Most can recommend. I build with you.
I’m Courtney Toiaivao, founder of Grey Letter Advisory. I spent eight years running the research operation inside a Biglaw firm, and now I build and run AI systems.
Why now
This is the rare moment when being smaller is an advantage. The technology is moving faster than any firm can fully absorb. The firms that win won’t be the ones that buy the most tools. They’ll be the ones that adapt fast, learn the tools that fit them, and let each step build on the last.
Small and mid-size firms can decide and move while a larger firm is still forming a committee. The window is open now. This is the moment I built Grey Letter for.
Why me
Firms usually get one of two people: a consultant who knows law firms but can’t build, or a technologist who can build but has never run a legal operation. Both can recommend. I can enact. I’ve done both jobs: I know how the work flows because I ran it, and I can build what fixes it because I build these systems myself, every day.
As Director of Research, I grew the team’s annual billing from $100K to over $2M by running it like a business. I led a team that built a first-of-its-kind contract lifecycle management system for law firm libraries, and oversaw a 30-plus-person team and a $24M budget. I run operations that scale, and I know how to make a team, a department, or a whole firm better.
What you’re left with
Here’s what makes this different. I don’t install a tool and walk away. Your team already understands your work better than any outsider ever will. What’s missing is the translation: turning that understanding into systems the tools can run, and into process that connects end to end. That’s the part I build, with your people, so they can run it and keep improving it long after I’m gone. Even a small engagement leaves your team more capable than it was.
Who I work best with
I do my best work with firms that want to keep getting better, not just keep up. The leaders who light me up are curious, driven, big thinkers with real vision, the kind who do the work instead of just talking about it. Often they’re the ones bringing new faces into legal leadership. If that’s you, please reach out today.
Recognition
- vLex Fastcase 50 Honoree, 2025
- Speaker, LegalTech Connect: Law Firm Research & Innovation, 2026
- Panelist, Innovation in Regulatory Compliance Research, AALL Annual Meeting, 2026
- AALL Spectrum Article of the Year, 2023
Education
- M.S., Library & Information Science, Simmons College
- B.A., American Studies, Brigham Young University