Background: The Scheduling Struggle
Every CSM knows this pain — manually sending emails to schedule a renewal call, EBR, or Joint Success Plan meeting. The back-and-forth to find a time that works is not just tedious, it’s a poor use of high-value CS time. While many teams have tools like YouCanBook.Me or Calendly, they still rely on manual effort to send links and track outcomes.
We knew we had to automate and scale this process.
Problem Statement:
CSMs are manually reaching out to customers to schedule strategic calls (Renewals, EBRs, Success Plans), resulting in wasted time, inconsistent follow-ups, and lack of visibility on what’s working.
Solution: A Fully Automated Booking Funnel with Gainsight JO + Booking Platform + Gong
We implemented a Journey Orchestrator-based campaign that:
- Automatically sends personalized calendar booking emails to customers
- Tracks every step of engagement (open → click → booking → execution)
- Ties bookings to business outcomes like renewal conversions
- Measures ROI and performance by CSM, region, and program
Let’s break it down. 👇
Build Steps
Step 1: Change Management
We kicked off with strong change enablement using ADKAR/ Nudge Theory, aligning CSMs and CS Leaders on the “why.” The goal: save time, increase consistency, and measure impact.
Step 2: Create Email Templates in Gainsight
Each email was crafted for a specific purpose (e.g., Renewal discussion), including:
- Clear value proposition
- Direct YouCanBook.Me or Calendly link for the CSM
- Friendly, human tone
We designed 2–4 emails per Journey, including reminders with strategic escalation (e.g., final reminder from CCO).
Step 3: Build Journey Orchestrators
For instance - We created JOs based on key triggers. For example, in the Renewal Use Case, emails were sent:
- 120 days before renewal – from the CSM
- 90 days before renewal – from the CSM
- 60 days before renewal – from the CS Team Lead
- 45 days before renewal – from the C-suite
Each touch increased urgency and accountability.
Step 4: Capture Bookings via Calendly or YouCanBook.Me Webhook
We integrated Calendly or YouCanBook.Me’s APIs to send booking data into Gainsight’s Object. For each booking, we captured:
- Booking Date
- Contact Email
- Meeting Title / Subject
- Link to the original email campaign
This allowed attribution back to the JO that drove the booking.
Step 5: Match Meetings to Execution via Gong
We connected Gong’s Timeline Integration to Gainsight. This gave us:
- Meeting completion confirmation (based on Gong call)
- Topic validation (based on call title/transcript)
- Real signal of meeting quality
Data Model: Making It All Work Together
To tie it all together, we created a Universal Data Model in Gainsight:
| Object | Description |
| Email Log V2 | Capture email sent date, open/click status, JO name, contact email |
| BookingYCBM (Custom Object) | Captures who booked, when, and what for |
| Activity Timeline / Attendee | Verifies if the booked meeting was actually held (via Gong) |
We then created rules to Attribute outcomes (e.g., renewals, value realized)
Outcomes & Reporting
With everything in Gainsight, we built dashboards to measure:
- Email open, click, and bounce rates
- Booking conversion rate per JO
- Meeting execution rate (via Gong)
- Verifiable business outcomes – like % of booked meetings that led to renewals + associated $ value
Key Takeaways
- Automate with Intent: Use JO to drive urgency and accountability.
- Integrate Thoughtfully: YCBM/ Calendly + Gong + Gainsight = full-funnel visibility.
- Build Attribution Logic: Get credit where it’s due — show value.
- Drive Adoption with Change Management: Get your CS team bought in early.
Let’s scale CS without scaling manual effort. 💪
Tried something similar in your org? Have questions or ideas? I’d love to hear from you—drop them in the comments!