AI in Customer Success: What’s Real, What’s Not, and What Comes Next
Thank you to our sponsors! - Rod Cherkas, CEO of HelloCCO as well as our space sponsor, Workbox - River North. We are so excited to partner with you!
AI is everywhere in the Customer Success conversation right now, but for most CS leaders, the reality is still messy, early, and hard to explain.
At this event Rod Cherkas, CEO of HelloCCO Consulting and author of The Chief Customer Officer Playbook, will share insights from his recent AI in Post-Sale benchmark research on how AI is actually being used inside post-sale organizations today, and what that means for CS leaders in the months ahead.
What we’ll cover:
Where CS teams are actually using AI today, and where they’re not
Why productivity gains show up early, but measurable business impact takes longer
How executive and board expectations around AI are evolving
What CS leaders should focus on next if they want to move beyond experimentation
Bringing this to life, a panel of leaders will share how AI is actually being implemented across post sale and customer facing functions, followed by open discussion and Q &A focused on what this means for CS leaders today.
If you are a CS leader trying to figure out what AI really means for your team and what to focus on next, this conversation is for you.
Agenda:
5:30 PM - Arrival and networking
6:00-6:15 PM - AI Insights from Rod Cherkas
6:15 - 7:15 PM - Panel, Q&A, and discussion
7:15 - 7:30 PM - Final networking and closing of event
Food and beverages will be provided.
Moderator
Swati Garg is the CEO of Melo Associates and Chair of CuSP. She is also a Top 25 Global Customer Success Leader and serial entrepreneur who launched her first venture in 2016 with the creation of Melo Associates, an award winning talent firm specializing in Revenue roles. With a deep rooted focus on Customer Success, she also co founded CuSP, a Chicago based Customer Success community that fosters connection, collaboration, and career growth through events, meetups, and shared learning.
Panelists
CEO of HelloCCO and author of the best selling books The Chief Customer Officer Playbook and REACH. Rod consults with innovative companies across diverse industries to develop, execute, and scale strategies for their customer facing functions. He is currently leading a research effort on AI in Post Sale Organizations designed to help leaders understand how AI is actually being adopted, where teams are getting stuck, and what it takes to move from experimentation to operationalized value.
Director of Customer Experience at Aclaimant and award winning customer success strategist. Named a 2025 Top 100 Customer Success Strategist and ChurnZero Advocacy Hero Winner, Virginia has spent over a decade building high performing teams and designing data driven CS programs that drive retention and revenue growth. She is passionate about leveraging AI and automation to optimize customer experiences and is a frequent contributor to industry publications. She is also a strong advocate for equity, diversity, and celebrating every win.
Chicago based SaaS leader and VP of Value Enablement at seoClarity. Chris has spent more than 14 years building in SaaS, scaling teams, programs, and operating models across customer facing functions. That includes nearly a decade building and leading Client Success and consultative support teams for enterprise customers. Today he helps marketing organizations run SEO and AEO with clear workflows, strong adoption, and reporting that achieves business outcomes in both traditional search results and AI answers. He is currently focused on evolving business operations through practical AI integration.
Principal, Customer Transformation at Skan.ai. Shira works with large enterprise customers to identify how AI and data can improve operational performance. Her background spans enterprise SaaS, customer strategy, and operations, with a focus on translating complex signals into clear priorities and measurable impact. She leverages AI to uncover meaningful signals and reduce busywork, freeing up time to focus on the work that matters most.
About our sponsor(s):
**Rod Cherkas **is the CEO of the strategy consulting firm HelloCCO and the author of the best-selling books The Chief Customer Officer Playbook and REACH: A Framework for Driving Revenue Growth from Your Existing Customers. He consults with innovative companies across diverse industries to develop, execute, and scale strategies for their customer-facing functions. Rod is currently leading a research effort on AI in Post-Sale Organizations, designed to help leaders understand how AI is actually being adopted, where teams are getting stuck, and what it takes to move from experimentation to operationalized value.
*About Workbox - River North
Workbox's mission is to foster meaningful connections within a dynamic community!
Whether you're a growing startup or an established company, Workbox offers flexible coworking solutions designed to support collaboration, growth, and real business impact.
Workbox is more than just an office—it’s a community designed to help your team thrive.
If you're looking for a space that helps your team stay focused and feel connected, Workbox is the place to be.
**
About CuSP:
Learn more about CuSP: A Customer Success Community and join our Meetup group: https://www.meetup.com/CuSP-A-Customer-Success-Community/
Volunteer With Us: https://forms.gle/QYuwRcp3vEaofATz7
Sponsorship Signups: https://cusp.typeform.com/to/hfo8vI
Speaker/Panelist Signups: https://cusp.typeform.com/to/x9oMId
QUESTIONS?
If you have any questions, please contact Swati, Kimberly, or Parul via the CuSP Meetup group or [email protected].
#ConnectWithCuSP
CuSP is Sponsored by Melo Associates, a Recruitment Firm focused on Revenue Roles with a big focus on post sales, customer growth, and customer success roles. Check them out here: meloassociates.com
To learn more about the Customer Success Function, check out The Customer Success Association at https://www.customersuccessassociation.com/