Why Law Firms Struggle to Convert Revenue into Cash

At ILTACON 2026, Zebraworks brought together leaders across finance, revenue, and technology to talk candidly about where cash gets trapped along that journey. The conversation quickly moved beyond traditional A/R:

• Bills sit waiting for attorney review

• Billing teams lose visibility once invoices leave their hands

• WIP accumulates while firms wait for the next billing cycle

• Invoices get buried in client inboxes

• Payment processes create unnecessary friction

• Staff spending valuable time manually following up on work that could be automated

The recurring theme was that revenue leakage rarely comes from one dramatic failure. It happens in the exceptions. A delayed prebill here, an invoice waiting to be sent there. Missing intake information. A manual collection reminder. A client who wants to pay but can't easily figure out how. Individually, these can look like small operational issues, but across thousands of matters and invoices, they become working capital trapped inside the firm.

Solving them requires more than another report: it requires visibility into where work is slowing down, better processes for moving it forward, and automation that removes manual intervention without taking control away from the people who need it.

Key Takeaways

1. The first bottleneck: getting the bill out the door

Before a firm can collect an invoice, it has to send it.

It sounds obvious, but the panel repeatedly returned to bill delivery as one of the earliest—and most consequential—places where cash gets trapped. Prebills wait for review. Attorneys hold invoices because they want to personally send them to clients. Billing teams wait for approvals, and once an invoice leaves accounting's hands, visibility into whether it was actually delivered can disappear.

As Luther Allin described, that creates a fundamental problem: the A/R clock can't really start until the bill goes out the door. An invoice sitting in an attorney's inbox for three days isn't simply a workflow delay. It's three additional days before the client can even begin processing payment.

At Williams Mullen, Director of Revenue Christine Purgason described a much more structured approach. With strong support from firm leadership, accounting controls bill delivery and copies the responsible attorney. The firm is approximately 85% billed by the 18th of the month: a level of consistency she attributed in part to clear policies and executive support.

Technology can then remove friction from the process. After implementing Zebraworks, Purgason said greater visibility into billing queues helped her team balance workloads and reduced the time required to get bills out by approximately a day and a half to two days.

The lesson isn't simply to send invoices faster. It's about understanding every exception standing between a completed bill and its delivery, and systematically removing the ones that don't add value.

2. Make it easier to pay, and firms get paid faster

Getting the invoice out is only half the equation. The client still has to pay it.

One of the simplest observations from the panel may also be one of the most important: firms spend enormous amounts of time optimizing internal billing processes while sometimes overlooking what happens on the other side of the invoice.

Purgason shared an example of a client who contacted her firm's COO with a problem most firms never want to hear:

Love to pay your bill, but I can't figure out how to pay you.

That's not a collections problem. It's an experience problem.

Clients increasingly expect the same simplicity from professional services that they experience everywhere else: receive the invoice, follow a link, see what is owed, and make a payment. They shouldn't need instructions to locate a client code or invoice number, call a phone number for assistance, or navigate an unnecessarily complicated portal.

The panel also discussed expanding payment options, such as ACH and eCheck, particularly when these methods can reduce transaction costs and make it easier for clients to act immediately.

Every additional step between “I want to pay this” and “payment submitted” is another opportunity for cash to remain outstanding.

Revenue acceleration therefore isn't only about what happens inside the firm. It also means designing the last mile of the revenue cycle around the person actually making the payment.

3. Visibility changes the revenue operation

Another theme surfaced repeatedly throughout the conversation: you can't accelerate what you can't see.

Billing and collections teams often know the firm's end results—total WIP, aged A/R, realization, collections—but those numbers tell them what has already happened. They don't necessarily reveal the operational activity creating those outcomes.

Where are prebills waiting for review? Which billing queues are overloaded? Which attorneys consistently delay approval? Why is a large bucket of WIP still sitting unbilled? Is it legitimately deferred because of the nature of the matter, or is something simply stuck?

Purgason described visibility as one of the original drivers behind her firm's Zebraworks implementation. She wanted a repository where she could see what was on each biller's task list and what remained in the queue. That visibility also allowed billers to back one another up when workloads became uneven.

Later in the conversation, the panel discussed how to identify large WIP balances and understand why they remain unbilled. A transactional matter approaching a closing may appropriately be deferred. A prebill sitting untouched because someone hasn't reviewed it is an entirely different problem.

That's the difference between reporting and operational intelligence.

A report tells firm leaders how much WIP exists.

Operational intelligence helps them understand what is happening to it and what needs to happen next.

