# TimeSentry

Aiolum story: https://aiolum.com/story/timesentry/ · added 2026-11-05 · updated 2026-11-06

**In short.** TimeSentry (AI time tracking and billing for hourly professionals, United States): Live with paid plans and a MyCase listing, October 2026. Evidence grade E: no revenue figure was checked. Team: Two co-founders (one is a woman, per the company in January 2025); headcount not published. Launched 18 September 2023; still running.

AI time tracking and billing for hourly professionals · United States · AI-native · team of 2 to 10 · still running · group: Legal and law firms

- Outcome: Live with paid plans and a MyCase listing, October 2026 (evidence grade of the headline number: E; no revenue figure)
- Launch: 18 September 2023; months from launch to the outcome: 37
- Team: Two co-founders (one is a woman, per the company in January 2025); headcount not published
- Outside funding: Less than US$1M in outside funding, as the company stated in January 2025
- Main factor: Integrations
- Meters, 1 to 4: evidence strength 1, copyable pattern 2, capital needed 2
- Tags: AI-native, Small team, Funded, Running, B2B, Legal tech

Links:

- Visit timesentry.ai: https://timesentry.ai/

**The product.** Software that writes a lawyer's or consultant's timesheet for them. It connects to email, calendars, chat, calls, documents and practice management systems such as Clio and MyCase, and AI models turn that activity into draft time entries with a short description of the work, a client matter and a duration. The user reviews the drafts, and approved entries become invoices and reports.

**Why it worked.** Professionals who bill by the hour lose billable time because they rebuild their day from memory. The company built a tool that reads the work they already do and drafts the entries, then connected it to the billing systems that law firms already use.

Evidence grades: A = disclosed by a public company, a filing or a payment processor, or verified by one; B = two or more independent reports agree, or a journalist confirmed it; C = a founder claim that no one else verified; D = reported, not verified: one founder claim or a third-party estimate with no second source; E = no revenue figure found, so the headline is a non-money fact and the other facts carry their own grades; calc = computed on this page from graded facts.

## Summary

TimeSentry is an automatic time capture tool, software that records billable work from signals a person already leaves behind, such as sent email, calendar events and calls, instead of a timer that the person starts and stops. AI models from Anthropic, OpenAI and Google read those signals and draft time entries coded to the client and, for law firms, to UTBMS codes, the standard task and activity codes that many corporate clients require on legal invoices.

Joseph Frantz, the CEO, writes that he started it in the early summer of 2023 while working as a consultant, and the company gave 18 September 2023 as its founding date, in Brooklyn, New York. In January 2025 the company said it had two co-founders, more than 20 design partner agreements and less than US$1 million in outside funding. By October 2026 it sold a Professional plan, had a public changelog with releases most months of 2026, and was listed as an integration in the MyCase help center.

No revenue figure was found. The only money figure about sales is the company's January 2025 statement that its sales pipeline had "over $6K in Monthly Recurring Revenue", which describes possible deals, not money received. The page is grade E.

## Pricing

TimeSentry membership prices in November 2026, from the company's pricing and FAQ pages (grade C)

| Plan | Per month, billed yearly (US$) | Per month, billed monthly (US$) | Limit |
|---|---|---|---|
| Amateur | 0 | 0 | automatic capture and personal timesheets, no AI narratives or billing |
| Professional | 66.58 | 95 | per seat; AI-drafted entries, billing and invoicing, 20+ integrations |
| Executive | by invitation |  | staffing, team management, firm-wide analytics |

Membership is by invitation. The FAQ gives the Professional plan as US$95 per seat monthly or US$799 per seat yearly, which is about US$66.58 a month and about 30% less than twelve monthly payments of US$95 (US$1,140); the page shows 'Yearly, save 30%'. In January 2025 the company gave its price as US$300 a year per user, so the list price has risen. Executive has no published price.

## How much revenue does TimeSentry make? The numbers, graded

A two-founder legal and professional-services tool with paid plans and 20+ design partners, but no published revenue figure

