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Inside Customer Success at LearnUpon: Driving Customer Impact
Customer Success in SaaS is changing. As technology takes on more of the transactional work, the role of the Customer Success Manager (CSM) is increasingly about understanding the bigger business picture, navigating complexity, and connecting customer outcomes with long-term value.
As a Customer Success Manager at LearnUpon, Zach Raynor works across a portfolio of enterprise customers, partnering with stakeholders across their organisations and bringing together expertise from teams across LearnUpon. In this conversation, he shares what great Customer Success looks like today, how commercial accountability fits into the role, and why judgement, curiosity and the ability to connect the dots matter more than ever.
Customer Success has evolved a lot in SaaS. What does being a great CSM look like today?
Customer Success has always been about helping customers see value in the product, and that’s still important. But I think the role has become much broader.
A great CSM needs to understand both what matters to the people using LearnUpon day to day and what the wider business is trying to achieve. That starts with trust — genuinely caring about the customer’s challenges and becoming someone they see as part of their extended team.
From there, the conversation naturally moves beyond product usage. You can start asking where the business is going, what matters most to them, and how LearnUpon can support those goals over the longer term.
How do you move from understanding how a customer uses LearnUpon to understanding what really matters to their business?
You have to think at a couple of different levels at the same time. You need to understand the team you work with most closely: what they’re trying to achieve, where they’re running into friction and what success looks like for them. But you also have to zoom out. What does the company actually do? Who are their customers? What drives revenue? Where are they trying to reduce cost or risk?
In enterprise accounts, different stakeholders will naturally care about different things. An admin team might be focused on reporting, integrations or making a workflow easier to manage, while senior stakeholders may be thinking further ahead about AI, personalization or broader learning strategy. Part of the CSM’s role is understanding those different perspectives and connecting them back to the bigger picture.
You don’t learn all of that in one meeting. It comes from listening, asking the right questions and building your understanding over time. Eventually, you start connecting what’s happening inside LearnUpon with what matters to the business as a whole.
Customer Success has a commercial side too. How do you balance customer outcomes with renewals and growth?
For me, those things aren’t really separate. Yes, the role has commercial accountability. We want to retain customers and grow our partnerships with them. But the strongest commercial outcomes come when the customer is genuinely getting value and believes in the partnership.
Because the CSM often knows the customer and the context around their account extremely well, we also have an important role internally. Sometimes that means advocating for a particular resource, bringing in the right expertise, or helping the business understand why something matters to that customer.
If we make good decisions for the long-term health of the partnership and keep the customer’s outcomes at the centre of those decisions, retention and growth tend to follow.
As AI changes both learning and the CSM role, where do you think human judgement becomes most important?
On the customer side, we’re already seeing conversations shift towards data, personalization and how learning fits into the wider technology ecosystem. Integration conversations used to be more transactional — we want this API to trigger this action, for example. Now customers are thinking more about how data can move between systems to create a more connected experience, where learning fits naturally into someone’s flow of work.
At the same time, AI is making parts of the CSM role easier. It can help draft an email or get an EBR deck started. But so much of Customer Success is about judgement.
You’re constantly taking in information from the customer, Product, Solutions, leadership and other teams across the business. Those perspectives don’t always perfectly align, so you have to understand the context, work out what really matters, and turn all of that information into a clear path forward.
We talk a lot in L&D about keeping the human leading the loop. I think the same applies to Customer Success. Technology can make us more effective, but the CSM is still the person connecting the dots and applying the judgement behind what happens next.
What does it take to thrive as a CSM at LearnUpon today?
First, you need to be a strong project manager. You’re managing multiple customers, stakeholders, priorities and initiatives at the same time, so you need to keep things moving.
You also need to be able to influence internally. That doesn’t mean having formal authority — it means being able to explain why something matters, make a strong case for an account need and bring the right people together.
That cross-functional element is a big part of the job. In any given week, you might be preparing for an EBR, working through a renewal, responding to an unexpected customer need or partnering with Product, Solutions, Marketing or CX Leadership on an account challenge.
Another important skill is synthesis. You might be hearing one thing from a Solutions Architect, something else from the customer, another perspective from Product and a commercial consideration from the business. You have to turn all of that into a clear recommendation, project brief or conversation with the customer.
And finally, I think kindness matters more than people sometimes give it credit for. Customer Success is ultimately a people role. You have to genuinely want to help your customers and your teammates succeed.
For me, that combination — relationship-building, commercial awareness, managing complexity and turning a lot of different information into action — is what makes the role so interesting right now.
Interested in joining Zach on an exciting career journey? Check out LearnUpon’s latest list of open positions here.