4. Collections shouldn't depend on someone remembering to follow up

The panel's discussion of collections exposed another common source of invisible work.

Invoices arrive in crowded inboxes. Clients get busy. A bill that was intended to be paid gets buried under hundreds of other messages. Meanwhile, inside the firm, someone generates a reminder statement, sends another email, updates a spreadsheet, or hands the account to a collector.

Repeat that across hundreds or thousands of invoices and collections becomes an enormous administrative workload.

As the panel discussed, sometimes the reason for an invoice remains unpaid isn't a dispute or unwillingness to pay. The client simply needs to be reminded that it exists.

That creates an obvious opportunity for automation.

Routine follow-up can happen consistently without requiring someone to manually initiate every touch. Copies of outstanding invoices can accompany reminders, so the client doesn't have to search for the original. A client portal can provide a single place to see outstanding balances and access invoices.

Human intervention can then be reserved for the accounts and exceptions that require it.

That's an important distinction. The goal isn't to automate the relationship. It's to automate the repetitive work surrounding the relationship.

Collectors, attorneys, and firm leaders should spend their time on conversations where judgment and relationships matter—not recreating the same reminder email every week.

5. Technology doesn't fix a broken process by itself

For all the discussion of automation and AI, the panel was equally candid about why technology projects fail.

The answers weren't particularly technical.

Resources. Time. Data. Testing. Buy-in. Competing priorities. Change fatigue.

Successful transformation requires firms to understand the process they're trying to improve before layering technology on top of it. It also requires those affected by the change to understand why it matters.

That became particularly clear during the discussion of attorneys’ behavior.

Some attorneys want to retain control over sending invoices because it feels like an important part of the client relationship. Others have spent decades working a certain way. Simply introducing a new system doesn't make those behaviors disappear.

The firms represented on the panel described several approaches: strong top-down policies, greater transparency, mandatory onboarding, ongoing education, positive reinforcement, and even highly visible compliance reporting. The methods varied, but the underlying principle was consistent:

Changing workflow means changing behavior.

And that requires firms to make the better process easier—not simply mandate another piece of technology.

One of the strongest examples came from Purgason's implementation experience. A 40-year employee who had initially been resistant to change ultimately became a champion for the new billing process, helping bring the rest of the team along with her.

That's what successful automation looks like: not technology replacing people, but technology removing enough friction that people actually want to work differently.

6. The next opportunity starts earlier in the revenue cycle

Perhaps the most forward-looking part of the conversation came when the panel started looking upstream.

Many revenue problems become visible at billing or collections—but they often originate much earlier.

Incomplete intake information affects billing later. Delayed time entry can affect realization. Outside counsel guidelines influence how work should be recorded and billed. WIP accumulates before the monthly prebill cycle even begins.

By the time those issues appear on an aging report, the firm is already reacting to them.

The opportunity discussed by the panel is to take the intelligence firms accumulate throughout the revenue cycle and feed it back to the point where decisions are being made.

If a timekeeper is entering time, that's an opportunity to identify an issue.

If an attorney is reviewing a prebill, that's an opportunity to show the financial impact of a write-down.

If a new matter is being opened, that's an opportunity to capture the billing requirements that will eventually determine whether an invoice is accepted or rejected.

The panel discussed AI-enriched data specifically in this context: applying intelligence earlier in intake, time entry and prebill review rather than waiting until downstream problems need to be corrected.

Instead of asking technology to make a broken process faster, firms can begin using their data to recognize exceptions earlier, determine what needs attention and help people take the right action before revenue gets stuck.

The blind spot is between the systems

Taken together, the conversation points to a larger conclusion.

Law firms don't necessarily have a revenue problem. They have thousands of small operational moments that determine how efficiently revenue moves.

A late time entry. An incomplete intake form. A prebill waiting for review. An invoice sitting in an attorney's inbox. A client who can't figure out how to pay. A collection reminder someone has to remember to send.

Individually, they're exceptions.

Collectively, they're the revenue cycle.

The opportunity for firms is to make those exceptions visible earlier, automate the ones that don't require human judgment, and give finance, revenue and technology leaders the intelligence to focus on the ones that do.

That's how firms begin moving from worked → billed → cash with fewer places for revenue to get stuck.

Where is revenue getting stuck in your firm?

The most expensive exceptions aren't always the ones you know about. They're the delays, handoffs and manual work happening quietly between your systems every day.

Zebraworks helps law firms find those blind spots—and turn them into opportunities to accelerate cash.