Practical CSM Academy

Greatest Hits in Digital CX 2025
2025-12-18 20:00 - 21:00 UTC
Join our upcoming webinar where we are pulling the greatest hits together in one fast session with Eric Mistry from Zapier and Caroline Van Dyke from Skilljar by Gainsight.
Expect banter, highlight reels, a few memes, and of course, plenty of time for your questions.
What this is:

A fast, fun, Weekend-Update-style recap of the year
Hosted by Eric Mistry (Zapier) and Caroline van Dyke (Skilljar & Gainsight)
A live conversation featuring real talk, light (or heavy) banter, and YOUR live questions
The highlights you actually need before 2026 planning begins

What you’ll get:

The top shifts in Education, Community, and Digital CS
Why these programs now function as one connected learning ecosystem
The sound bites and takeaways that shaped the year
The templates, frameworks, and tools you’ll want for January
Clear signals on driving adoption, retention, engagement, and support deflection
People to follow, ideas to revisit, and advice to take or leave

Save your spot, we’ll see you there, ugly holiday sweaters and all!

Support x Success: Building Collaborative Customer Workflows
2025-12-22 22:00 - 23:00
We’ll show you how customer support and success teams can build collaborative workflows, share account context, and act on the same signals to improve retention and customer outcomes. You’ll learn how support tickets surface critical signals for health scoring and renewals, and what to look for in a unified post-sales platform that brings your entire post-sales team under one roof.

How Customer Success Teams Can Build Revenue AI Agents (Live Build)
2026-01-06 18:00 - 19:00
This 𝗟𝗶𝘃𝗲, 𝗵𝗮𝗻𝗱𝘀-𝗼𝗻 𝘀𝗲𝘀𝘀𝗶𝗼𝗻 will show 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 and 𝗽𝗿𝗮𝗰𝘁𝗶𝘁𝗶𝗼𝗻𝗲𝗿𝘀 how to build a revenue-focused AI agent that turns everyday customer signals into clear retention and expansion actions. You’ll see real examples, a live agent build, and practical ways to apply this inside your current CS workflows.
No prior 𝗔𝗜 𝗼𝗿 𝘁𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗲𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲 required!
𝗔𝗴𝗲𝗻𝗱𝗮
1. Why 𝗔𝗜 𝗔𝗴𝗲𝗻𝘁𝘀 𝗠𝗮𝘁𝘁𝗲𝗿 for CS in 2026
2. What a “𝗥𝗲𝘃𝗲𝗻𝘂𝗲 𝗔𝗜 𝗔𝗴𝗲𝗻𝘁” Looks Like in CS
3. 𝗟𝗶𝘃𝗲 Agent Build
4. How CS Teams Can Use This 𝗜𝗺𝗺𝗲𝗱𝗶𝗮𝘁𝗲𝗹𝘆

Customer Success Is A Lie: Why We Should Keep Believing In It!
2026-01-07 17:00 - 18:00
RSVP today to join me on Wednesday, January 7, 2026 at 11 AM CT, as I kick off the New Year with something you did not expect me to say about Customer Success!
A provocative, myth-busting session on why many Customer Success organizations think they’re practicing CS—yet still fail to deliver meaningful, repeatable, revenue-driving outcomes.

Webinar How to Talk Expansion Without Feeling Salesy
2026-01-10 18:00 - 19:00
Most teams know expansion is critical to driving NRR. What’s less clear is how to approach those conversations in a way that feels right for your business and your customer.
In this session, we’ll unpack how to navigate that moment, read the signals, lead with value, and make growth feel like a natural next step in the partnership.
What You’ll Learn

What expansion-readiness really looks like, and what to look for before you act
How to open the door to growth without putting the relationship at risk
Language that builds trust and keeps the conversation grounded in value
How CS and Sales can work together to support authentic, well-timed growth

