There’s something about Berlin that sets the tone for honest conversations. Maybe it’s the raw creative energy, or the fact that it’s a city where experimentation is part of everyday life. 

Under the buzzing energy of Berlin’s thriving tech scene, the latest Customer Success Snack brought together some of the region’s most forward-thinking CS leaders for a morning of sharp leadership insights, candid conversations, and real-world strategies. Against the backdrop of a city known for both creativity and precision, our Berlin session zeroed in on the evolving challenges and opportunities facing Customer Success today.

Moderated by a powerhouse lineup, Giorgia Pedenzini, Lena Zimmermann, Kristin Gissberg, Leslie Boadum, Maximilian Richter, Andrés Calles Weill, Giovanni Serritelli, and Sally Stoewe—the session unpacked practical, actionable themes across CS processes, value communication, automation, digital engagement, and more. 

Here are the topics we covered:

1. AI & Prompt Engineering
2. CS Enablement and Scaled CS in 2025
3. Upselling together with Sales & Marketing
4. Conflict Management and Feedback
5. Client Change management, Success Plans & tooling
6. Communities, Playbooks, Automation, and Customer Engagement
7. Value-based communication, Time to value & Stakeholder management
8. For leadership only: CS Processes and Metrics

AI & Prompt Engineering

The ultimate aim of using AI in Customer Success is simple but powerful. Free up time to invest in stronger human connections. In our session about AI & Prompt Engineering, spearheaded by Lenna Zimmerman, Sally Stoewe and Maximilian Richter, we discussed in-depth the importance of how to use AI correctly, and in a manner that doesn’t make it seem like a bot to replace humans.

By automating low-value, time-consuming tasks, Customer Success Managers (CSMs) can shift their energy toward building relationships, planning for customer success, delivering strategic insights, and cultivating community.

After all, we don’t want to cut corners, rather be more proactive. This isn’t about cutting boosting your bandwidth to be more human, and more strategic.

With the right AI tools in place, teams are reclaiming hours each week. But where should that time go? To simplify:

• Community Building – Developing user groups, forums, or feedback loops.
• Proactive Outreach – Engaging customers before problems arise.
• Success Planning – Creating scalable, tailored success plans.
• Research & Strategy – Better prep for QBRs and account planning.
• “Back Office” Clean-Up – Tidying workflows, documents, and internal systems.
  

Where AI Is Making an Impact

We simplified the areas where we believe AI makes an even more significant change: 

Area	How AI Helps
User-Friendly Solutions	Create simple, visual tools to guide customers
Sales Support	Drafting handover forms, prepping context
Data Structuring	Collect and format info for clarity and accessibility
Error-Prone Processes	Faster development with fewer mistakes
Educational Content	Translate releases into clear, always-updated customer comms
Back Office Operations	Automate process management and documentation
Scalable CS Models	Apply AI across Enterprise to Digital segments
Data Protection	Use secure internal tools like Team GPTs to manage customer data safely

5 Guiding Principles of Integrating AI without Losing the Human Edge

1. Design for People First

AI should never feel like a barrier. Tools must be intuitive, accessible, and aligned with real customer needs. Whether it’s a chatbot or an internal knowledge assistant, the goal is the same: make it easy for customers (and teams) to get what they need, quickly and confidently.

Don’t just build for functionality; build for usefulness.

2. Let Data Guide the Way

With the power of AI comes the ability to process vast amounts of data, but insight beats information every time.

Use data strategically to identify where automation adds value, to personalise customer outreach, to make smarter decisions faster. Simply put, let AI surface patterns, but you should be the one to provide the context and nuance.

3. Respect Privacy at Every Step

Customer trust is sacred, which means using AI responsibly and ensuring data is protected at all times. The best practice instead is to build internal, secure tools like Team GPTs for prompt sharing and reuse, Private AI portals tailored to your workflow and Clear governance policies on data usage. Truly, it’s not just about compliance but more about earning and maintaining customer trust.

4. Keep Ethics Front and Center

Just because something can be automated doesn’t mean it should be. Always Be intentional, and Ask, “Should we automate this?”. Ensure every AI-generated output is immediately verifiable by a human. Use AI as an assistant, not an authority. Transparency, accountability, and critical thinking should guide every decision.

5. Preserve the Human Connection

AI can do a lot, but what it can’t build is trust, nor can it empathise in the moment, or read between the lines. That’s your job. So, while AI should support and amplify your work, it should never interfere with the emotional intelligence that drives great customer relationships.

