Is My Team AI-Pilled?
The 5 levels of AI adoption and why a lot of AI advice is bad
Brought to you by…Deel
A lot can go wrong when expanding internationally. I’ve made many of those mistakes. So learn from Deel—what they’ve seen doing this thousands of times and in hundreds of different countries.
How should you hire? Contractor, through an EOR, or set up an entity
What are the risks? Compliance, financial, etc
What countries should you hire in? Each country has different rules and risks
Check out Deel’s International Hiring Guide
Becoming “AI-Pilled” is Existential
I have been spending lots of time figuring out what it means to become “AI pilled” and how I can help my teams/company become AI super users. It’s my #1 priority. It’s existential.
AI-Pilled: Realizing AI will change everything. You reimagine your role, current processes/workflows, and what is possible. Your family and non-work friends hate you because AI is all you talk about.
The AI threat is existential in two related ways:
Your role/career
Your company
They are related. Companies that are going to succeed in an AI world are the ones that push their teams on AI and set high expectations. Employees win because they become AI experts (which is good for their career). Companies win because their employees are AI experts, which drives innovation. We are in an “accelerate or die” moment.
Side Note: Just because your company is “AI-pilled” doesn’t mean your job is safe. AI may still disrupt your role or employee layoffs may be necessary, but your chances of success are greater either at your company or finding a new role if your company is “AI pilled”.
AI Lies on LinkedIn
You are not going to become AI-pilled by consuming LinkedIn garbage like “Steal These 5 AI Prompts” or “The Prompt Framework For an AI-First CFO.”
If you take nothing else from this post, remember this: The best way to become an AI expert is to just start building with AI.
Not all AI content is useless, but 90%+ of what I have seen isn’t helpful. I will occasionally post interesting stuff I am building with AI, but the objective is not for you to “steal my prompts”. It is so folks can see what is possible.
Just go build something. We are all builders now.
The Levels of AI Adoption
AI feels like magic. Even when you are doing some of the most basic stuff. For that reason, I talk to many CFOs who incorrectly believe their company/teams are AI experts because everything that they are doing feels like magic. The reality is that most of them are just scratching the surface.
There have been quite a few good articles on the stages of AI adoption (see posts by Ann Miura-Ko and Geoff Charles, which inspired some of my framework below).
Level 1 (Noob): The Prompt Guy
Everyone starts here. You have played with AI chat interfaces personally, but now you are trying to use it for work. AI can’t complete anything end to end because nothing is really connected. Everything is individual prompts.
Reconcile this account
Summarize this contract and look for rev rec issues
Review this board deck
It certainly feels magical and you save some time, but nothing has significantly changed.
Finding the noobs? Daily AI usage may be high, but token usage will be very low because they aren’t building real workflow/process changes.
Level 2 (Casual): The “Magic” Feeling
The finance team has some shared context and maybe a few AI tools wired into workflows. AI starts to become part of how the team operates.
Shared prompt library for variance commentary
Monthly close checklist with AI-drafted flux explanations
Board deck narrative auto-drafted from the actuals
Individuals are using AI (and it makes them meaningfully more efficient), but nothing has really changed at the company. Headcount is similar. Each user creates things independently so efficiencies are limited and are tightly tied to people (if someone leaves, it breaks).
Level 3 (Pro): Systems Are Talking to Each Other
Agents work across systems by themselves. Real work is starting to happen with zero or minimal human intervention. This is the stage where folks start talking about layoffs due to AI because roles or entire teams no longer feel needed.
Agents pull from CRM, billing, and rev rec schedules to flag revenue risks before quarter close
Spend agent auto-categorizes, flags policy violations, drafts the exception memo
Shared skills/agents that capture how finance does things
Non-finance people self-serve 80%+ of their finance questions
Level 4 (Cracked): Company Processes and Org Designs Change
Processes and teams have changed to adapt to AI’s capabilities. All core systems are connected to AI and agents are set up to perform work across systems automatically. Headcount shrinks (at least relative to scale) and org structure changes.
Procurement, AP, and vendor management collapsed into one person with an agent stack. It used to be a team of five
Forecasting model auto-updates each cycle and flags variances before FP&A sees them. Company goes from 3 analysts to 1.
Contract review agent has learned from the last 200 redlines and handles 80% of standard MSAs without legal review. Legal team doesn’t make any more hires as the company triples revenue.
Level 5 (Creative Mode): Infinite Possibilities
In many games, there is a “creative mode”. Unlimited resources, you can’t die, normal game rules don’t apply, etc.
AI is continually advancing. Each new model unlocks new possibilities that weren’t conceivable just a few weeks earlier. The learning and building won’t stop anytime soon. Companies need people who are excited by “creative mode”.
In a couple of months, there might be a better way to do things with AI that you just barely finished. Folks have to be willing to destroy the old process and recreate again (better).
There could be single-person accounting, FP&A, or other departments at larger scale companies for those that reach level 5.
Some Tips on Becoming AI-Pilled
Create the right culture. Companies need builders. Not process followers. That is a culture shift for many companies/departments (particularly at more scaled companies). Leaders need to be building too. Having leaders be one of the first to build something cool with AI lights a fire underneath everyone else.
Make AI part of the hiring criteria. “What have you actually built?” “How would you do [X] with AI?”
Fire folks who aren’t adaptable. People unwilling to learn and create need to go. Things are moving too fast to keep them.
Host department AI hackathons. This gets the juices flowing on what’s possible. We did this for my org and almost immediately the AI projects started pouring in. Folks felt the AI magic and its possibilities. Claude usage spiked immediately afterwards as everyone was experimenting.
Incentivize AI adoption. Company rewards, spotlights, leaderboards, etc. If you have the right people, this will get everyone excited about AI and they will progress a lot faster to higher levels.
Give EVERYONE AI tools. Have seen too many CFOs limit budgets here (small token budgets or limits on who gets licenses) because the costs weren’t in the 2026 plan. This is a bad idea. You can’t let spending spin out of control, obviously, but the level of productivity gains far outweighs the cost. Find the budget. Maybe that means cuts elsewhere, but everyone should have an AI tool.
Don’t centralize AI work. “Our IT/AI folks understand AI better than anyone, so it’s more efficient for them to build and maintain the AI projects.” You will move too slowly if you are doing this. The successful companies will make everyone AI power users with the help of a few AI specialists.
Create an AI Czar/team. Not to just build stuff for folks. But to train, make sure they have the tools, and help guide/suggest next steps as folks move through the AI adoption levels. Their job is to guide everyone through the AI adoption levels and help take projects to the next level as needed. (needs to be hosted, has security considerations, etc).
In Summary…
Go and build stuff with AI. Experiment and see what’s possible.
The continual learning and required adaptability scares a lot of people (and companies). But it’s going to be needed to succeed.
Join companies that are going to push you. And invest in companies that are AI-pilled. A lot of people/companies claim to be AI-pilled when they are just barely scratching the surface.
Footnotes:
Check out this International Hiring Guide from Deel if you are looking at expanding internationally. It’s an excellent resource.
Want to sponsor? Email onlycfo@onlycfo.io
*nothing contained in this post is investment advice