Customer Success as a Growth Engine: How Early-Stage Startups Can Build Scalable CS Foundations
2026-01-15 13:00 - 14:00
Customer Success is one of the most underestimated growth drivers in early-stage startups. Yet the right CS foundations can dramatically improve retention, strengthen product adoption, but also find product-market fit a lot faster. In this practical 1-hour workshop, founders will learn how to use CS as a strategic advantage from day one.
What you will learn:
1. What Customer Success Really Is
A clear explanation of CS as a proactive growth function — on top of customer support.
2. How CS Directly Impacts Retention, Expansion, and Adoption
Founders will see how early CS habits translate into lower churn, higher activation, and more revenue.
3. Support as the Foundation of Customer Love
Simple steps to improve support quality and systematically gather feedback that shapes the roadmap.
4. CS in Early-Stage Startups
How to use CS as an early warning & insight system: what to track, what conversations to have, and which signals predict churn.
5. What to Build at Each Stage of Growth
A lightweight roadmap of CS priorities — from founder-led actions to scalable processes.
By the end of the session, founders will know:
how CS accelerates growth even with limited resources,
which early habits prevent churn,
how to collect and use customer feedback effectively,
what to focus on at each stage of scaling.
They walk away with clear, actionable steps they can apply immediately — without needing a dedicated CS team.
This workshop will be led by Zuzanna Ostojska and Aleksandra Puchta-Górska.
We are Customer Success consultants with 10+ years of experience supporting startups in building CS programs that increase retention and drive predictable revenue.
We work through mentoring, training, and project-based consulting — always with a focus on practical, founder-friendly execution.

Set up for success: Proven readiness tactics to accelerate identity outcomes
2026-01-21 10:00 - 11:00
Discover readiness tactics—frameworks, training, and metrics—to accelerate identity outcomes from day one.

Agents Unplugged: Your Playbook to Deploying Post-Sales Agents
2026-01-21 16:30 - 20:00
Forget the future. AI Agents are here, and they’re already rewriting the playbook for Customer Success. The best teams aren’t experimenting; they’re executing, using agents to scale impact, surface expansion signals, and prove automation can drive growth and connection.
Join us at Agents Unplugged for a behind-the-scenes look at how real teams are building, testing, and scaling Agents that make their work faster, smarter, and more human.
Key Takeaways You Won’t Want to Miss:
How leading CS teams are already using AI Agents to augment—not replace—their teams
Real deployment stories: what worked, what didn’t, and what they’d do differently
How to identify and prioritize the best Agent use cases across your customer journey
Why “human-in-the-loop” automation is the secret to scaling CS without sacrificing relationships

CCO Online: Making AI Real in Customer Success
2026-01-22 17:00 - 18:00
AI has moved beyond experimentation — it’s now transforming how Customer Success organizations deliver measurable business outcomes. Yet many teams remain stuck in the pilot trap, struggling to move from proof of concept to performance at scale.
​Join Matt Eldridge and Greg Fiore, Partners at Bain & Company, in conversation with Omid Razavi, Founder of SuccessLab, for an interactive live session on how Customer Success leaders are building an AI-first function that increases coverage, improves customer experience, and improves net revenue retention.
​Matt and Greg help technology and software companies strengthen their customer success and commercial operations through practical, data-driven strategies. Their work helps CS leaders set bold AI ambitions, redesign end-to-end customer journeys, and embed the change through communication, capability building, and new ways of working, so that pilots turn into enterprise-wide performance.
​In this live session, you’ll learn how to:
​Move beyond AI pilots to deliver enterprise-wide impact
​Rebalance CSM time and coverage by leveraging AI to allow CSMs to focus on strategic, high-value engagement
​Zero-base and redesign your most critical Customer Success journeys with AI-first workflows
​Drive adoption across people, data, and culture
​What you’ll gain:
​A practical, four-step roadmap for scaling AI in Customer Success
​Frameworks to improve retention, expansion, and efficiency by shifting CSM capacity toward higher-value customer outcomes
​Insights from Bain research and real-world transformations across leading B2B SaaS players
​Live Q&A with Bain and fellow Customer Success leaders

