From Reactive to Predictive: Redefining What Good Looks Like in CS
Hosted in partnership with Dynatrace
About The Event
Join us on Thursday, 25 June 2026 for an evening of honest, high-level conversation at the intersection of AI, leadership, and the future of Customer Success.
This collaboration between Women of Customer Success (WoCS) and Dynatrace tackles one of the most pressing questions facing CS professionals right now: when AI can surface a churn risk months before a customer raises their hand, what does that mean for how we lead, coach, and measure our teams?
The bar for CS has shifted. The signals are earlier, the data is richer, and the tools are smarter. But the playbooks haven't caught up. This panel brings together CS leaders to get honest about what the shift from reactive to predictive really looks like in practice — not the pitch deck version, but the real one.
What We'll Cover
This isn't a product demo or a theory session. Our panel will dig into:
What "operationalising predictive signals" actually means — day-to-day, not in concept
How to retrain a team that was built for reactive CS — the coaching shifts, the resistance, the real talk
How "good" gets measured differently now — which KPIs are being retired, what's replacing them, and how you hold teams accountable to proactive outcomes
Where human judgment still wins — and why that's more important, not less, as AI takes over the data work
The honest tension: efficiency vs. depth — can predictive CS make relationships deeper, or does it just make churn prevention faster?
Speakers
Aishwarya Dwivedi is Director of Customer Strategy & Success at Adobe, where she helps organizations accelerate value realization, strengthen customer relationships, and drive business growth through customer-centric strategies.
Gabrielle Dracopoulos is a customer success leader at Rippling, focused on helping organizations scale customer outcomes through exceptional experiences, operational excellence, and customer-centric growth strategies.
Natalie Barrett is Vice President, Customer Success & Experience, APAC at Dynatrace, where she leads teams dedicated to driving customer value, fostering long-term partnerships, and delivering impactful business outcomes.
Who This Event Is For?
CS Leaders & Managers navigating how to redesign their teams and metrics around prediction rather than reaction
Individual Contributors — CSMs and Account Managers curious about how this shift changes their day-to-day and their career
Post-Sales Professionals across adoption, value realisation, retention, and growth who want to stay ahead of where the function is heading
Women transitioning into CS who want a clear-eyed view of where the role is going
What Will You Gain
Leave with practical perspective you can apply immediately:
A clearer picture of what predictive CS looks like when it's actually working
Frameworks for coaching a team through the reactive-to-predictive shift
Honest takes on which metrics matter now — and which are becoming noise
A stronger sense of where human judgment creates irreplaceable value in an AI-enabled team
Connection with CS leaders and peers who are working through the same questions
Agenda
6:00 PM – 6:25 PM: Arrival & Networking (Nibbles, wine & soft drinks)
6:25 PM – 6:35 PM: Welcome from WoCS + Dynatrace
6:35 PM – 7:10 PM: Panel Discussion
7:10 PM – 7:20 PM: Audience Q&A
7:20 PM – 7:25 PM: Close from WoCS
7:25 PM – 8:00 PM: Networking
Event Logistics
Drinks & Snacks? Yes — nibbles, wine, and soft drinks provided
Venue: Dynatrace Office, Level 18, 100 Miller Street, North Sydney, NSW 2060
Cost: $15
Spots are limited — register early to secure your place
About Women of Customer Success
We are the leading community for the best and brightest women in post-sales roles and leadership. Our mission is to connect, educate, and empower women to thrive in their careers and lead the way forward. With over 10 chapters worldwide — including Sydney — we are cultivating the next generation of women shaping the future of customer experience.
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