AI can help you move faster and smarter, but the heart of Customer Success is still and always will be human.

Start, Stop ,Continue

Start	Stop	Continue
Think before you prompt. Build reusable prompt templates instead of starting from scratch every time.	Dumping info without intent. Don’t input data into AI without considering how to reuse or repurpose it.	Reusing effective prompts. Keep using well-performing prompts for company research, summaries, and planning.
Centralize prompt knowledge. Create a shared library of proven prompts across your team.	Manual by default. Don’t manually create tasks, emails, or reports if AI can help automate it.	Double-checking AI outputs. AI drafts are fast—but always validate the content before using it externally.
Automate health scoring. Feed AI your product logic to generate health scores or early warning signals.	Reprompting basic details. Avoid repeating context every time—use tools that remember (like ChatGPT’s memory).	Using data for strategy. Input product usage data and link it to strategic goals in QBRs or EBRs.
Explore deep AI tools. Use advanced features (bots, API workflows, deep-research credits) beyond basic Q&A.	Over-censoring drafts. Don’t waste time perfecting an AI draft—refine and send, don’t overthink.	Iterating prompts. Keep learning how prompts behave and evolve them as your needs grow.
AI-first mindset. Test AI for new tasks before reverting to manual tools or escalating.	Relying on AI without understanding. Especially with translations or rewording—know what’s being said.	Setting exploration goals. Try a new AI use case regularly (e.g., one new tool or workflow per month).

It’s essential to turn our attention to how we can effectively empower CS teams to operate at scale. This brings us to the next topic: CS Enablement and Scaled CS—two critical pillars that ensure teams are equipped with the right tools, training, and strategies to deliver consistent, impactful experiences across a growing customer base.

CS Enablement and Scaled Customer Success in 2025

Looking ahead to 2025 and beyond, the evolution of CS is clear. Teams must scale efficiently, collaborate effectively, and focus relentlessly on value. In our session, led by Leslie Boadum, we learned and expounded on the fact that achieving this requires a strong foundation of enablement, centred on smart tooling, open knowledge sharing, and the confidence to navigate complexity with purpose.

Start, Stop, Continue

Start	Stop	Continue
Implement a single source of truth for CS data and insights.	Using multiple tools with overlapping or redundant functionalities.	Evaluating tools regularly to ensure they align with evolving CS needs.
Introducing hybrid-friendly formats like virtual workshops and story sessions.	Gatekeeping knowledge and only sharing in silos or reactive settings.	Encouraging informal and structured peer-to-peer learning opportunities.
Using available insights to tie work back to customer outcomes.	Waiting for the “perfect” report or metric to act.	Practising storytelling to communicate customer impact clearly and persuasively.
Creating repeatable onboarding, training, and playbook resources.	Relying on ad-hoc training or knowledge held by a few individuals.	Leveraging cross-functional insights to build reusable CS processes.
Empowering CSMs to make decisions using directional data and customer goals.	Expecting black-and-white answers in complex customer scenarios.	Supporting experimentation and iteration in CS strategies.

This naturally sets the stage for the next frontier, which is upselling in collaboration with Sales and Marketing. As value realisation becomes clearer and customer relationships deepen, aligning across go-to-market teams is key to unlocking growth opportunities and delivering a seamless, customer-first experience.

Upselling together with Sales & Marketing

Cross-functional alignment is essential for scalable growth. When Customer Success, Sales, and Marketing operate as a unified front, upsell opportunities become more organic, timely, and successful. This section, moderated by Lena Zimmerman, explores how CS can better support upselling, what to stop doing to reduce friction, and what best practices should continue.

Start, Stop, Continue

START	STOP	CONTINUE
Building business cases during planning to support upsell conversations.	Using data poorly or not leveraging customer insights.	Joint engagement with users to drive upsell momentum.
Hosting joint event formats with Sales and Marketing.	Letting Sales handle upsells entirely on their own.	Using playbooks and case studies to guide upsell conversations.
Creating onboarding and enablement content (videos, academy modules).	Not involving decision-makers early in the upsell process.	Maintaining feedback loops to improve cross-team processes.
Establishing regular syncs and retros to align on goals and priorities.	Operating with internal misalignment and unclear role ownership.	Categorising and tracking upsell opportunities strategically.

