsite stuff: weather delays, safety incidents, material and labor shortages—or big-picture stuff like market uncertainty and industry outlook. All real. All painful.

But here’s the dirty little secret: the biggest red flags for subcontractors don’t show up on the jobsite. They’re buried in the back office—in billing, invoicing, and cash flow.

I recall talking to a controller at a drywall subcontracting business owner at a conference earlier this year. He told me flat out: “I lose more sleep over billing than I do over labor.” That stuck with me. Because when the back office slips, everything downstream—cash flow, payroll, growth—starts to wobble.

Let’s talk about six of the most common billing red flags subs face and how to get ahead of them.

1. Slow or Late Payments

Everyone’s got a story here. One that’s etched into my memory is when I spoke with a PM at that same conference in Idaho who said he once waited over 90 days for payment on a job that was already completed and signed off. He said, “It’s like we were financing their project, interest-free. Last time I checked, I wasn’t a bank, and if I was, interest-free wouldn’t be my model!”

The risk: Slow payments crush cash flow and force you to bankroll projects long after the work is done. In fact, subcontractors tapping into retirement savings to cover business expenses has increased by 147% since 2019.

How Siteline helps: Siteline automates billing and lien waivers, and keeps polite-but-persistent reminders flowing until you get paid. On average, subs using Siteline cut payment delays by three weeks. That’s payroll you don’t have to float.

2. Billing Errors That Kill Momentum

A friend at a construction site service company still cringes telling this story: they missed a waiver in a billing package, and the GC rejected the entire pay app. That little mistake cost them a full month of cash flow. This is just one instance, by the way. For a full list of billing errors that can invalidate your pay apps and push payment out further, check out this article.

The risk: Even the smallest errors—like a missing waiver or typo—can delay approvals, stall cash flow for 30-plus days, and hurt your credibility with the GC.

How Siteline helps: Siteline generates GC-specific pay apps, validates waivers, and even double-checks dates and amounts with artificial intelligence. Think of it as your built-in proofreader—no red pen necessary.

3. Billing Deadlines That Sneak Up on You

Billing cutoffs and lien notice dates aren’t exactly forgiving. Miss one, and you’ve just bought yourself another 30 days. Worse yet, you’ve waived your right to payment entirely.
Early in my career at Siteline, I remember visiting a sub in Arizona, who’s a customer now, but shared a story from a couple of years ago when she kept all deadlines in a color-coded spreadsheet. She got sick for a week and missed a couple of cutoffs that resulted in roughly $200k in delayed cash flow. That’s a huge deal.

The risk: Critical billing deadlines are easy to miss, and the consequences can be devastating: delayed cash flow or even losing your right to payment.

How Siteline helps: Siteline tracks all critical deadlines, including billing cutoffs. It sends alerts so you don’t rely on memory or a rainbow-colored Excel file. (Although pretty, I’d still argue the Siteline interface looks nicer!)

4. The Change Order Black Hole

Change orders are notorious for vanishing. And they aren’t small potatoes. In fact, change order costs can represent 10-15% of the contract value. I’ve heard stories about CORs sitting in email drafts for months, where no one knew what was approved, what wasn’t, or where the paperwork lived. Then, by the time accounting followed up, half the details were gone. No tracing, no accountability, and finger-pointing doesn’t help money come in the door.

The risk: Lost or untracked CORs = lost revenue and disputes.

How Siteline helps: Siteline syncs CORs with your ERP and shows you every status in real time. Pending, approved, disputed; it’s all there. No more “email archeology.” 

5. Flying Blind on Cash Flow

Subs typically don’t fail because of bad work; they fail because they run out of cash. In fact, 59% of subcontractors admit they don’t prepare for cash needs ahead of time—so when expenses hit, they’re scrambling. I heard from a concrete sub whose grasp on cash flow was anything but concrete before Siteline. Their system was a whiteboard and a gut feeling. Which sort of works … until it doesn’t. And by that time, it could be too late.

The risk: Without visibility, every decision (hiring, bidding, buying equipment) feels like rolling the dice. And let’s face it, you don’t want to take any unnecessary gambles with your business.

How Siteline helps: Siteline delivers real-time billing and cash forecasts as well as A/R aging reports. You go from guessing to planning, and that’s the difference between barely surviving and strategically growing.

6. Teams Working in Silos

The old blame game is universal—and it's a game no one ever wins at. Finance blames PMs. PMs blame accounting. Field crews shrug and say, “Ask the office.” Meanwhile, your cash is stuck in limbo.

I was on the phone with a large fire protection company that told me this exact story. Before Siteline, siloed teams weren’t just slowing payments—they were hurting their cash flow, bottom line, and even their company culture.

The risk: Siloed teams create finger-pointing, delays, and frustration that eat into both profits and morale.

How Siteline helps: Siteline centralizes everything—billing, waivers, compliance—in one, easy-to-use system. Everyone sees the same truth in real time. That means less confusion, fewer excuses, more control, and yes, even a stronger company culture.

From Red Flags to Green Lights

Here’s the thing: you can’t control the rain. (Though scientists are trying!) You can’t control material prices. But you can control billing errors, missed deadlines, and compliance chaos.

And that’s exactly what Siteline helps subcontractors do.

Construction is risky enough; why let your back office add to the pile? But don’t just take my word on it. I’ll leave with you a final quote from Kiera V., the Contracts Administration Manager at FireTron, Inc.: “If you’re thinking about Siteline, you should have already done it.”