When I assess the health of a complex account with multiple stakeholders, I start with a principle I have carried through my entire career: know your customer. It sounds obvious. In practice, most organizations only apply it halfway.
For me, assessing customer health consistently comes down to two dimensions: metrics and relationships.
Metrics: Looking Beyond the Shared Scorecard
It is not enough to look only at the performance indicators inside the relationship. I also look at the customer’s broader financial context when that information is available. Changes in funding, revenue pressure, cost constraints, or external risk often show up as early warning signs long before they appear in operational KPIs. By the time a metric moves, the risk has usually been building for months.
Relationship Health: Three Layers
On the relationship side, I assess health across three connected areas.
The customer’s organization. Structure, decision flows, and roles. Who operates, who influences, and who decides.
The holistic relationship. Where the partnership sits today: supplier, partner, or trusted advisor.
The individual relationships. Both the transactional layer (opponent, gatekeeper, neutral, supporter, champion) and the emotional layer (day to day business casual versus strictly professional).
Together, these give a far more complete and forward-looking view of account health than metrics alone. They get to the real drivers of stability, risk, and long-term growth.
Alignment Starts in Sales, Lives in Customer Success
Know your customer only works if it connects to alignment at every level of the partnership. In my experience, that alignment is often established during the sales process. It becomes something living once Customer Success is involved, which is why I believe CS needs a seat at the table during the sales cycle itself, not after the contract is signed.
Customer Success is where alignment gets reinforced, tested, and reshaped as the customer’s organization, priorities, and leadership change over time.
Bottom Up or Top Down: There Is No Single Answer
One of the harder judgment calls in maintaining executive alignment is whether to work bottom up or top down. I don’t believe there is one right answer. This is exactly where knowing your customer matters most.
Understanding the customer’s decision-making culture and the influence of key players tells you which path to take, and when to shift it. In some accounts, strong operator advocacy builds enough momentum to re-engage executives. In others, executive sponsorship has to be rebuilt first before anything moves at the operator level. Knowing which lever to pull, and when, is often the difference between a stable partnership and one that quietly drifts at risk.
Governance and Disciplined Execution
Once alignment and expected value are defined, they need to be reinforced through disciplined execution. I do this by building relationships at every level of the customer organization, supported by joint strategic planning and regular business reviews.
Those reviews are anchored in clear metrics and scorecards tied directly to the customer’s strategic and financial priorities. When value is consistently measured, communicated, and reinforced this way, it builds shared accountability, strengthens executive confidence, and creates a strong foundation for renewal and expansion.
Where Renewals Actually Break
I tend to view Customer Success through the lens of structural engineering. Any durable structure depends on strong footings and a solid foundation. In Customer Success, the footings are a culture of customer centricity. The foundation is the trust earned through consistent delivery and follow-through. Without both, it is very difficult to build anything sustainable on top.
When renewals or expansion stall, the cause usually traces back to cracks in one of those two layers. The customer may be using the platform, but they don’t feel supported, heard, or confident in the partnership. It is rarely a single metric or feature gap. It is a breakdown in how the organization shows up for the customer and reinforces trust over time.
My approach to unblocking renewals starts by strengthening those fundamentals first. Once customer centricity and trust are solid, renewal and expansion stop being something you have to force. They become a natural extension of the relationship.
Know Your Audience for ROI
This comes back to knowing your customer, and more specifically, knowing who inside that customer you need to speak to about ROI. The message only lands when it is tailored to how each group defines and measures success.
Operational leaders care about time saved, process efficiency, and scalability. IT leadership cares about platform stability, security, and reduced risk. When the ROI narrative is built for the audience in front of you, the value of the relationship becomes clearer, more credible, and easier to defend over time.