How to Talk Expansion Without Feeling Salesy
2026-01-27 17:00 - 18:00
Most Revenue teams know expansion is critical to driving NRR, especially as net-new business becomes harder to come by. What’s less clear is how to approach these conversations in a way that feels right for your business and your customer.
In this session, Megan Cassidy, Gainsight’s Head of Strategic Sales, and Pascal Debets, RVP of Account Management, will unpack how to navigate that moment, read the signals, lead with value, and make growth feel like a natural next step in the partnership.
What You’ll Learn

What expansion-readiness really looks like, and what leaders and CSMs should look for before you act
How to open the door to growth without putting the relationship at risk
Language that builds trust and keeps the conversation grounded in value
How CS and Sales can work together to support authentic, well-timed growth

Customer Success: Successful Communication as a tool of a CSM
2026-01-28 15:30 - 17:30
▶️ When? Jan 28, Wed, 17.30 – 19.30
​▶️ Where? Kaisaniemenkatu 4, 00100 Helsinki, 3rd floor, Refined office
​▶️ Topic: Successful Communication as a tool of a CSM
​▶️ Speakers: Steve Morrell and Valeria Markova
​▶️ Format: 30 min presentation, 60 min discussions in small groups

Unlocking Value Across Internal Teams – Turning Community Into An Internal Growth Engine
2026-01-29 16:30 - 17:30
Your customers are learning, sharing, and solving problems in your community every day. But is anyone inside your company actually using that goldmine?
Sales, Support, Marketing, and CS all should be paying attention to what’s happening in your community. Most aren’t. Which means insights get missed, opportunities get wasted, and Community stays stuck as “nice-to-have” instead of mission-critical.
Join this insightful discussion where you’ll learn how to turn your community into a go-to resource for your internal teams rather than just a destination for customers.
We hope to see you there!
Hosted by:
Meredith Estremo, Manager Enterprise Accounts, Gainsight
Jenny Weigle-Bonds, Customer Success Manager, Gainsight
Ainsley Steen, Solutions Consultant, Gainsight

Revenue-Grade Customer Success: Curing Health Score Overload Syndrome
2026-01-29 18:00 - 19:00
Health scores were created to manage risk, but many CS teams now overlook them.
If most of your accounts appear “green,” yet renewals still surprise you, this session will explain the reasons and outline actionable steps.
In this episode of Revenue-Grade Customer Success, we’ll examine Health Score Overload Syndrome, which occurs when health scores are used to predict revenue and explain customer behavior simultaneously.
In this live session, you’ll learn:
* Why health scores often fail to predict revenue?
* How mixing up health scores and forecasting can lead to false confidence?
* A practical method to tell customer signals apart from revenue signals.
* What CS leaders can change next week to make forecasts more reliable?
Who should attend?
CS Managers, Directors, CS Ops leaders, and senior CSMs who are responsible for renewals and revenue visibility.
This session offers practical, operator-level insights without tools, hype, or generic best practices.
Join us live and bring your questions.

Customer Success is a Lie: NPS is Emotional Noise
2026-02-04 17:00 - 18:00
RSVP today to join me on Wednesday, February 4, 2026 at 11 AM CT, for something you did not expect me to say about Customer Success!
Today’s Topic: NPS – Emotional Noise: Not a Churn Predictor
A provocative, myth-busting session on why many Customer Success organizations think they’re practicing CS—yet still fail to deliver meaningful, repeatable, revenue-driving outcomes

