Auto-generate time entries from calendar and document activity logs
Law firms stop leaking revenue by automatically turning daily computer activity into drafted, ready-to-review timesheets. This is a highly repeatable offering that solves a universal, expensive pain point for any legal client using hourly billing.
The problem today
$16,000
lost per attorney annually in uncaptured billable time
3 hours
wasted per week per attorney on manual time entry
Marcus Chen is a litigation partner at a seven-attorney firm in Atlanta, billing at $425/hour with a full caseload and no paralegal support for his time entries. He knows he's leaving money on the table every month — he just doesn't know exactly how much, and that uncertainty bothers him more than he admits.
01The Problem
Time spent reconstructing a workday from memory still leaves billable hours unaccounted for and permanently unrecoverable.
Hallway calls, between-meeting reviews, and substantive message threads never reach the invoice because no capture moment existed.
Vague end-of-day narratives are the first entries clients dispute and the first partners cut before invoices go out.
One uncaptured hour per attorney per day at a $400 rate compounds into a six-figure loss with no line item on any report.
Falling two days behind means reconstructing work history from guesses — and clients cut entries that read like guesses.
Partners pulled into pre-invoice cleanup burn billable hours each month while cash flow stalls and client relationships fray.
02The Solution
Solution Brief
Fictional portrayal · illustrative
- Marcus bills $425/hr with no paralegal support for time entries
- End-of-day reconstruction from calendar captures maybe 80% of actual work
- Lunch emails, research detours, hallway calls never reach the invoice
- Every uncaptured hour is $425 gone — permanently
- Vague narratives trigger client write-downs on legitimately earned revenue
- Five-attorney firm loses $100K/yr with no report showing it happening
- Exhaustion-shortened entries fail billing audits and pre-invoice review
- Agent logs every document opened, email sent, call joined against active Clio matters
- Draft entries built in real time — specific, contemporaneous, audit-ready
- Marcus approves in ten minutes instead of forty-five
- Revenue recovery at $425/hr rates far exceeds software cost
- Clio referral commissions plus Microsoft 365 CSP margins build sticky recurring revenue across a legal book
“I billed 2.1 hours on a Tuesday that I know took closer to four. I just couldn't reconstruct the afternoon by the time I sat down to enter time. That happens more than I want to say out loud.”
— Marcus Chen is a litigation partner at a seven-attorney firm in Atlanta, billing at $425/hour with a full caseload and no paralegal support for his time entries
03What the AI Actually Does
Passive Activity Monitor
Runs silently in the background across Microsoft 365, web browsers, and legal research tools — capturing every document interaction, email exchange, calendar event, and Teams session as it happens, without requiring the attorney to log anything manually.
Matter Mapping Engine
Automatically matches each captured activity to the correct client matter using context from the attorney's existing Clio data — so time entries land in the right place without the attorney having to sort or reassign them.
Narrative Generator
Writes a professional, specific billing description for each time entry based on what actually happened — producing the kind of contemporaneous detail that survives client review, rather than the vague end-of-day summaries attorneys write from memory.
Draft Review Queue
Surfaces completed draft entries inside Clio Manage for attorney review and one-click approval — turning a 45-minute daily chore into a 10-minute checkpoint before entries are finalized and billed.
04Technology Stack
Clio Manage Advanced
$119/user/month (annual billing) or $149/user/month (monthly billing). MSP earns 20% lifetime recurring commission through Clio Partner Program = ~$23.80/user/month ongoing revenue.
Core practice management and billing platform. Serves as the destination for all AI-generated time entries. Provides client/matter database, billing r…
Billables AI (Full-Featured Plan)
$59–$99/user/month depending on seat count and feature tier. Negotiate MSP volume pricing for 10+ seats; estimated 15% resale margin.
Primary AI passive time-capture agent. Syncs with Clio Manage clients and matters, monitors Microsoft 365 activity (calendar, email, documents), captu…
Memtime Connect
$21/user/month (Connect tier required for Clio integration). Volume discounts available for 10+ seats. Estimated 20% MSP margin on volume purchases.
Alternative AI time-capture agent with privacy-first architecture. All activity data stored locally on the attorney's machine (offline-first), not in …
Microsoft 365 Business Premium
$22/user/month via CSP. MSP earns 15–20% margin = ~$3.30–$4.40/user/month. Increasing to $24.75/user/month effective April 2025 (new pricing announced).
Primary productivity suite providing calendar events, email metadata, document activity signals, and Teams call logs that feed the time-capture agent.…
Tempello
$0.39 per matched email. No subscription, no minimums, no long-term contracts. Estimated 500–2,000 emails/attorney/month = $195–$780/attorney/month.
