Lisbon CSS Roundtable: A Community Ready for the Future of AI-Powered Service

# CSS Executive Roundtable

Organized by SuccessLab • Hosted by OutSystems

December 1, 2025

Last week’s CSS Roundtable in Lisbon marked an important moment. Local leaders showed that this community is not trying to keep up with the global conversation. It is already contributing to it. The discussion was thoughtful and fully aligned with what we are hearing in the US and across Europe.

What emerged was a distinctly voiced by warm hospitality, practical judgment, and a human-first approach to service and technology.

1. AI as Real Transformation

One of the opening comments captured the tone for the day:

“Everyone experimented. Now our CEOs and CFOs want to see real value.”

Leaders in the room clearly understood the gap between AI potential and AI proof. They are moving past superficial fixes and focusing on genuine transformation. That means new engagement models, new solutions, and new ways to demonstrate value throughout the customer journey.

Our host, Cristina Roque Lino, VP of Global Professional Services at OutSystems, offered a clear and candid view of how her organization is approaching this shift. Professional Services, Support, Success, Product, and the entire company are aligning around shared AI programs and learning to work beyond traditional boundaries.

2. Two Market Realities, One Intense Pressure

We explored the widening contrast between two types of companies:

AI-native hyper-scalers

High-velocity experimentation

Minimal concern for cost

Valuations far ahead of revenue

Hiring and scaling without friction

Transformation-stage incumbents

Need to modernize while protecting margins

Pressure from boards for AI-level speed

Customers expecting AI-native experiences

Tension between speed, cost, and governance

The leaders described this tension as follows:

“We are expected to move like AI-native companies while delivering profitability and governance at the same time.”

3. Customer Expectations Have Shifted Quickly

A story from a recent global CAB captured the new customer mindset:

“Stop giving me prescriptive journeys. I want adaptability. My outcomes change as my business changes.”

Across the table, people nodded. We heard examples of customers who:

Seek AI-native experiences even if they do not fully trust AI yet

Reject AI until a regulator or competitor forces it ahead

Prefer digital self-service

Prefer high-touch human guidance

Buyer preferences are fragmenting. Engagement models must adapt.

4. Value Realization Is the Hardest Problem to Solve

We returned repeatedly to the distinction between value selling and value realization. Most companies can define value at the start of the journey. Far fewer can prove it consistently over time.

AI is emerging as the missing link. It can help translate telemetry, sentiment, usage patterns, architecture, and business outcomes into insights that are credible at renewal and throughout the lifecycle.

One comment captured the challenge nicely:

“Value selling is clear. Value realization is a different animal.”

5. Customer Success Is Evolving Quickly

We discussed whether Customer Success (CS) is becoming more technical. The group was split, but the direction was clear:

CS must become more consultative

CS must become more AI-fluent

CS needs a stronger voice with Product

Technical literacy is becoming a differentiator

A memorable comment summed it up:

“If CS ran the whole company, we would go bankrupt. If Sales ran it, customers would not renew. The future requires both working together.” Lisbon understands this balance intuitively.

6. How Product, Engineering, and Support Should Align

We explored different organizational models. Some companies place Support under the same leader who oversees Product and Engineering, while others keep it customer-facing.

The consensus: structure matters less than alignment. Support, Success, and Services should remain close to the customer, while working in lockstep with Product and Engineering through shared KPIs and shared ownership of outcomes.

This is not a reorganization. It is a rethink of how teams work together.

7. Governance, Security, and Compliance Are the Next Frontier

Security surfaced as a central

theme, especially in light of recent cyber incidents that have raised expectations on both vendors and customers. Leaders voiced security concerns and spoke about:

New attack surfaces introduced by AI

The need for trust and governance as differentiators

Customers want AI, but want to see the guardrails first

Regulators lagging behind industry reality

One cybersecurity leader captured the urgency well:

“AI allows us to penetrate cloud applications faster than ever. Customers need AI, but they need proof it is safe.” Trust is as important as innovation.

8. Rethinking Case Deflection

While many companies celebrate case deflection as an AI win, our leaders challenged the idea and raised thoughtful questions:

Are we losing opportunities to learn?

Are we missing moments to identify new use cases?

Are we reducing cases but not reducing root causes?

The goal is not fewer tickets. The goal is fewer problems, better products, and stronger relationships. AI should bring the customer closer, not push them further away.

9. The Power of Human Connection

One of the most encouraging themes was the renewed value of face-to-face engagement. Leaders shared examples of:

Value Acceleration Days

Architecture and roadmap reviews

Onsite diagnostics

Deep consulting conversations

AI can enhance these moments, but it cannot replace them. The future is human, digital, and AI working together.

Gratitude

A heartfelt thank you to:

Cristina Roque Lino, Miguel Almeida, Paulo Garcia, and the OutSystems team for their warm and open welcome.

Sofia Barbosa, Chief Customer Officer at BMC Software, for championing the idea early and elevating the discussion with her depth of experience and perspective.

All the leaders from Support, Success, Services, Product, People, Cybersecurity, and Operations shared their experience and insight.

I look forward to returning to Lisbon and continuing to learn and share with this community. It is clear that you are ready to shape the future of CSS, not simply respond to it.

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