AI in Customer Success: Practical Use Cases for VOC and Renewals
2026-02-04 20:00 - 21:00
Customer Success teams are expected to use more AI.
The problem is most teams aren’t told how.
This hands-on workshop is designed for CS leaders and operators who want to move beyond theory and start applying AI to real workflows that improve retention, sharpen product insight, and support better decision-making.
Led by two operators building this work in the field:
Amelia Wampler, Co-Founder of Formata and Limitr
Rich King Gawlas, Founder & CEO of Onwards and Upwards
🧠 We’ll start with a clear, non-technical foundation:
– What it actually means to “use AI” in Customer Success
– How to think about models, agents, and workflows in practical terms
Then we’ll move into applied use cases:
1/ Turning Voice of the Customer into product-ready insight
Amelia will walk through how to set up AI-driven VOC trend analysis and translate customer signals into structured, actionable feedback Product teams can actually use.
2/ Building an AI-powered renewal risk agent
Rich will show how to design an agent that monitors renewal risk signals and supports proactive, data-informed renewal management.
———-
You’ll leave with concrete examples, mental models, and workflows you can adapt inside your own CS organization.
🤖 Who this is for
Customer Success leaders, CS Ops, RevOps, and Product partners who want applied AI, not hype.

How AI Agents Are Redefining Customer Success
2026-02-06 18:00 - 18:30
Customer Success hasn’t changed in intent — but it has changed in execution.
As customer bases grow, leaders struggle with churn and missed expansion because early signals are hard to surface, harder to connect across systems, and even harder to act on at the right time. Most post-sale work still happens too late and too manually.
In this live webinar, we’ll explore how AI agents are redefining Customer Success by surfacing proactive signals and taking post-sale actions with the right context and timing.
This session is for leaders who want a clear, first-hand understanding of how AI can support retention, expansion, and scalable post-sale execution in practice.

AI as a Strategic Partner for Customer Success Managers
2026-02-12 14:00 - 20:00
AI as a Strategic Partner for CSMs is a highly interactive working session where you actively use AI to rethink how you prepare for meetings, plan accounts, communicate with customers, and prioritize your work.
You’ll collaborate with fellow CSMs, experiment with real scenarios, and leave with practical tools you can apply immediately to your book of business.
This workshop is designed to create a fundamental mindset shift for CS professionals looking to evolve beyond basic AI usage.
For full details on the topics covered, agenda and pricing, please visit the event website.

What the Data Says About Customer Success in EMEA—and How to Use It in 2026
2026-02-12 15:00 - 16:00
European companies aren’t waiting for global consensus. They’re investing more in Customer Success, digitising faster than North America, and focusing on education-first, scalable journeys that put the customer in control.
Gainsight’s 2025 CS reveals how EMEA CS teams are evolving in real time—from how they’re leaning into digital and education-led journeys, adopting AI with greater intention, and evolving their operating models to stay aligned with revenue and outcomes.
Join Liam Gilleran, Gainsight’s RVP of Solution Consulting & Customer Success for a regional deep dive into the data, trends, and tactical shifts shaping the future of Customer Success across Europe.
Whether you’re pressure-testing your strategy or setting priorities for the year ahead, this session offers a practical, data-backed look at how Customer Success teams across Europe are turning 2025 insights into intentional action.
What You’ll Learn

Why European CS teams are setting the pace for Digital CS
How org structure is shifting to put CS closer to revenue and outcomes
Why European CS teams use GRR and retention metrics far less than North America

Oracle Integration Customer Success Webcast with UCAL & OneGlobe
2026-02-18 17:00 - 18:00
A Real-world Transformation Journey with UCAL

Consolidated automation strategy by migrating from UiPath to Oracle Integration

In this one-hour webcast, Oracle, UCAL, and OneGlobe come together to explore how Oracle Integration with native Robotic Process Automation (RPA) can modernize labor-intensive, business-critical workflows—without introducing additional platforms or technical debt.
With OneGlobe’s implementation expertise, UCAL automated two high-impact processes: Goods Receipt Note (GRN) Consolidation and Sales Order Processing — resulting in improved accuracy, faster processing, enhanced visibility, and the ability to redeploy staff to higher-value work.
Attendees will gain insight into:

How UCAL identified the right processes for RPA within Oracle Fusion
How native OIC integration and RPA capabilities work together in practice
Tangible business outcomes, including reduced processing time and improved financial visibility
Proven implementation best practices for scaling automation successfully

The webcast concludes with an open discussion and practical next steps for organizations considering or expanding Oracle Integration RPA as part of their enterprise automation strategy.

