Boston · May 18, 2026 · HubSpot Cambridge
AI in Customer Success:
What's Actually Working
A working session for CS and post-sales leaders. Not a panel. Not a product demo. Two hours with 50 operators building a practical AI roadmap they take home and use.
50 seats · Applications reviewed within 24 hours
Why this is different
Most CS leaders have sat through 20 AI presentations in the last year.
Most CS leaders have sat through 20 AI presentations in the last year.
None of them left with something they built.
Every attendee leaves with a completed CS AI Stack Scorecard — built during the session against their own team. It maps your current workflows to the six AI use cases that are actually moving retention numbers, tells you where you are today, and shows you where to start. Not a handout. You build it in the room.
01
Operator-led, not vendor-driven
Every data point comes from real post-sales engagements across $1.8B+ ARR. No product pitches, no sponsored content.
02
You leave with a deliverable
The CS AI Stack Scorecard is a working document you built in the room. Bring it to your team the following week.
03
50 seats. No exceptions.
The room is capped and applications are reviewed. The point is peer density — people who actually run CS teams.
Agenda
Two hours. Built around a working session, not a keynote.
| 5:00 | Arrival and networkingLight bites, drinks, introductions |
| 5:15 | Opening: The state of AI in CSWhere teams actually are versus where vendor decks say they should be. Grounded in data from 4,500+ categorized churn events. |
| 5:35 | The six AI use cases that move retentionHealth monitoring agents, QBR automation, expansion intelligence, knowledge agents, conversation intelligence. What works, what breaks, what to build first. |
| 5:55 | Facilitated breakout roundtables + CS AI Stack ScorecardComplete the scorecard live at your table. Score your team's current state, data availability, tooling, and priority across each use case. |
| 6:40 | Group close: what the room foundTwo or three tables share their top scorecard finding. Open discussion. |
| 6:55 | NetworkingKeep the scorecard. Continue the conversation. |
Speakers
Practitioners. Not keynote speakers.
CK
Collette King
Product Lead, Service Hub · HubSpot
Leads product for HubSpot's Service Hub. She'll cover where the platform is headed for post-sales teams and what's on the roadmap for CS leaders building inside HubSpot.
JN
Jay Nathan
CEO, Balboa Solutions · Co-Founder, Gain Grow Retain
Former CCO and COO at Higher Logic. Co-founded Gain Grow Retain, the world's largest Customer Success leadership community. 20+ years leading CS and go-to-market functions.
JK
Jeff Kushmerek
Founder, Infinite Renewals
25 years in CS and professional services, including VP PS through a 2012 IPO. Has categorized 4,500+ churn events across PE-backed SaaS. Author of Retention Starts in Implementation.
