Webinar

Delivering Legal at Scale by Building Foundations of the Next Generation Legal Department

Watch Woolworths’ Ben share how the legal team scaled with Checkbox, from scrappy beginnings to 60+ apps, streamlining intake, NDAs, triage, and property workflows.

00:35 Intros: Evan (Checkbox) with Ben (Woolworths)
01:03 What is WooliesX? Digital, loyalty, media
01:43 Cartology, Financial Services (Wpay), back-end “digital sinews”
02:22 Scale question: size of legal vs. business
03:02 160–180k employees; rapid growth; 70% < 2 years
03:39 Then vs now: where Woolies Legal started
04:10 5 yrs ago: Google, no DMS/MMS; weak CLM use
04:49 Docs in Drive/Word; Gmail chaos
05:35 Today: still Google; matter mgmt + deep links = catalog
06:08 Not “poster child”; scrappy journey; VoT tools score up
07:25 Hybrid approach: use what IT has + add legal tech
08:16 Flow: open matter → folder link → Checkbox → Drive
09:25 Goal: make people happy with the process
09:51 Beyond NDA automation
10:27 NDA as internal training, not client-facing
10:54 Problem: legal doing mundane data-incident triage
12:04 Map the questions; only ~4 outcomes in practice
12:36 Intake always missing info; target: halve time (achieved)
14:29 Smart form: capture the right info first time
14:59 Replacing hotline/double-entry with Checkbox form
15:32 Rule set & harm “calculator” aligned to risk appetite
16:42 Endorsement; reporting; board visibility; 160k reach
17:41 Wins: funding, time, trust; pick visible use cases
18:16 Efficiency is icing; choose strategic projects
19:14 ~60 apps; test & learn; PWC NewLaw assist early
20:49 Other teams want in; build but they must maintain
21:52 Focus: capability; decentralized innovation
22:23 Bottom-up growth; paralegal empowerment story
23:37 New ways to “express” work; low barrier to build
24:28 Demo intro
25:07 Use case: Direct-to-Boot landlord license at scale
26:16 Blocks: forms, logic, doc gen, email; used by property
27:14 Simple, high-NPS; iPhone analogy

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