Common Billing Challenges in Business

Billing Problems Sometimes I get drawn into billing disputes. Sometimes there is the written word in a contract that is cited, other instances “fairness” is invoked. I like the one way street of “fairness” as it lies squarely in the eye of the beholder, it can lead to fun conversations. The person who sees no grey and becomes the Pharisee of the interpretation of words is the most difficult to deal with, in the most general terms. However, most disputes today flow back to my grocery store of LTL analogy. Shipper puts wrong weight, wrong description, wrong cube and so forth on the BOL and carrier finds otherwise. Always after the fact, the modified bill with higher charges finds its way to the customer and the cycle of anger begins. What needs to happen in the future is real time updates of dimensions, and/or updated accessorials if appropriate to give the shipper/3pl/consignee a heads up that something changed and why it changed. That way their system can be updated if they agree with the correction and things flow smoother on most situations. Disagreements can be resolved sooner than 60 days later when balance dues get sent after being paid short. Our industry spends way too much time and money on the backend collecting and paying of freight bills. I am not saying it isn’t needed because Mastio results tell us that all carriers don’t do the best job of invoicing correctly but we need to drive out this cost of the supply chain as much as possible through proactive communication, which generally doesn’t happen. I am in favor of eliminating some time based accessorials like inside delivery for example by evaluating stop times and if less than 20 minutes, remove the fee, or better yet, don’t add the charge at all. Open to suggestions to make this better.

In my recent LinkedIn poll, “invoice confusion” emerged as the second highest source of friction between #3PL warehouses and their clients. So drilling down on this one, I know this can significantly impact client relationships, not to mention profitability. I had one client whose 3PL had a charge each month for a line item called "Joe". It ranged from $300 to $4000 at times and there was no other explanation. I'd be annoyed too if I were the brand. I mean, what could Joe be doing all month? How should a 3PL mitigate this?? Some of the problems I've seen - 😡 Complex Rate Structure 3PLs often juggle multiple pricing models, client-specific rates, volume discounts, and seasonal charges, creating ample room for misunderstandings and errors. 😡 Data Quality Manual data entry processes can lead to problems. Missing charges, incorrect quantities, and mismatched service dates not only impact revenue but also erode client trust. 😡 Lack of Transparency Clients often struggle to understand the breakdown of charges on their invoices. Without clear explanations of services rendered and associated costs, misunderstandings can quickly escalate into disputes. 😡 System Integration Gaps. Many 3PLs face challenges in synchronizing their #WMS with accounting platforms. This can lead to delayed billing cycles and missed billable activities. 😡 Inaccurate Billing Data Errors in data entry can result in inaccurate charges, leading to customer complaints and potential revenue loss. These inaccuracies can also disrupt cash flow by affecting timely payment collection. Strategies to Mitigate Confusion 🟢 Implement Automated Billing Systems Automation is key to reducing errors and improving billing accuracy. 🟢 Standardize Rate Cards Build consistent pricing structures while allowing for custom client arrangements. Streamline billing processes without sacrificing flexibility for key accounts. 🟢 Enhance Data Collection Use your WMS to automatically track all billable activities. This eliminates manual tracking and ensures every service is captured, from storage to special handling. 🟢 Provide Detailed Activity Reports Break down complex charges and provide supporting data to prevent disputes and enhance transparency. 🟢 Real-Time Data and Analytics This enables quicker response times to changes and enhances overall operational efficiency. 🟢 Customize Billing Profiles Tailor billing profiles to align with client-specific pricing agreements and billing rules. Invoice confusion remains a significant challenge in the 3PL industry, but it’s not insurmountable. Remember, the goal is not just to minimize errors but to build trust and strengthen client relationships. A clear, accurate, and timely invoicing process demonstrates professionalism and reliability, key factors in client retention and business growth in the competitive 3PL landscape. For my 3PL friends, what is the fix you have put in for this?

