Billables.ai solves the problem every lawyer knows but won't admit: you're leaving 15-30% of your billable time on the table because you forget to record it. The tool runs passively in the background of your Microsoft 365 environment — Outlook, Teams, Word, SharePoint — capturing work activity and converting it into draft time entries with AI-generated narratives and automatic client-matter matching.

This isn't another timer app you'll forget to start. Billables.ai works without any behavior change from attorneys. It watches what you're already doing — emails sent, documents edited, meetings attended — and builds time entries you review and approve. For small and mid-size firms bleeding revenue through underbilling, that 15-30% billable recovery hits the bottom line immediately.


What Billables.ai Does

Billables.ai integrates directly with Microsoft 365 to passively capture attorney work activity. It monitors email correspondence, calendar events, Teams calls, document editing in Word and Excel, and SharePoint activity. From that data, it generates draft time entries with three critical components: time duration, AI-written narratives, and client-matter codes.

The AI doesn't just log "worked on document for 45 minutes." It generates billing-quality descriptions like "Reviewed and revised asset purchase agreement; addressed indemnification provisions in Section 7." The client-matter matching uses historical billing patterns and email context to assign entries to the right matter automatically. Attorneys review, edit if needed, and approve — then entries sync to your billing system.

Pricing

Billables.ai uses a per-attorney subscription model. Exact pricing isn't publicly listed and varies by firm size, but expect a cost that pays for itself if each attorney recovers even a few additional billable hours per month.

The ROI calculation is straightforward: if an attorney billing at $400/hour recovers just 3 additional hours per month (conservative given the 15-30% recovery data), that's $1,200/month in new revenue per attorney. Multiply across your firm. The tool typically pays for itself within the first billing cycle, which is why adoption has been strong among cost-conscious small and mid-size firms.

Who It's For

Small and mid-size law firms running Microsoft 365 — that's the bullseye. These firms typically don't have the infrastructure or budget for enterprise time-capture solutions, and their attorneys are the worst offenders when it comes to reconstructing time entries at the end of the day (or week).

It's particularly valuable for litigation and transactional practices where attorneys move between multiple matters throughout the day. The more context-switching your attorneys do, the more time they lose to imprecise or forgotten billing. Firms where partners regularly write off associate time due to poor descriptions will also see immediate improvement from the AI narrative generation.

What It's Not Good At

Billables.ai is Microsoft 365 only. If your firm runs on Google Workspace, Apple ecosystem, or on-premise Exchange, this tool doesn't work for you. That's a hard limitation, not a roadmap item.

It also doesn't replace your billing system. Billables.ai generates draft time entries — you still need your existing billing platform (Clio, LEAP, CenterBase, etc.) for invoicing, trust accounting, and client management. And for work that happens outside the Microsoft 365 environment — courtroom appearances, in-person client meetings, phone calls on personal devices — you're still relying on manual entry or other capture methods.

The Verdict

Billables.ai nails a specific, painful problem: attorneys are bad at recording time, and it costs firms real money. The passive capture approach is the right design choice — any system that requires attorneys to change behavior will fail. This one doesn't.

The Microsoft 365 requirement limits the addressable market, but for firms already in that ecosystem (which is most small and mid-size firms), it's a near-zero-friction addition that starts generating ROI immediately. If your firm's realization rate is below 90%, Billables.ai is probably the highest-ROI tool you can deploy this quarter.

The Bottom Line: Billables.ai is the simplest way to stop leaving money on the table — if your firm runs Microsoft 365, the 15-30% billable recovery pays for itself in weeks.

AI-Assisted Research. This piece was researched and written with AI assistance, reviewed and edited by Manu Ayala. For deeper takes and the perspective behind the research, follow me on LinkedIn or email me directly.