Differing goals, communication styles, and ownership boundaries can sometimes create friction. That’s why developing effective strategies for conflict management and feedback is essential.

Conflict Management and Feedback

Conflict is inevitable in any high-growth environment, especially in Customer Success, where you sit at the intersection of customer needs, internal priorities, and business goals. How we handle conflict, internally and with customers, can either build credibility or quietly erode trust.

At the same time, feedback (both giving and receiving) is one of our most powerful tools for continuous improvement. But it needs structure, accountability, and most importantly, action.

So how do we shift from reactive firefighting to proactive, constructive engagement?

Start, Stop, Continue

START	STOP	CONTINUE
Implementing an “Escalation Button” for instant visibility.	Reactively managing conflict only after it escalates.	Staying calm and professional under pressure.
Evaluating how CS incentives align with transparency and collaboration.	Overloading internal teams with pings, Slack messages, or unclear asks.	Collaborating across departments on shared accounts.
Following structured escalation and feedback processes.	Ignoring early signals from data (product, engagement, history).	Sharing feedback, success stories, and updates proactively.
Setting clear boundaries for when and how to escalate.	Letting unclear ownership stall conflict resolution.	Acting as a customer advocate and closing the loop.

Proactively managing conflict and feedback lays a strong foundation of trust, but sustaining that trust requires helping clients navigate change successfully. Whether it’s onboarding, product adoption, or stakeholder turnover, change is constant. In the next topic, let’s explore how we can better support our customers through transitions while staying aligned on value and outcomes.

Client Change management, Success Plans & tooling

Let’s face it. Change is uncomfortable. Whether you’re rolling out a new tool, shifting internal processes, or asking end users to do things differently, you’re bound to face resistance.

But here’s the reality: if customers don’t change, they don’t succeed. And if they don’t succeed, neither do we.

To support real transformation, we elaborated on Client Change Management through the help of Maximilian Richter. In the session we learned that customer Success needs to evolve from a support function into a strategic change partner,guiding clients through transitions, aligning on shared goals, and leveraging the right tooling to drive adoption and results.

Why Change Management is a CS Imperative?

We’ve all seen it: the fear that “if the tool works too well, I might be replaced,” or “this isn’t the tool I chose.” These blockers show up as ghosting, slow onboarding, or internal churn.

Common Change Management Challenges:

• Decision-makers ≠ end users
  
• Internal messaging is inconsistent or unclear
  
• Fear of job loss or role change
  
• Lack of top-down commitment
  

So, how do we help customers move through change instead of getting stuck in it?

 Practical Solutions for Change Enablement

1. Multithread early and often.
   Don’t rely on one champion. Find the enablers and influencers across teams who see the value and can spread it.
   
2. Bridge the gap between C-level and users.
   Involve decision-makers in driving adoption. Incentivise tool usage and highlight how it supports team goals, not just executive metrics.
   
3. Bake trust into your strategy.
   Avoid buzzwords. Offer practical advice and clear direction. Sometimes people simply don’t know what a term or strategy means, and are too afraid to ask.
   
4. Visualise change and reduce fear.
   Use kickoff decks with a “stakeholder slide” that defines current roles vs. future roles, showing how the tool supports each person, not replaces them.
   
5. Celebrate quick wins.
   Lower the barrier to entry and give users a fast path to success. Highlight power users (with care), and create positive momentum by showcasing results transparently.
   
6. Make it human, and still  fun.
   Bake in regular check-ins, co-set deadlines, and don’t underestimate the power of small moments of joy throughout the process.

Start, Stop, Continue

START	STOP	CONTINUE
Involving C-levels in communications to encourage adoption.	Assuming the buyer will drive usage.	Acting as a customer advocate and guiding them through change.
Using stakeholder slides to outline “current state → future state” for end users.	Using buzzwords or vague strategies that confuse end users.	Multithreading across accounts—identify champions, influencers, and blockers.
Launching success plans from the very first client interaction.	Treating success plans as post-implementation or optional.	Regularly checking in and adjusting success milestones based on business priorities.
Leveraging tools like Everafter, Gong, and Loom to enable transparency and communication.	Relying on ad hoc tools or multiple disconnected systems.	Sharing best practices and customer wins across your portfolio.
Creating opportunities for “quick wins” to boost momentum and engagement.	Ignoring the human side of adoption (fear of job change, low confidence in tools, etc.).	Bringing fun and energy into onboarding and transformation moments.
Aligning success plans with both internal and client-side roadmaps—and planning for changes ahead.	Letting tooling decisions be driven by CS teams without cross-functional input or support.	Using structured feedback to improve tools, playbooks, and customer processes.

