Choose the Session when
You need clarity quickly, have a single immediate question, and are not ready to commission a larger engagement.
Executive AI Productivity Session
Lowest-friction paid entryChoose your first useful AI move in one focused leadership session.
A 90-minute working session that maps the immediate problem, demonstrates relevant capability on a real task, and ends with a written decision memo. Decisive, not exploratory.
$500–$750 · Credited toward a qualifying engagement started within 30 days
MIT education · Former Amazon product leader · Longtime CTO · You work directly with Jason
When to choose this session
Best for a focused question or a first experiment.
Choose the Review when
You want a company-specific baseline, opportunity map, boundaries, and a 30-day plan across several roles.
Who should attend
The people who can decide and describe the work.
- The owner, CEO, or operating leader
- One or two people who know the recurring work in detail
- Anyone whose approval is needed to run a first experiment
What to bring
Real work makes the session useful.
- One recurring task or decision you want to improve
- Examples of the documents, messages, or reports involved
- The AI tools and business software your team already uses
- What would make a first step worth doing
What happens in the 90 minutes
A working session, not a presentation.
- 10–15 min
Business context and decision
Clarify the immediate problem and what a good outcome looks like.
- 215–35 min
Current work and tool use
Look at how the work is done today and what tools are already in place.
- 335–65 min
Relevant demonstration
Demonstrate ChatGPT, Claude, voice, or browser automation on a real task.
- 465–80 min
Competitive exposure, risk, and options
Identify where a faster competitor could create pressure, and the trade-offs.
- 580–90 min
Choose the next experiment
Decide the single most useful first move.
What you receive afterward
A concise written decision memo.
Current problem
A clear statement of the recurring work or decision addressed.
Recommended first experiment
The single most useful next move, with the tool or method.
Human review point
Where a person must check or approve before action.
Success measure
How you will know the experiment worked.
Immediate next actions
The concrete steps to start this week.
Whether a broader Review is warranted
An honest read on whether a Readiness Review is the right next step.
Session examples
The kinds of questions a session resolves.
“Where do we even start?”
Choose one recurring task and leave with a tested first method.
“ChatGPT or Claude?”
Compare tools on your actual work instead of in the abstract.
“Is this worth a bigger investment?”
Decide whether a Program, Workflow Upgrade, or Review is justified.
How the credit works
The fee applies to your next step.
The credit
The $500–$750 fee is credited toward a Readiness Review or 30-Day Program started within 30 days.
Booking and rescheduling
Scheduling is simple and explicit. Rescheduling with reasonable notice is fine; terms are stated at booking.
Boundaries
What the session is and is not.
- It is a focused decision session, not a full assessment
- It does not deliver a company-wide baseline or opportunity map
- It does not include implementation beyond a live demonstration
- Demonstrations use appropriate current tools; sensitive data should be sanitized
- It does not guarantee a specific return on investment
The goal is one clear, well-supported first move—decided in 90 minutes.
Why The Tomorrow Machine
You spend the 90 minutes with a senior operator.
The session is led by Jason Merkoski—not a sales team. Jason combines an MIT education, early Amazon product leadership, and current hands-on work across ChatGPT, Claude, voice AI, and supervised browser automation.
That means the demonstration is real, the trade-offs are honest, and the recommendation is not forced toward one vendor or a premature build.
- A real demonstration on your work
- Honest trade-offs, not a pitch
- A written memo you can act on
FAQ
Questions buyers ask first.
No. It is a paid working session with a written deliverable. If a larger engagement makes sense, the fee is credited toward it.
For a focused question or a first experiment, yes. For a company-specific baseline, opportunity map, and 30-day plan across roles, the Review is the better fit.
Bring sanitized examples for the demonstration. Sensitive workflows are handled with explicit decisions about access and vendors in a later engagement.
The $500–$750 fee is credited toward a Readiness Review or 30-Day Program started within 30 days of the session.
After the session
Where a session usually leads.
AI Productivity & Readiness Review
The broader assessment when you want a company-specific baseline and plan.
See the Readiness Review30-Day AI Productivity Program
When you are ready to make selected roles measurably better.
See the 30-Day ProgramWorkflow Upgrade
When the session identifies one workflow worth improving now.
See the Workflow UpgradeBook an Executive AI Session
Ninety minutes to your first useful AI move.
Bring one recurring task or decision. You will leave with a tested first method and a written decision memo.
$500–$750, credited toward a qualifying engagement · You work directly with Jason
Prefer email? Reach Jason directly at hello@tomorrowmachine.ai.
Based in Santa Fe, New Mexico. U.S. Mountain and Pacific working hours.
Book an AI productivity call
Pick a time for a free 20–30 minute AI Fit Call. We will look at how your team works today, where existing AI tools could help, and the smallest sensible next step.
What happens on the call
- 1.You describe the recurring work, pain point, or competitive pressure on your mind.
- 2.We decide together where existing AI tools could help—or whether a simpler fix comes first.
- 3.If there is a fit, we identify the smallest sensible next step: an Executive Session, Readiness Review, or 30-Day Program.
- 4.No sales team, no pitch deck. You speak directly with Jason.
Useful to bring
- The recurring work or decision you want to improve
- The AI tools and software your team already uses
- What would make a first step worth doing