People overcomplicate billing systems. And when billing breaks down, trust disappears fast. A few weeks ago, I spoke with a new client who had just lost their biggest customer. Not because of poor service. Not because of pricing. But because of a billing error that went unnoticed for weeks. They didn’t just lose one client — they lost the referrals that would’ve come from that relationship. All from one small, avoidable mistake. If you’re a growing business owner, here’s what you need to know: Avoid: ❌ Chasing clients for payments manually ❌ Letting write-offs slip through the cracks ❌ Delaying invoices “until you have time” Instead: ✅ Automate invoicing and reminders ✅ Track time and expenses in real-time ✅ Reconcile monthly, not yearly Focus on this for the first 30 days. Build from there. Simple systems prevent expensive mistakes. And your reputation deserves that kind of protection. 👉 Make one change this week: automate just one part of your invoicing process. It’s a small move that builds long-term trust with every client you serve. You’ve worked too hard to let billing errors undo your momentum. And, your business and those who need you are depending on it. If this post hit the spot, please share! ♻️

When you start a new job, the first 90 days are all about learning and finding a few quick wins. At Gorgias, there were plenty of areas to tackle, but according to our CEO, priority one was untangling our finance mess. I started by speaking to stakeholders and listening. The more stones I turned over, the more problems I found. I quickly realized there were no "quick wins" here—just a complete overhaul. So, I opened Notion, documented every issue, stack-ranked them by priority, and got to work. After tackling some immediate fixes, I naively turned my attention to payment processing fees. With 10,000 customers (at that time)—98% of whom paid by credit card—this seemed like a rock-solid initiative. While on the surface, lowering Stripe’s 2.9% rate looked like an easy way to save the company hundreds of thousands of dollars annually, what I didn’t anticipate was being thwarted by the tangled mess of our in-house billing platform on Stripe. Originally built for a single product, the system buckled under every new product launch or small pricing change. Months of rewriting code became the norm, fixing problems as they arose, instead of outsourcing the solution to a platform like Metronome, built for usage-based billing. Along the way, we faced sales tax errors, revenue recognition headaches, overcharges (followed by refunds), revenue leakage, and other billing mishaps. It got so bad that we resorted to manually calculating our revenue waterfall—25,000 lines in Excel—which crashed computers and nearly broke the accounting team’s spirit. Building a proper billing and growth team was a two-year battle—and it even became a running joke at our exec offsites. It’s a notoriously complex initiative, involving almost the entire organization—GTM, P&E, Finance, and BI—with each department bringing competing interests and priorities to the table. This uphill effort underscored a hard truth: billing is a cornerstone of any business. It must work flawlessly. It must scale. It’s the foundation for launching new products, adopting flexible pricing models, and driving growth. Yet, billing often flies under the radar. Startups leave money—and insights—on the table by overlooking it. Without strong systems and reliable partners, businesses risk more than lost revenue; they miss opportunities to better understand their customers. 1️⃣ Investing in an in-house billing system, however well-intentioned, is a distraction. Outsourcing this function and focusing on what truly matters is the smarter path. 2️⃣ With AI transforming pricing from seat-based to usage-based—and even outcome-based models—companies will face entirely new challenges. Deciding what counts as an “outcome” alone will spark scorched-earth debates. 3️⃣ Nobody cares about billing until it is too late, but ignore it at your own risk. (Chatgpt really doesn't understand "old-timey accounting visor" this is the best that I could do, as the other photos were simply bizarre)

👀 They didn’t have a revenue problem. They had a visibility problem. A few months ago, I worked with a multispecialty clinic that should’ve been thriving. Their schedule was full. Their providers were busy. But their bank account? Telling a different story. Every month, $22K–$25K was missing — and no one could explain why. So, we took a closer look. Here’s what we uncovered: 📝 Claims left in draft for up to two weeks ⚠️ Eligibility checks rushed or skipped 🔧 Charges submitted without necessary chances 📬 Rejections from the clearinghouse — unnoticed. The truth? Their revenue wasn’t being lost at the back-end. It was slipping away before the claim ever left the door. 🧠 In my experience across multiple practices, this pattern is surprisingly common — yet rarely talked about. Front-end workflow issues quietly drain revenue long before denials ever hit your radar. Sometimes, the fix isn’t complicated. It’s just overdue. Share your thoughts! #Medicalbillingchallenges #revenuecyclemanagment #healthcare