Building strong foundations through change management and success planning is essential, but how do we scale that success across an entire customer base? The answer lies in leveraging community, automation, and structured playbooks. 

Communities, Playbooks, Automation, and Customer Engagement

In this session moderated by Sally Stoewe, organisations are turning to digital strategies to deliver consistent, scalable experiences across growing customer bases. In a recent discussion moderated by Sally Stoewer, CS professionals came together to explore how digital playbooks, thoughtful automation, and clear operational frameworks are shaping the future of Customer Success.

At the heart of the conversation was a shared goal:

Build scalable, efficient, and engaging CS experiences without overburdening teams.

Here’s what we learned.

1. Scale Starts with Smart Playbooks

Digital playbooks are no longer optional; they’re essential. When you leverage automation and self-service components, digital playbooks allow CS teams to support more customers without sacrificing quality. These frameworks are most powerful when they’re adaptable across different customer segments, helping ensure that each customer receives a tailored experience, even in a digital-first environment.

“It’s not about replacing the human touch; it’s about scaling it wisely.”

2. Operational Excellence Enables Success

Success doesn’t just come from a great playbook; it comes from the team behind it.CS Operations teams play a critical role in designing and maintaining digital workflows, ensuring governance and data integrity and enabling the broader CS team to execute at scale. Meanwhile, Customer Success Managers are increasingly acting as Subject Matter Experts (SMEs), contributing insights from the field to refine and enhance digital engagement strategies.

3. Cross-Functional Playbooks Drive Alignment

The most effective playbooks aren’t created in silos. Teams are finding success by co-building playbooks with Sales, Marketing, Product, and Support, ensuring Alignment at critical journey moments, Consistency in voice and messaging and reduced duplication of effort.

Incorporating customer surveys and feedback mechanisms into automated flows also allows for real-time improvements and creates a valuable feedback loop, even in low-touch models.

4. Be Mindful of Automation Fatigue

Automation can be a double-edged sword. While it can surface important tasks, it can also overwhelm teams if not managed well.

To address this, the group emphasised:

• Effective change management—route tasks clearly via platforms like Salesforce, Slack, or your CS Platform
  
• Inclusive design—involve individual contributors in building processes to ensure buy-in and usability
  
• Deliberate capacity planning—understand bandwidth and balance triggers accordingly
  

5. Segment Strategically, But Thoughtfully

Strategic segmentation (e.g., by industry, ARR, or lifecycle stage) allows CS teams to Tailor engagement strategies, Develop specialised expertise, Foster ownership and accountability within defined segments

However, caution is needed. Poorly executed segmentation can lead to Team silos, Reduced agility and Uneven customer experiences

Start, Stop, Continue

START	STOP	CONTINUE
Designing flexible, automation-ready playbooks with cross-functional input	Overloading teams with unfiltered automation tasks	Involving CSMs and Ops in co-creating scalable processes
Segmenting customers to tailor digital strategies	Creating siloed playbooks or digital experiences	Collecting feedback through digital channels and acting on it
Capacity planning with CSP/CRM data insights	Assuming automation equals efficiency without proper routing	Focusing on operational excellence and clarity of roles

Value-based communication, Time to value & Stakeholder management

Customer Success is about articulating value, delivering impact efficiently, and managing relationships with influence and clarity. In our recent session with K. Gissberg on value-based communication, time to value (TTV), and stakeholder management, CS leaders exchanged tactical insights and strategic shifts that are driving stronger outcomes across the board.

Value-Based Communication: Beyond the Buzzwords

“Value” is one of the most used terms in CS, yet one of the hardest to quantify, especially when clients aren’t sharing the data you need. The group emphasised shifting the narrative from “delivering value” to driving continuous improvement. Asking the right questions can uncover where you’re truly making an impact. Try: “What’s possible now that wasn’t before?” Framing value around incremental, trackable gains allows teams to celebrate progress and build momentum.

Another key theme was clarity. Replace fluffy success language with business outcomes: show improvement on a slide, in a dashboard, or in the success plan. And don’t underestimate the power of storytelling, highlighting pain points that were resolved or time saved often hits harder than a vague ROI statement. Teams also discussed the challenge of shifting from tactical, feature-focused conversations to strategic impact. Tools like prioritisation matrices help bridge this gap by aligning stakeholders on what truly matters.

