Engaging At-Risk Customers

In this episode of CSin15, Jason and Chris explore how to effectively engage at-risk customers. They discuss the key indicators that signal an account may be at risk, including decreased communication, reluctance to expand relationships, and usage decline. The conversation also covers best practices for addressing risk head-on, from asking direct renewal questions to creating a structured action plan. They share strategies for engaging executives, knowing when to escalate concerns internally, and balancing persistence with maintaining a strong customer relationship.

Key Takeaways:

• Recognize the Warning Signs Early – Pay attention to changes in customer engagement, product usage, and stakeholder turnover. If something feels off, investigate further.

• Be Direct About the Renewal – Instead of making assumptions, ask customers upfront if they would renew today and what would need to change for them to stay.

• Engage Multiple Stakeholders – If a champion is limiting access to other decision-makers, it could indicate a deeper issue. Expanding relationships within the org is key.

• Communicate Proactively & Escalate When Needed – Keep internal teams informed, develop a clear risk-mitigation plan, and document efforts to ensure alignment.

Recognizing At-Risk Customers: Real-Life Scenarios

Identifying risk isn’t always as simple as noticing a drop in product usage or unresponsive contacts. Sometimes, the warning signs are more nuanced. As Jason shared in the episode, one major red flag is when a champion limits your access to other stakeholders. In one example, he recalled a customer who refused to involve additional team members in a renewal discussion. This reluctance often signals internal misalignment or dissatisfaction—key indicators that an account is at risk.

Another example is when a customer’s engagement slowly declines over time. If a once-responsive contact starts canceling meetings, delaying responses, or showing hesitation in discussing future planning, it’s a sign that something is wrong. As Chris mentioned, even subtle behaviors like ignoring expansion discussions can indicate trouble brewing behind the scenes.

Key Questions to Ask At-Risk Customers

Being direct about risk is crucial. Instead of making assumptions, CSMs should ask clear, concise questions to get an honest read on the situation. Some effective questions include:

• “If your renewal was today, would you feel confident signing?” (Jason’s go-to question for uncovering risk.)

• “Are there any internal concerns about our platform that haven’t been raised?”

• “What specific outcomes do you need to see from us in the next few months to renew?”

• “Are there any competitor evaluations happening that we should be aware of?”

By asking these types of questions, CSMs can encourage transparency and get ahead of potential churn risks before they escalate.

When to Escalate an At-Risk Account Internally

As Chris emphasized in the episode, the best time to escalate an at-risk account is earlier than you think you should. Internal teams don’t like surprises, and last-minute escalations before renewal can limit your options. Consider escalating when:

• A key contact becomes unresponsive for multiple weeks.

• A competitor is introduced and conversations start shifting.

• The customer expresses doubts about ROI and requests unrealistic improvements in a short timeframe.

• You identify a blocker within their team that could delay progress.

When escalating, it’s also important to involve the right people. Chris recommends activating a “village” approach, bringing in AEs, managers, or even executives to multithread within the customer’s organization.

Action Plan Template for At-Risk Customers

Once risk is identified, it’s critical to build a clear plan. Jason shared his structured approach for managing at-risk accounts, which includes:

1. Define the risk factors. Is it low usage, lack of executive buy-in, or something else?

2. Develop an engagement strategy. Increase touchpoints, reestablish executive alignment, or focus on quick wins.

3. Align with internal teams. If necessary, loop in leadership, AEs, or product teams to strengthen your position.

4. Set realistic goals and timelines. As Chris pointed out, if a customer expects to go from 1.5X ROI to 10X ROI in four months, push back and establish achievable targets.

5. Track progress and adjust. Keep a record of actions taken to show your efforts, even if the outcome isn’t a successful renewal.

Final Thoughts

Managing at-risk customers is a skill that requires proactive communication, strategic engagement, and the ability to escalate when needed. As Jason summed up, “Do it early, be willing to be annoying, and own it all.” If a customer churns, the worst situation is one where there’s no record of what was done to save them. Taking these steps ensures that CSMs have the best possible chance of turning an at-risk account into a long-term success.

For more insights, listen to the full episode or check out our previous discussions on managing your book of business.