CEO's Quick-Start Guide: Launching an AI Customer Service Pilot in 30 Days

Richard Casemore - @skarard

April 15, 2025

The Opportunity

AI can handle 70% of routine customer inquiries at a fraction of human agent cost. Companies like Klarna report AI assistants doing the work of 700 human agents. The technology is ready—the question is execution.

Day 1-5: Assessment

Audit Your Current State

Pull these numbers:

Monthly ticket/call volume by category
Average handle time by issue type
Current cost per resolution
Customer satisfaction scores
First-contact resolution rates

Identify Low-Hanging Fruit

Best AI candidates are inquiries that are:

High volume (justifies automation investment)
Repetitive (AI handles patterns well)
Low complexity (clear right answers)
Low emotional intensity (AI struggles with upset customers)

Common winners: Order status, password resets, return policies, account questions, FAQs

Day 6-10: Vendor Selection

The Major Players

Enterprise-grade options:

Intercom Fin (strong for SaaS)
Zendesk AI (integrates with existing Zendesk)
Salesforce Einstein (CRM integration)
Ada (dedicated AI customer service)

Emerging alternatives:

Sierra (founded by Bret Taylor)
Forethought (enterprise-focused)
Cognigy (European compliance)

Key Evaluation Criteria

Ask vendors:

How quickly can we go live with a pilot?
What's required for integration with our systems?
How do you handle escalation to human agents?
What languages do you support?
Show us accuracy metrics from similar deployments

Run a Quick Proof of Concept

Most vendors offer trials. Test with:

50 historical tickets
Measure accuracy of suggested responses
Evaluate tone and brand alignment

Day 11-15: Design the Pilot

Scope Narrowly

For a 30-day pilot, limit to:

One channel (chat preferred over email/phone)
One customer segment (new customers often best)
3-5 specific inquiry types

Define Success Metrics

Before launching:

Target deflection rate (% handled without human)
Accuracy threshold (% correct responses)
Customer satisfaction target
Maximum response time

Plan the Handoff

AI will fail sometimes. Design clean escalation:

Automatic trigger conditions (confusion, frustration, complexity)
Context transfer to human agents
No dead ends for customers

Day 16-20: Technical Setup

Integration Requirements

Minimum viable integration:

Connect to your website/app chat
Access customer account data (order history, etc.)
Handoff capability to human queue

Knowledge Base Preparation

AI needs training content:

Export existing FAQ content
Document common issue resolutions
Include brand voice guidelines
Flag topics requiring human handling

Testing Protocol

Before going live:

Internal team tests all expected scenarios
Test edge cases and failure modes
Verify escalation works smoothly
Confirm reporting dashboards function

Day 21-28: Launch and Learn

Soft Launch

Start with 10-20% of eligible traffic:

Monitor in real-time initially
Have human agents ready to intervene
Collect customer feedback actively

Daily Standups

15-minute reviews covering:

Deflection rate trend
Accuracy issues identified
Customer feedback themes
Adjustments needed

Iterate Quickly

Common early fixes:

Adding missing knowledge content
Adjusting confidence thresholds
Improving escalation triggers
Refining tone and responses

Day 29-30: Evaluate and Decide

Calculate ROI

Compare pilot period to baseline:

Cost per resolution (should decrease 40-60%)
Resolution time (should decrease 50%+)
Customer satisfaction (should maintain or improve)
Agent time freed (what did they do instead?)

Document Learnings

Capture:

What worked better than expected?
What challenges emerged?
What would you do differently?
What's needed for full rollout?

Make the Scale Decision

Options:

Expand: Increase traffic percentage, add inquiry types
Iterate: More pilot time with specific improvements
Pause: Technology or process not ready

Scaling Beyond the Pilot

If successful:

Month 2: Expand to 50% of chat traffic, add email Month 3: Full chat deployment, add phone IVR Month 4: Proactive outreach, multi-language Month 5: Advanced personalization, predictive support

Executive Checklist

□ Customer service metrics baseline documented □ Pilot scope defined (channel, segment, inquiry types) □ Vendor selected and contract signed □ Success metrics established □ Knowledge base prepared □ Escalation process designed □ Internal testing completed □ Soft launch executed □ Daily monitoring in place □ ROI calculated and decision made

The Bottom Line

AI customer service isn't future technology—it's today's competitive necessity. A 30-day pilot gives you real data to make confident scaling decisions. Start this week.