Wolf Graduate Program · Case Study

Tessa Grosso
Advisor Success Playbook

March 2026

The prompt

The challenge: Our data shows that advisors who don't make their first booking within 60 days have an 80% churn rate. Currently, we have limited proactive intervention — most support is reactive when advisors reach out with questions.

The task: Design a comprehensive system to identify at-risk advisors early and deliver targeted support that helps them achieve first-booking success.

30,000 advisors
on the platform today
45 days
avg. time to first booking (successful)
90+ days
avg. time to first booking (churned)
80% churn
for advisors with no booking in 60 days
Main barriers to first booking
Client acquisition 40%Booking system complexity 25%Pricing confidence 20%Supplier relationships 15%
My solution
01
Smart sorting
The quiz

Every advisor answers 4 questions on Day 1. Based on their answers — do they have a client? are they tech-comfortable? — they're automatically sorted into one of three support tracks. No generic onboarding.

See the quiz →
02
Personal plans
Track-specific training

Each track gets a week-by-week plan tailored to their barrier — client acquisition, platform mastery, or pricing confidence. Schedules adapt to their goal date and available hours.

See the plans →
03
Detection agent
Proactive intervention

An AI agent monitors behavioral signals across all 30,000 advisors in real time. When risk is detected, it surfaces track-matched resources and triggers personalised outreach — automatically.

See the agent →
How it works end to end
Advisor joins
Day 1
→
Day 1 quiz
4 questions
→
Track assigned
A / B / C
→
Personal plan
AI-generated
→
Calendar sync
optional
→
Agent monitors
continuous
→
Booking #1
< 60 days

Explore each component of the system