Imagine it's the last week of the quarter and you can't log in to any of your systems. Sales can't see customer records, quote deals or even access their email or sales presentations. At OneLogin, we had an outage at the worst possible time. There's no ideal time for systems to go down, but the last few days of a quarter – it doesn't get worse than that. I remember one customer got particularly upset because their sales team couldn't get into Salesforce to close deals during the most critical 48 hours of their year. It was thankfully only a small outage that was resolved quickly, but we felt the ripples much further after. At OneLogin, it was painfully clear how upset people got when they couldn't get into their apps. Sometimes, my brother (and OneLogin co-founder) and I would joke that we'd really picked quite the high-stakes category to build in. And yet, we moved to something even more sensitive - people's money. 😂 When you mess with billing, sending incorrect invoices or overcharging customers, the fallout can be devastating. There's significant operational risk in being a billing vendor. You're not just handling data or workflows, you're handling the lifeblood of a business. B2B subscription billing is a surprisingly hard problem to solve. You're not just billing every customer $50 a month. Customers have multiple subscriptions, a mix of recurring and usage-based charges with flat, tiered or volume based price structures. And on top of that you have discounts, free periods, price overrides, price adjustments, scheduled price changes, currency conversation, sales tax, refunds etc. And then there is dates! With multiple entities and customers in different countries, amendments and proration of charges, dates become one of the really tricky problems in billing. But this also means that it's ten times harder to do manually, which is why it's such a worthwhile problem to solve.

"Don’t make your billing experience your customer’s problem." That was the line that stuck with me after talking to one of the best revenue leaders I know. Recently, he joined a growth stage company and did what great revenue leaders do: he got close to customers. What he found was billing pain — everywhere. - Reps avoiding expansion motions because they didn’t trust how customers would be charged - CS teams spending hours each week deciphering customer usage & customer billing state - Customers confused or frustrated by invoices & how that tied to usage - A monetization model with 70 SKUs for 50 customers! So he rebuilt it — cleaner pricing tiers, clearer communication, annual contracts to deliver predictability. ASP went up. Customers were happier. And his team got to focus on selling, not apologizing for billing experience. But the systems underneath? Still messy. Still fragile. Still batch-loaded reports from a duct-taped, homegrown system. This is why we built Schematic. To give GTM teams the ability to: - Price, package, and update SKUs confidently and without code changes. - Show real-time usage and billing to customers (not a spreadsheet 30 days later) If your leading revenue and your billing experience is causing customer heartburn, let’s talk. Billing & pricing are critical extensions of a customer's experience with not just your product, but your business, including your reps. Billing should be a GTM tool — not a liability.

At a certain stage, every founder feels the pain of billing. Chasing unpaid invoices, tracking usage, and making sure nothing slips through the cracks starts eating up more time than it should. I talk to founders, COOs, and Chiefs of Staff all the time who push off fixing it. They know invoices are slipping through the cracks, but they assume it’s a single-point problem or just a billing system issue they can deal with later. But eventually, it becomes priority #1, because those small cracks turn into real gaps. And by the time they take action, they’ve already lost real revenue. Billing, collections, and usage tracking aren’t separate problems. They’re all symptoms of one broken process. Here’s how revenue actually moves: 1. Contract gets signed (Point A) 2. Usage or variables get tracked (Point B) 3. Invoice gets sent (Point C) If anything in that flow breaks, revenue disappears: 1. Contracts signed but never invoiced. 2. Usage tracked incorrectly, leading to under billing. 3. Invoices sent but never followed up on. We’re sharing the exact playbook we use to help startups fix this process for good. Stay tuned - but if you want to fix this problem for your company now, let’s talk: https://lnkd.in/gswAgidc.