AI training, setup, and support
Make room for the work only you can do.
Working Fluency AI is my AI consulting practice. I help law firms, small businesses, and nonprofits put AI to work on the research, drafting, and reporting that fill their week, from deposition outlines to grant applications to the monthly numbers. I do it through training, hands-on setup, and ongoing support.
Let AI take the routine work off your plate. I’ll set it up with you and teach you to keep it there, so your time goes back to serving your clients, building your business, doing what you’re passionate about, and being present for the people who need you.
Who I work with
Support built for your field.
AI for legal practice.
Verified fact chronologies, cite-checked briefs, and deposition outlines built from your own case files, with attorney review built in.
AI for law firms Small businessesAutomate routine tasks.
Automate routine tasks, take back your inbox, and see your numbers on one page, using the tools your business already has.
AI for small businesses NonprofitsMore time for the mission.
Data management and analysis, automated workflows, email management, and faster document creation for individuals and teams.
AI for nonprofitsWhat I do
Three ways to work together.
Working Fluency AI is my practice in Portland, Oregon. I’m Matthew Westerbeck, and I travel anywhere in North America for on-site work. The page for your field shows what this work looks like for you.
Workshops and the Claude Bootcamp
For small businesses and nonprofits, I teach one- or two-day Claude workshops built on the documents and tasks your team handles every week, so your team leaves already using Claude on its own work. A one-day workshop covers initial setup, basic use of the tools, and connecting Claude to your existing services; a two-day workshop adds a second day to build workflows on your own files, save the jobs your team repeats as skills it can run by name, and practice checking Claude’s work before anything leaves the office. For lawyers and legal staff, Shemia Fagan and I teach the Claude Bootcamp, built on your own case files. After either one, I offer ongoing remote work to build on it.
More about workshops and the claude bootcampHands-on setup
Together, we set up Claude on the files, email, and calendars you already use and connect it to the services your team works in, such as Microsoft 365, Gmail, Google Drive, Google Calendar, Slack, Dropbox, Notion, Canva, HubSpot, and Asana. Then we build the workflows your work needs and test them on real tasks before you rely on them.
More about hands-on setupOngoing support
Regular sessions after setup, so questions get answered and your workflows keep pace as your work and the tools change.
More about ongoing supportTestimonials
In their words.
“Matthew and Shemia’s Claude Bootcamp was like being shot out of a cannon.”
“It’s not as scary as it seems.”
“In person was definitely better for the camaraderie, and just hearing other people’s practices.”
Getting started
A conversation, then a clear plan.
Let’s talk, and we’ll choose the format that is right for you. A class is never a prerequisite.
A free 30-minute Zoom call
Talk through your work, current AI use, and what you’d like to learn, change, and implement. You don’t need a project brief or a chosen tool.
A tailored proposal
After we talk, I design a scope and timeline around your needs instead of handing you an off-the-shelf AI rollout. We agree on the format and cost before paid work begins.
The commitment
Private work starts with a minimum four-hour engagement.
All four hours are time we spend working together, in one session or across several. The work you don’t see, such as designing your scope, planning the timeline, and preparing for each session, happens on my own time and is not part of those four hours.
Meet Matthew
Experience behind the work.
My background is in nonprofits and federal contracting, and the daily work of running programs, including a six-month federal humanitarian program with a $30 million operating budget and a team of more than 400 people. I know what it’s like to carry a caseload, meet a reporting deadline, and introduce a new way of working to a busy team.
That’s the perspective I bring to AI. Start with the real work, understand how the tools can help, and confidently put them to use to realize and maximize real productivity and efficiency gains.
Claude Certified Associate - FoundationsA good first step
Start with a conversation.
Bring a question, a bottleneck, or an idea for doing things differently. We’ll work out where AI can help and what kind of support makes sense.
The first call is free, on Zoom, and needs no preparation. For on-site work, I travel anywhere in North America.