| Fact | Value | Grade | Note | Sources |
|---|---|---|---|---|
| Status, October 2026 | Live, with a changelog entry dated 17 October 2026 | C | The company's changelog lists releases from January to October 2026, including Clio and Gmail or Outlook syncing changes. | [2] |
| Founded | 18 September 2023, Brooklyn, New York | C | Company's Startup Alley entry on LawNext, January 2025 ('9/18/2023. Brooklyn, New York'). | [1] |
| Founders | Two co-founders; Joseph Frantz is CEO | C | The entry says one co-founder is female; no downloaded source names her, so this page does not. Frantz signs the About page as CEO and podcast pages call him the founder. | [1, 3, 6, 7] |
| Team size | not published | C | No source gives a headcount. Nothing found suggests more than 10 people. | [1, 3] |
| Outside funding | less than US$1 million | C | The company's January 2025 entry: 'Less than $1M in outside funding.' No round or investor was named. | [1] |
| Design partners, January 2025 | more than 20 | C | Company entry: '20+ Design Partner Agreements with companies across consulting, legal, and digital agency sectors.' | [1] |
| Sales pipeline, January 2025 | 'over $6K in Monthly Recurring Revenue' in the pipeline | D | The company stated it once. A pipeline is deals not yet closed, so this is not revenue and is not the headline. | [1] |
| Price, January 2025 | US$300 a year per user | C | The company's entry. | [1] |
| Price, November 2026 | US$95 per seat a month, or US$799 per seat a year | C | FAQ and pricing pages. A free Amateur plan has capture without AI narratives. | [4, 5] |
| AI models | Anthropic (Claude), OpenAI and Google (Gemini) | C | Privacy policy: Claude runs the assistant; OpenAI transcribes calls and drafts some entries; Gemini drafts entries, tasks and summaries. Microsoft Azure hosts the service. | [8] |
| Practice management connections | Clio, MyCase, Filevine and others; 20+ integrations | C | FAQ and changelog. The MyCase help center has a TimeSentry AI article dated 29 January 2026. | [2, 4, 9] |
| Time from founding to the October 2026 status | 37 months | calc | Calculated: September 2023 to October 2026. | [1, 2] |

How to read this table: grade C values are statements on the company's own pages or by the company in a contest entry; grade D is a single company statement that no one else checked. No value is grade A or B, and no booked revenue figure exists in the sources.

## When did TimeSentry launch, and how did it grow? Timeline

From a consultant's idea in mid-2023 to a time capture and billing product sold to law firms, in about three years. Each entry carries its grade.

- **Early summer 2023** (grade C [3]): Joseph Frantz, then a consultant with a background in statistics, decides to use AI on the task he disliked most: timesheets.
- **18 September 2023** (grade C [1]): The company is founded in Brooklyn, New York.
- **January 2025** (grade C [1]): The company enters the ABA TECHSHOW 2025 Startup Alley vote with 20+ design partners, a price of US$300 a year per user and less than US$1 million in outside funding.
- **February and April 2025** (grade C [6, 7]): Frantz appears on two podcasts, Reinventing Professionals (12 February) and The Feedback Loop (22 April), to describe the product.
- **29 January 2026** (grade C [9]): The MyCase help center publishes a TimeSentry AI integration article.
- **April to October 2026** (grade C [2]): A macOS desktop app (25 April), custom agents built on Anthropic's managed agents platform, and folder-to-matter mapping for Gmail and Outlook (17 October).

## Why did TimeSentry work?

### Capture from signals, not timers

The product reads email, calendar, chat, calls and, with the desktop app, which application is in use, then drafts entries for review. The FAQ contrasts this with tools that rely on screen recording.

### Fit into the billing system the firm already has

Entries sync to Clio, MyCase, QuickBooks and others, and new matters can receive UTBMS code sets by default, so the firm keeps its system of record.

### Several model providers

The privacy policy names three AI providers for different tasks, so no single model is the whole product.

## How it was built

These details come from the company's privacy policy, FAQ and changelog. They are grade C.

- Claude models from Anthropic run the in-app assistant; OpenAI transcribes recorded calls and drafts some entries; Google's Gemini drafts entries, tasks and summaries.
- Microsoft Azure hosts the service, Twilio handles calls and text messages, and Auth0 handles login. Integrations connect through OAuth, so a user can revoke access.
- A desktop app for Windows, and for macOS since 25 April 2026, groups application-level activity into entries in 6-minute increments; the changelog says it records no screen and takes no screenshots.
- Custom agents are built on Anthropic's managed agents platform, according to the 25 April 2026 changelog entry.

Sources: [2, 4, 8]

## Who tried this before TimeSentry, and why did they fail?

Three legal technology companies in our database of failed startups tried to automate part of a lawyer's work and failed. The values below are from that database and are not independently verified.

The failed startups come from our database of dead startups, retold here in our own words; Its entries are AI-assisted summaries of public sources, so they carry no evidence grade.

### Atrium (2017 to 2021; funding US$75M; cause: Product/Tech Failure)

- Promise: Automate legal work for startups with software and a law firm.
- Why it died: The automation could not handle real legal complexity, so costs stayed like a traditional firm's.
- Record: 

### ROSS Intelligence (2015 to 2018; funding US$13M; cause: Competition)

- Promise: AI legal research faster than the established databases.
- Why it died: Lawyers stayed with the established research providers, which had decades of data.
- Record: 

### jEugene (2015 to 2018; funding US$120K; cause: Competition)

- Promise: Automatic error checks for contracts.
- Why it died: Rivals with newer AI moved faster, and law firms adopted slowly.
- Record: 

## What changed

The three predecessors tried to replace legal judgment or legal research, and law firms did not trust or adopt them fast enough. TimeSentry automates an administrative task, the timesheet, and every entry still goes to a person for review before it is billed.

