Inspired by Doing It For Retention – Episode 011, Customer Success, AI and PLEO. Available to watch and listen today.
Artificial intelligence is reshaping Customer Success at a pace few predicted. Dashboards auto-update. Health scores generate themselves. AI summaries pull three months of customer behaviour into a neatly packaged paragraph.
It all sounds wonderfully efficient. But efficiency isn’t retention.
And that’s the central theme running through this conversation with Craig Jackson, one of the leaders behind Customer Success at PLEO. While AI is creating new possibilities, Craig’s experience shows that empathy, intuition, and human connection aren’t just still relevant — they’re becoming more important.
This episode explores the space where technology ends and people begin. And it’s in that gap where the best Customer Success teams are differentiating themselves.
The Foundation: Customer Success Is Still a Human Discipline
Craig’s path into Customer Success gives him a unique vantage point. He’s held roles in sales, leadership, and operations, which gives him a practical view of how commercial outcomes are built. That background matters — because it grounds his perspective on AI in something many teams forget: Customer Success is ultimately about people.
Across all the growth, organisational changes, and new tools at PLEO, one thing has remained constant for his team: the belief that customer relationships only thrive when they’re understood at both a technical and emotional level.
AI can help with the technical side. But the emotional side still belongs firmly to humans.
Where AI Accelerates Customer Success
PLEO’s AI use cases are deliberate rather than experimental. Instead of chasing trends, the team evaluates one question: Where are we losing time that could be better spent with customers?
This has led to some genuinely meaningful improvements. AI now pulls instant summaries of customer engagement, identifies behavioural patterns, and helps teams respond to internal queries in a fraction of the time. These changes free up hours each week — not to reduce headcount, but to give CSMs more space to think, reflect, and build stronger relationships.
The technology supports the work rather than replacing it. It fills the gaps that data can fill, and leaves the rest to humans.
Where AI Falls Short
The challenges begin when AI tries to interpret meaning rather than just surface information.
AI can show a customer’s usage trend dropping. It can highlight slower response times. It can flag unusual behaviour. But it can’t understand why those things matter, or what emotional nuance sits behind them.
A customer might reduce usage because they’re restructuring, changing priorities, or onboarding a new leader. None of that shows up in a dashboard. That insight only emerges through conversation, curiosity, and empathy.
This is where Craig’s team leans into human judgement. They treat AI as an early signal, not a decision-maker. It points them in the right direction, but it doesn’t replace relationship awareness.
Rethinking Customer Health With Humans at the Centre
Traditional customer health scores often rely on internally assumed metrics. They measure activity, but rarely sentiment. They reflect data, but not the relationship.
By embracing AI-driven analytics, PLEO has been able to identify risk indicators that humans may miss. But instead of relying on these signals as the final answer, the team uses them as prompts. They ask better questions, reach out sooner, and tailor their approach with greater confidence.
It’s a shift from reactive firefighting to proactive partnership — and AI is the catalyst, not the solution.
Why Empathy Is a Competitive Advantage
The more automated the industry becomes, the more valuable human connection becomes.
Customers who feel understood stay longer. Teams who feel empowered perform better. Leaders who encourage emotional intelligence build cultures that retain people and customers alike.
AI can drive consistency and scale, but empathy shapes loyalty. The two don’t compete — they complement each other when used intentionally.
Craig’s approach shows that the future of Customer Success isn’t technology replacing people. It’s technology giving people more time to do the work only humans can do.
Final Thoughts
AI can tell you what happened.
Only people can understand what it means.
The teams that outperform over the next decade won’t be the most automated — they’ll be the ones who blend intelligence, intuition, and empathy into a coherent customer experience.
Technology may drive efficiency.
But empathy still drives retention.