The bottom line? Keep asking why. At the core, most clients are seeking time or cost savings. If you know that from day one, your path to measurable success becomes much clearer.

Time to Value: Small Wins Build Big Impact

The faster your product delivers meaningful outcomes, the more likely customers are to stay engaged and succeed. Success starts at onboarding. Teams stressed the importance of setting clear ownership, realistic deadlines, and regular follow-ups. Creating small, early wins helps maintain energy and momentum. Those little dopamine hits from checking a box or achieving a milestone keep motivation high, even if the “big win” is still months away.

Professional Services can play a big role here, expediting TTV and bridging gaps between implementation and value realisation. But it all works best when backed by strong executive sponsorship and customer enablement.

Stakeholder Management: Governance, Not Guesswork

Managing stakeholders focuses more on intentional rhythm and structure. CSMs were called out as the owners of relationship governance. This includes bi-weekly operational syncs, monthly reviews of success plans, and periodic executive meetings, all documented in shared tools like Slack channels or customer portals.

Another standout tactic? Use AI agents to stay updated on changes within client organisations. Knowing when someone has been promoted, joined, or left allows you to adapt quickly and re-engage decision-makers.

When it comes to engaging new stakeholders, the simplest approach is often the most effective. Don’t pitch, rather it’s better to be straightforward and ask. A 10–15-minute call with a new exec can open doors when you ask: “How can we make your life easier?” or “What’s your vision for the next six months?” The goal is to become a partner, not just a vendor. The more you understand their world, the easier it is to align with their goals.

Start, Stop, Continue

Start	Stop	Continue
Using “continuous improvement” instead of “value” to drive meaningful conversation	Waiting for perfect data before communicating outcomes	Documenting and showcasing incremental business impact
Celebrating small wins in onboarding to speed up TTV	Leaving ownership of key tasks vague or untracked	Creating dopamine-driven progress through small, visible wins
Proactively managing stakeholder communication rhythm	Reacting only when org changes are announced	Leveraging tools like AI and Slack to stay on top of relationships
Asking new execs for their strategy and pain points	Sticking to existing champions only	Finding new paths to strategic alignment when leadership changes

For leadership only: Customer Success Processes and Metrics

During the session with Giorgia Pedenzini, we learned more about how leaders are under pressure to do more with less, drive retention, maximise lifetime value, and ensure efficient operations, all while keeping customers happy and teams aligned. In our leadership-focused session, CS heads from Charles, Leapsome, MangoPay, and others shared their candid perspectives on what metrics work, how they’re adapting internal processes, and where they see opportunities for evolution, particularly with AI, segmentation, and value realisation.

What Metrics Matter in Customer Success?

Unsurprisingly, ARR and churn/cancellation rates remain key anchors. But the conversation quickly moved into more nuanced terrain: what signals actually correlate with stickiness, advocacy, and expansion?

• NPS came under fire. Leaders like Lena questioned whether it’s the right metric at all, especially when there’s a disconnect between product experience and CS ownership. Product engagement metrics (e.g. in-app surveys or behavioural signals) often yield better traction and insight than traditional surveys sent via email.
  
• Customer Advocacy Scores had mixed results. Bruna noted that once Marketing took over the metric, its relevance to CS performance and incentives diminished. For advocacy to be meaningful, it needs to be actionable and ideally tied to both customer and CSM incentives.
  
• Health Scores remain a hot topic. Max described success in onboarding health scores with 3 simple metrics, but post-adoption health scoring remains difficult to define. CS leaders agreed this remains a key area for innovation.

Start, Stop, Continue

Start	Stop	Continue
Use product usage and behavioral engagement as leading indicators of value	Relying solely on NPS or CSAT without context	Tying onboarding to value realisation and clear goals
Multithread from day one to grow influence and reduce churn risk	Treating customer advocacy as a marketing-only KPI	Structuring feedback loops to prove outcomes
Segment renewal strategies by adoption, margin, and account potential	Pushing auto-renewals without stakeholder check-ins	Proactively engaging execs before renewal windows
Explore AI tools (e.g. Gong) to streamline onboarding and capture goals	Measuring Customer Success success only through reactive support metrics	Investing in health scoring that evolves post-onboarding

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