The CX Files #27 - Jen Weaver

Explore the rapid evolution of the customer support career path at all levels and the future of these roles in the context of AI adoption.--Jen Weaver has 10+ years of experience in SaaS Customer Support and Success. She was the second support hire at YNAB (You Need A Budget), helping scale the team to over 70 people. She is currently a Customer Success Manager at On-Ramp, a podcast host, and curator of CX podcasts.--Jen discusses the critical transition of focus from support (reactive, costly) to success (proactive, profitable) even for B2C. We get into the operational challenges of implementing AI, why your knowledge base is now your most valuable asset, and how to evolve your career in a changing landscape.What we cover:☞ The difference between "Job Skills" (answering tickets) vs. "Career Skills" (politics and strategy).☞ Why the line between Support and Success is blurring for B2B companies.☞ The "AI Babysitter": A new essential role for support teams.☞ How to manage the transition from human-first to AI-first without losing the artisanal touch.☞ Practical advice for evaluating new tools (and avoiding sales fluff).This episode is also available on Youtube: https://youtu.be/Q4qxWO7bgFwWe need your help: Like and subscribe for more videos like this. ---You can save dozens of hours per month on the painful part of delivering reliable AI self-service with Helpfeel. Your whole org and customer base could be doing more valuable activities with our platform that has expert optimization included. 550+ Helpfeel business customers see ~50% reduction in tickets over their existing vendor plus increased lifetime value that results in 2.5X annual ROI on average.Book a demo now or watch a 2-minute video: https://www.helpfeel.com/en/--#CX #AI #CustomerService #leadership #knowledgemanagement #2026