They’re Customers, Not Sheep: Individualizing the Customer Lifecycle at Scale
2026-02-18 17:00 - 18:00
In this fireside chat, Totango CEO Keith Frankel and Appcues CEO Ryan Barry will dig into what’s really breaking customer journeys… and why value, not lifecycle stages, should drive the experience.
From value-first growth to engagement and personas to lifecycle alignment, they’ll focus on how teams can stop treating customers the same, without sacrificing scale. Join us for a candid, unscripted conversation with strong opinions and real examples.
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DeepTarget Customer Success Webinar - February 2026
2026-02-19 17:00 - 18:00
Each month, DeepTarget hosts a Customer Success Webinar filled with industry news, helpful tips, innovations, and case studies to make your job easier. We highlight our best performing customers by announcing our Award Winners for the Campaign of the Month and the SuperSTAR of the month.
Each Webinar is unique and designed with you in mind. Learn how to grow your deposits, loans, revenue and customer loyalty through your DeepTarget platform.
Register Today!

AI in Customer Success: What's working, what's not, and what leaders are seeing
2026-02-25 14:00 - 15:00
AI is rapidly making its way into Customer Success teams, but most leaders are still unsure how much value it’s actually delivering.
In this webinar, Rod Cherkas, author of The Chief Customer Officer Playbook and REACH, will share insights from Wave 1 of his AI in Post-Sale benchmark research, based on responses from ~190 CS and post-sale leaders across B2B SaaS. The data reveals a clear pattern. While AI adoption is real and growing, most teams are still experimenting, focused primarily on internal productivity, and are struggling to translate those efforts into outcomes they can confidently explain to executives.
This session will not outline a future-state vision. It’s a grounded look at what CS teams are actually doing with AI today, where they’re getting stuck, and what leaders should be paying attention to as expectations around retention, renewals, and efficiency continue to rise.
In this webinar, you’ll learn:

Where CS teams are really using AI today and where adoption is stalling
Why productivity gains are easier to achieve than defensible business impact
The most common mistakes CS leaders make when rolling out AI internally
What the data suggests about AI’s role in retention, renewals, and customer health (and what it doesn’t show yet)
Practical guidance for moving from experimentation to more consistent, scalable AI usage across your CS team

This session will also include a live Q&A, giving you the opportunity to pressure-test the findings against your organization’s experience.

Overcome the customer relationship meltdown
2026-02-25 17:00 - 18:00
Too often, legacy CRM systems trap teams in a cycle of manual data wrangling, disconnected tools, and frustrated customers. The result? Declining productivity, poor experiences, and missed revenue opportunities. Watch this series to learn how to transform your CRM

Rethinking the Sales Playbook: What today's teams actually need
2026-02-26 17:00 - 18:00
Sales plans aren’t failing because teams are lazy—they’re failing because the playbooks are outdated. In this candid conversation, Mark Ward, Managing Consultant at Revenue Arc, and Glenn Haertel, Global Head of Sales at memoryBlue, unpack what it really takes to build high-performing sales teams in today’s complex, fast-moving environment.

Why Customer Insights Never Turn Into Action
2026-02-26 17:00 - 18:00
The gap between insight and action is solvable…once you understand how scattered knowledge can wreak havoc on execution.
Drowning in customer feedback, performance metrics and operational data, but still struggling to turn any of it into real change?
Many teams have plenty of insight, but execution breaks down when the information people rely on is hard to find, inconsistent or outdated.
The numbers back it up:

Half of executives say knowledge gaps and training issues prevent consistent delivery
One-third of employees rely on 10+ tools just to document processes
Employees spend 15+ minutes searching for the information they need in the moment

That friction slows teams down, creates inconsistency and puts customer experience at risk — which is exactly what we’ll unpack on February 26 in a practical discussion with Procedureflow’s Jaclyn Lo on what stalls execution and how teams move from insight to action.
In this session, we’ll cover:

Why customer insights fail to drive change, even when the data is clear
How fragmented process knowledge creates execution gaps across teams
What consistent execution looks like when information is accessible in the moment of need
Where leaders should focus to identify gaps, improve adoption and drive performance

Join the conversation to understand what’s really getting in the way of execution, and how teams are closing the gap between insight and action.

