The Working Table Chicago: AI ROI Without Vanity Metrics

The Working Table Chicago: AI ROI Without Vanity Metrics

Don’t listen to a leader talk. Sit at the table and work the problem yourself.”

The Working Table Chicago is built around one simple idea:
Professional events should give you something more useful than a page of networking notes.

Each monthly edition begins with one real-world operating problem.

Attendees are grouped by the kind of work they actually do.
Then the tables rotate.

By the end of the evening, every group has worked toward a concrete framework that can be adapted after the event.

For the first Chicago edition:

AI ROI WITHOUT VANITY METRICS

The working question:

Where should a small or mid-sized team actually automate with AI - and how will we know the change created value?

The session does not begin with a software product.

It begins with the work.

THE WORKING FUNCTIONS

Opening tables are organized around areas such as:

AGENCY / CLIENT SERVICES

For people working across account management, client delivery, campaign operations, strategy, and agency workflows.

AGENCY / PERFORMANCE & CREATIVE

For people working across campaign execution, content systems, performance marketing, creative production, and related functions.

IN-HOUSE MARKETING

For people responsible for internal marketing operations, growth, content, lifecycle, brand, or campaign execution.

OPERATIONS

For people working on repeatable internal processes, reporting, coordination, systems, and operational improvement.

PRODUCT

For product managers, product operations, product marketers, designers, and adjacent product functions.

CROSS-FUNCTIONAL / GROWTH

For roles that regularly work across product, marketing, operations, and commercial teams.

Choose the lane closest to your current work during registration.

Final placement depends on the actual attendee mix.

THE WORKING PROBLEM

A team is considering using AI to automate several recurring workflows.

Possible candidates include:

• Weekly reporting
• Campaign summaries
• Content repurposing
• Customer-response drafts
• Internal research summaries
• Project-status updates
• Routine data transformation
• Repeated administrative workflows

But “AI can do this” is not enough.

The working question is:

Which task is actually worth automating - and what evidence would tell us the change worked?

ROUND 1 - DEFINE THE REAL COST

Begin with people closest to your own function.

Discuss:

What repetitive work is expensive because of time, delay, rework, mistakes, or attention?

The goal is to identify a meaningful work problem before discussing automation.

ROUND 2 - CHALLENGE THE AUTOMATION

Rotate to another function.

Ask:

What would have to be true before automating this actually makes sense?

Tables may consider:

• Task volume
• Consistency
• Exception rate
• Review time
• Data quality
• Human judgment
• Operational risk
• Adoption effort
• Maintenance

Not every repetitive task should be automated.

ROUND 3 - BUILD THE FRAMEWORK

The final working round creates an:

AI WORKFLOW ROI CANVAS

Each group works through six fields:

CURRENT TASK

What happens manually today?

CURRENT COST

Where does the work consume time, attention, rework, or delay?

AUTOMATION CANDIDATE

Which step is repetitive enough to test?

HUMAN CHECKPOINT

Where must a person remain responsible for review or judgment?

SUCCESS SIGNAL

What measurable change would indicate improvement?

STOP CONDITION

What result would tell the team to stop, redesign, or avoid the automation?

YOUR TAKEAWAY

The purpose of the night is not to produce a universal AI strategy.

It is to leave with a practical framework for evaluating one automation decision more carefully.

The AI Workflow ROI Canvas is a workshop framework.
It is not a financial projection, software recommendation, or guarantee of cost savings.