Need Strategic Advice: Major B2B Automation Opportunity ‼️

🎯 The Situation: Just wrapped a discovery call with a family office's general counsel - this could be my biggest project yet. Here's what I'm dealing with:

📊 Client Overview:

Mid-size family office (36 staff)
Managing 200+ investment vehicles
Processing ~10 vendor contracts weekly
15K+ vendor relationships needing data cleanup
45+ insurance policies with scattered renewal dates
Heavy manual processes across 7 departments

⚠️ Current Pain Points:

Legal counsel burning 30-60 min per contract review
Assistant playing telephone between departments, vendors, and C-suite
Using basic AI (Gemini) but everything downstream is manual
Clear workflow bottlenecks causing delays and frustration

💡 My Proposed Solution: Start with Phase 1 focused on vendor contract automation, integrating their existing stack (HubSpot, PandaDoc, Asana). Goal is workflow optimization, not just throwing more AI at the problem.

🤔 Where I Need Your Brain:

Scope Strategy: Better to laser-focus Phase 1 on vendor contracts only, or present a broader multi-phase roadmap covering their other workflow issues?
ROI Math: They won't share counsel's hourly rate. I'm thinking $400-500/hr industry benchmark for family office legal work - does that track?
Pricing Structure: Given their scale and $200K+ annual AI spend, should I stick with my usual approach or pivot to project-based pricing?

🛠️ Tech Stack Context: They're not tech-phobic - already using Gemini, HubSpot, PandaDoc, Asana, Google Drive (migrating to SharePoint). The foundation's there, just needs intelligent connecting.

💭 Looking for honest takes on strategy, pricing reality checks, or blind spots I might be missing. This could be a major breakthrough client but I want to nail the approach.

What would you do?

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