Behind the Data: How Digital Customer Success Is Taking Center Stage in 2026
2026-02-26 18:00 - 19:00
In this live session, we’ll go behind freshly released data to unpack what’s really changing, and why digital customer success, education, and community are moving from supporting roles to center stage in 2026.
You’ll hear directly from leaders actively changing how teams are structured, how community-led education works, and how success is measured in practice.
Get ready for a fast-paced mix of fresh benchmark data, real anecdotes from the field, and a forward-looking view of what’s coming next. Key topics include:

New benchmark data on where companies are investing in digital customer success, education, community, and AI
Real-world examples of how these changes are showing up today, from team structure and operating models to how leaders are redefining success
Practical perspective on how AI is accelerating change, and where human judgment, trust, and community matter more than ever

Plus get access to your own copy of the data report, so you can take the insights back to your team and leadership!
Speakers:

Jill Glynn, Senior Manager, Scaled Engagement, LinkedIn
Samantha Murray, Strategic Advisor & GTM Strategy for CX & Learning Tech

We hope to see you there!

A.I. Applications for Customer Success
2026-03-01 06:00 - 2026-03-14 07:00
Learn how artificial intelligence can enhance customer service and experience. This workshop focuses on using A.I. tools, like chatbots, to provide 24/7 support, resolve simple issues, and deliver personalized interactions through intelligent automation. Gain a professional edge with this expert-led, self-paced online workshop and earn a micro-credential that showcases your skills and sets you apart in today’s A.I.-driven workplace.
This program is offered in partnership with MSOE Center for Professional Education.
INSTRUCTOR:
Patrik Neuwirth, MSOE Adjunct Trainer
WHO SHOULD ATTEND:
-Customer success professionals seeking to apply A.I. for improved engagement and efficiency.
-Job seekers and career changers targeting roles in support, CX, or digital service delivery.

Fix the broken customer experience
2026-03-03 17:00 - 18:00
In this unfiltered conversation, John Bishara from Seismic will share how adopting an AI-native CRM transformed their customer service operations, delivering faster resolutions at lower cost. You’ll also hear from our experts on why service teams get stuck in fragmented workflows and manual triage, and how AI agents are changing the experience by resolving issues before customers even ask.

The Post-Hype Reality of AI in CS
2026-03-03 17:00 - 18:00
AI is increasingly part of the customer success conversation, but for many teams and leaders, it’s still early, and the impact is hard to explain.
Join Gainsight alumnus Rod Cherkas, CEO of strategy consulting firm HelloCCO and author of The Chief Customer Officer Playbook, Josh Schacter, SVP of Strategy and Market Development at Gainsight, and Casandra Brice, VP CS Americas at Zendesk, for an engaging discussion grounded in insights from Rod Cherkas’s AI-in-Post-Sale benchmark research.
You’ll learn:

Where AI is actually being adopted inside CS teams—and how deep it really goes
Why productivity improvements show up fast, but real business impact lags behind
How expectations from boards and execs are shifting
What it takes to move from experimentation to outcomes you can defend

If you’re under pressure to “do something with AI” but still struggling to show the value, this session is for you.

How To Align Revenue Teams Around The Buyer Journey
2026-03-12 - 2026-03-13
Are your revenue teams fully aligned with your buyer’s journey? 💰
Disconnected systems, rigid processes, and slow response times aren’t just frustrating buyers – they’re leaving revenue on the table.
In this complimentary live session with LeanData, we share how RevOps leaders are aligning revenue, marketing, and sales operations teams around the buyer journey.
Gain practical insights for eliminating friction across teams and discover how a strong orchestration foundation can transform complex operations into measurable revenue impact.