It also sells into the systems that firms already use, Clio and MyCase, instead of asking them to switch. Whether that is enough is not shown: no revenue figure is public.

## Can one person copy TimeSentry now?

**Verdict: The idea, yes. The market is crowded.**

A small team can build automatic time capture on top of commercial AI models and the public APIs of email, calendar and practice management tools. The hard part is trust and distribution in law firms, where funded competitors already sell the same promise.

1. Pick a profession that bills by the hour and hates its timesheets.
2. Connect to the tools it already uses through official OAuth integrations, and draft entries for review, never final ones.
3. Get listed in the integration directories of the practice management systems.
4. Publish a clear privacy policy that names each AI provider and states that no data trains models.

**What is still open.** Other hourly professions with strict billing codes, such as accountants, engineers and architects.

## What could go wrong for TimeSentry?

- **What is not verified.** No revenue figure was found. The only sales figure is the company's own January 2025 Startup Alley entry, which said its pipeline had 'over $6K in Monthly Recurring Revenue'; a pipeline is deals not yet closed, not money received. We looked for a payment-processor profile, a founder interview with revenue and a funding announcement, and found none. A reader could look for a later interview or a press release on a funding round. The second co-founder's name and the headcount are not published in the sources read.
- **Privacy of captured activity data.** The product reads email, calendars, calls and, through the desktop app, which applications are in use, and sends content to Anthropic, OpenAI and Google for processing. The privacy policy says the providers may not train on it and that Google and Microsoft data is not stored beyond the task. Managers can review and approve team members' entries, so a firm that buys it for staff is also recording staff activity; the company describes it as a tool for the professional's own timesheet, with 'no spyware, no screenshots'.
- **Competition.** The company itself named Laurel, Billables AI, Ajax, Aderant and Intapp as competitors in January 2025, and its site has comparison pages against Laurel, Ajax, PointOne, WiseTime and others. The MyCase help center lists Billables AI, Ajax and Time Miner next to TimeSentry. Clio appears in the sources read only as an integration partner; no downloaded source describes Clio's own time capture, so that comparison is not made here.
- **Dependence on model providers.** Drafting, transcription and the assistant all run on outside AI models, and custom agents run on Anthropic's managed agents platform. A price or policy change at one provider would affect the product's cost or features.

## Sources

1. LawNext, January 2025: Voting Is Now Open: Pick the 15 Finalists to Compete at Startup Alley at ABA TECHSHOW 2025 in April — https://www.lawnext.com/2025/01/voting-is-now-open-pick-the-15-finalists-to-compete-at-startup-alley-at-aba-techshow-2025-in-april.html (grade C). Read the section on TimeSentry.ai. The company's own answers on founding date, location, price, traction, funding and founders.
2. TimeSentry changelog, read 5 November 2026 — https://timesentry.ai/changelog (grade C). Read in full. Release notes from January to October 2026.
3. TimeSentry About page, signed by Joseph Frantz, CEO — https://timesentry.ai/about (grade C). Read in full. The founder's account of how the idea started.
4. TimeSentry FAQ, read 5 November 2026 — https://timesentry.ai/faq (grade C). Read in full. Source for how capture works, integrations, security and monthly and yearly prices.
5. TimeSentry membership (pricing) page, read 5 November 2026 — https://timesentry.ai/pricing (grade C). Read in full. Plans and features.
6. Reinventing Professionals podcast, 12 February 2025: How Law Firms Can Use AI to Capture More Time — https://reinventingprofessionals.podbean.com/e/how-law-firms-can-use-ai-to-capture-more-time (grade C). Read the episode page. Names Joseph Frantz as the founder of TimeSentry.
7. The Feedback Loop podcast, 22 April 2025: 2 startups on time, AI for timesheets and wearables-based scheduling — https://shows.acast.com/feedback/episodes/2-startups-on-time-ai-for-timesheets-wearables-based-schedul (grade C). Read the episode page. Describes the product and names Joseph Frantz of TimeSentry.
8. TimeSentry privacy policy, read 5 November 2026 — https://timesentry.ai/privacy (grade C). Read the sections on sharing, Google API data and the AI assistant. Source for the AI providers and hosting.
9. 8am MyCase Help Center, 29 January 2026: TimeSentry AI — https://supportcenter.mycase.com/en/articles/12313481-timesentry-ai (grade C). Read in full. The integration listing and the related competitor integrations.
10. Database of failed startups, local export — /method/#dead (grade C). Local export. AI-written summaries, not independently verified. Source for the failed predecessors.

Contact: aiolum@livyden.com. Run TimeSentry? Send corrections or a verified figure to aiolum@livyden.com (subject: Correction: TimeSentry).