Optional add-on for email-specific time capture. Scans Gmail or Outlook email, matches messages to Clio matters, and generates time entries for email …
Azure Active Directory (Entra ID) P1
Included in M365 Business Premium license — no additional cost
Identity provider for SSO to Clio, conditional access policies for time-capture agents, and OAuth 2.0 consent management for Microsoft Graph API permi…
Microsoft Intune
Included in M365 Business Premium license — no additional cost
Mobile Device Management / endpoint management platform used to deploy and manage the desktop time-capture agent (Billables AI or Memtime) across all …
05Alternative Approaches
Smokeball Built-In Automatic Time Tracking
$49–$89/user/month (full practice management + time tracking)
Instead of using a separate time-capture agent (Billables AI/Memtime) connected to Clio, use Smokeball as the practice management platform, which includes built-in automatic time tracking as a core feature. Smokeball passively captures all attorney activity and automatically generates time entries without requiring a third-party agent or API integration.
Strengths
- Single vendor, no API integration complexity
- Lower total software cost ($49–$89/user/month for full practice management + time tracking vs. $119 Clio + $59–99 agent)
- Simpler maintenance
Tradeoffs
- Smokeball has a smaller ecosystem than Clio
- Fewer third-party integrations
- Less flexible API for custom automations
- Less market share in legal tech (smaller community and fewer MSP resources)
Best for: Firm is not already invested in Clio, firm prioritizes simplicity over customization, firm has <10 attorneys.
Memtime (Privacy-First) Instead of Billables AI
$21/user/month
Use Memtime as the time-capture agent instead of Billables AI. Memtime stores all activity data locally on the attorney's workstation rather than in the vendor's cloud. The attorney manually reviews captured activity timelines and creates time entries from them, which then sync to Clio.
Strengths
- Superior privacy posture (data never leaves the workstation)
- Lower cost ($21/user/month vs $59–99 for Billables AI)
- Supports Windows/macOS/Linux
- Excellent for firms handling highly sensitive matters (national security, trade secrets)
Tradeoffs
- Less automation — attorneys must manually create entries from the activity timeline rather than having entries auto-generated and pushed to Clio
- No AI narrative generation
- No automatic client/matter matching
- Higher attorney effort required, which may reduce adoption
Best for: Firm handles extremely sensitive matters where cloud processing of activity data is unacceptable, or when budget is constrained.
Tempello Email-Only as Entry Point
$0.39/matched email, no subscription, no minimums
Start with only email-based time capture using Tempello ($0.39/matched email, no subscription) connected to Clio and Gmail/Outlook. This captures only email correspondence billing, not calendar events or document work. Expand to full time capture later after demonstrating ROI.
Strengths
- Lowest possible risk and cost — no subscription, no desktop agent installation, no change to attorney workflow
- Pay only for matched emails
- Easy to trial with skeptical attorneys
Tradeoffs
- Captures only email-related billing (typically 20–30% of total billable time)
- Misses calendar events, document drafting, legal research, and phone calls
- Limited ROI compared to full solution
- Requires expansion to a full agent later for material impact
Best for: Firm is highly change-resistant, managing partner needs proof of concept before committing to full deployment, or firm is a solo practitioner with very limited budget.
Microsoft 365 Copilot + Power Automate Custom Build
$30/user/month (Copilot license) + 80–160 hours custom development
Instead of using a dedicated legal time-capture vendor, build a custom solution using Microsoft 365 Copilot (for AI narrative generation) and Power Automate (for workflow automation) that reads from Microsoft Graph API (calendar, email, document activity) and writes to Clio via its REST API. No third-party time-capture agent required.
Strengths
- No third-party agent vendor dependency
- Leverages existing M365 investment
- Fully customizable to firm's exact requirements
- Microsoft's security/compliance posture covers all data processing
Tradeoffs
- Significant custom development effort (80–160 hours of developer time)
- Requires Microsoft 365 Copilot license ($30/user/month additional)
- No pre-built legal matter-matching AI (must build custom)
- Ongoing maintenance burden on MSP
- No vendor support for legal-specific features
- Total cost likely higher when factoring development time
Best for: MSP has strong Power Platform development capability, firm has very specific requirements not met by off-the-shelf agents, or firm already has M365 Copilot licenses deployed.
BigHand SmartTime for Enterprise Firms
Not publicly listed; typically $100–200+/user/month
For firms with 50+ attorneys or those using enterprise billing platforms (Thomson Reuters Elite 3E, Aderant Expert), replace the entire Clio + Billables AI stack with BigHand SmartTime, an enterprise-grade AI time capture solution designed for large law firms.
Strengths
- Purpose-built for large firms
- Integrates with Elite 3E and Aderant (which Clio/Billables AI cannot)
- AI-powered narrative generation with legal-specific language models
- Time-gap analysis
- Advanced compliance and audit features
- Dedicated enterprise support
Tradeoffs
- Enterprise pricing (not publicly listed, typically $100–200+/user/month)
- Requires enterprise billing platform (not compatible with SMB tools)
- Longer implementation timeline (3–6 months)
- Overkill for firms under 25 attorneys
Best for: Firm has 50+ attorneys, uses Elite 3E or Aderant for billing, has dedicated IT staff, and requires enterprise-grade SLAs and compliance features.
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