We set up AI so your team can just use it
Your team uses AI.Your business doesn't.
Most teams stop at AI experimentation: ChatGPT for emails, maybe Copilot for slides, a few custom GPTs nobody maintains. Stairway to AI trains your team and puts the first AI workflows to work. Every workflow has an owner inside your company. When you are ready, we stay on as your fractional AI lead and ship new solutions every month.
Remote by default. On-site across the EU when it matters. English and Estonian.
Oliver Loit, founder. Leads every engagement himself. 1,000+ professionals trained in 20+ organisations.Why most AI engagements fail, and how this one is different.
Training is the start, not the result
Our unit of value is a production AI workflow that runs after we leave. Documented, with a named internal owner, and basic reliability in place. Demos don't count. Prompt libraries don't count. Workshop slide decks don't count.
Ownership built in, not bolted on
Every AI workflow we ship has a named internal owner before handover. That is the difference between a capability and a demo. Without an owner, most engagements die within six months.
Accountability to adoption
The retainer has a simple rule: if a solution agreed for the month is late because of us, we deliver it the following month at no extra cost. The monthly fee covers an agreed number of shipped solutions, not hours.
Three ways to work with us
Start with a half-day team workshop, or go straight to the Onboarding Partner programme. Near the end of the programme, teams can continue into a retainer.
Team AI Workshop
Half day · 4 hours · On-site or online
A practical first step for the whole team.
- •Survey first, so the session is built around your team's real tasks
- •More than half the time is hands-on, on your own document types
- •A practical prompting method and a clear rule for what data may go into which tool
- •Runs on the assistant you already license: Copilot, ChatGPT, Claude or Gemini
Best for teams that want a practical start before deciding on a programme.
AI Onboarding Partner
Fixed-scope programme · 2 to 3 months
Your team stops experimenting and starts producing.
- •Hours back on recurring work (report prep, first-draft content, research, meeting prep, customer response, internal communication)
- •Faster team output without headcount growth
- •First production workflows live before the programme ends, with internal owners
- •A Playbook your team uses after we're gone, so adoption keeps growing instead of fading
Best for teams who have tried AI but nothing stuck, with at least one internal owner available for the programme's duration.
Fractional AI Operations Lead
Ongoing retainer · Two tiers · 3-month minimum
More output, same headcount.
- •Senior AI leadership without a six-figure FTE hire
- •Operational leverage that grows month by month: every month adds a new capability that runs without us
- •Fewer sunk pilots: we only build what has an owner and a path to use
- •Tier A ships one production AI solution per month plus advisory; Tier B ships two and maintains your living AI Playbook
- •A solution that is late because of us is delivered the following month at no extra cost
Best for teams that have finished onboarding and want operational leverage that grows month by month without hiring a full-time Chief AI Officer.
Retainer rule: if a solution agreed for the month is late because of us, we deliver it the following month at no extra cost.
Not sure which path fits? Send a short message and we'll work it out together.
Concrete examples of what "shipped" means
A sample of the kinds of AI solutions we build inside client operations. Each one has a named owner, documentation, and is in active daily use.
Customer-facing product recommendation tool
Guided Q&A to match customers to the right product based on their specific situation. Built in Lovable, embedded on the client site.
Team-wide custom ChatGPT Project
Role-specific prompt libraries, internal brand voice, and internal knowledge baked in. Used daily across the team.
Functional-team AI assistant
For finance, support, or sales. Access to domain-specific templates, typical questions, and escalation logic.
Automated daily digest workflow
Pulls from multiple inboxes and sources, summarises, and routes to the right person each morning. Built in Relay.app or Make.com.
Content repurposing workflow
Turns one asset (a blog post, a webinar, a long-form document) into multiple formats with brand voice preserved.
Within the retainer, each of these can be scoped, built and handed over to an owner in a single month.
Good fit check
You are probably a good fit if:
- +You operate in Europe, the Nordics, or the Baltics
- +Your team already uses AI, but adoption is scattered and inconsistent
- +You want AI as operational infrastructure, not for show
- +You have at least one internal person who can own workflows alongside the programme
You are probably not a good fit if:
- −You want AI training as a box-ticking exercise, with no plan to use it afterwards
- −You want to fully outsource AI with no internal ownership
- −You have no internal capacity for an internal owner role
- −You want bespoke enterprise AI platform development (a different kind of engagement)
If you're not sure, send a short message and we'll work out whether there's a fit.
Ask if it's a fitRecent work
Three recent engagements, described without client names.
Energy company, about 50 people
AI Onboarding Partner programme on Microsoft Copilot in five groups. In the group sessions participants built AI assistants for their own daily work.
Event production agency, about 10 people
AI Onboarding Partner programme on Claude, in English. Each working group builds its assistants on its own real files, such as participant lists and rooming lists.
E-commerce brand selling worldwide
Fractional AI lead on a retainer: a product finder that guides customers to the right product, built in Lovable, and a prompt assistant the whole team uses.
Named case studies with results follow once clients have reviewed them.
What clients say about our workshops
“The training matched our expectations precisely. The focus was on real-world techniques, not theory. Everyone left with something they could put into practice immediately.”
“The training was like a breath of fresh air in the AI landscape. Well structured, substantive, strongly focused on the practical side.”
“The training this time was particularly useful and gave us many ideas to experiment with. Such a great group and a great trainer, who adapted skilfully to our wishes.”
Frequently asked questions
What is a "shipped AI solution"?
A production-ready AI workflow with a named internal owner, documentation, and reliability basics in place. Not a demo. Not a prototype. Not a prompt library. If the workflow isn't in active use with an owner six months later, it wasn't shipped.
How is this different from a consultant or an agency?
We work with a small number of clients at a time, and Oliver Loit leads every engagement himself. We work as a fractional Chief AI Officer. Pricing is tied to agreed results, not hours. Direct access to senior operational expertise, no handoff layers.
Where is Stairway to AI based, and where do you work?
We are based in Tallinn, Estonia. Most clients so far are Estonian organisations, including Estonian units of international groups. We work across Europe, remote by default and on site when it matters, in English and Estonian.
Which AI tools do you train teams on?
Microsoft Copilot, ChatGPT, Claude and Gemini, with no preferred vendor. We work on the assistant your company already licenses.
How do we start?
With a 30-minute discovery call. If there is a fit, you get a written proposal within 48 hours, with a fixed price for the workshop or the programme. The smallest first step is the half-day Team AI Workshop.
Can the training run in Estonian?
Yes. Every engagement can run in Estonian or in English.
Insights on AI adoption
Written from inside engagements. Published when there's something worth saying.
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30 minutes. No slides.
Start with a discovery call. We'll talk about your team's actual workflows and what you've tried with AI so far. You'll leave with either a clear programme proposal, a suggested starting point, or a straight answer that this isn't the right fit. No pressure, no obligations.
Or email info@stairwayto.ai directly. Response within one business day.