5 Customer Retention Secrets for Weathering Economic Challenges


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With a potentially rocky economic road ahead, many organizations might be adjusting budgets now for products and services in 2023. How do you cement your company’s place on a customer’s “must-have” list? A great customer experience (CX) and personal relationships make all the difference.

Preparing your team now for potential changes in the coming months could mitigate churn risk, and solidify your most important customer relationships for years to come. Here are some tips for how to navigate potential retention obstacles, even in the toughest economy.

1. Reiterate your customers’ goals (not your own)

A big part of retaining customers is understanding how they perceive return on investment (ROI) for your product or service. Many companies make the mistake of focusing on their own internal benchmarks of what ROI should look like, when in reality your customer doesn’t care about your internal health score. In a tough economy, it’s critical to reiterate to customers why they purchased, and focus on your key value proposition to showcase ROI.

The exact ROI will depend on the customer. Understanding the metrics that impact them the most starts early in the discovery process. For example, rather than benchmarking meetings alone, a sales team may be more interested in how many of these meetings generate revenue or conversions. Locking in on the right ROI data positions your solution as a must-have, versus a nice-to-have.

Next, it’s critical to understand where the customer wants to be in the future, and align your current product and future roadmap with these priorities. You may choose to partner with your product team at applicable times to make sure these future needs are addressed. For example, give valued customers a sneak peek at designs, or allow them to provide feedback on upcoming features that matter most to them.

2. Lead with empathy and understanding

Layoffs are increasing and how you show up in these customer calls matters more than ever. It’s critical to lead with empathy as it can be scary and emotional for the remaining team members.

Going straight to a retention play versus taking the time to understand how your key contacts are doing is a miss. Once you acknowledge and empathize, then set your focus on saving the account. Key questions to ask yourself: How can you rally around them and support them? How can you work on a strategy that meets the needs of both the business and the remaining team?

Instead of leading with contractual conversations, focus on how your solution has helped them achieve their most critical business outcomes (as mentioned above) and get curious on how you can help them through this next chapter. This gives an opportunity to build an authentic, human connection and increases the likelihood of a long term partnership of future winback.

3. Celebrate key milestones and small victories

Rule of thumb: take the opportunity to highlight a win! Whether a customer has booked their thousandth meeting, or closed a key deal – it’s important to celebrate important milestones. So how do you gather key milestones? Ask your customer what an initial win would look like during onboarding or in the next 90 days, and work to make it happen! You can also highlight internal stats on utilization, feature adoption, and more.

For instance, our team at Calendly sends celebratory emails highlighting small wins. Every customer and email is different, but we do love a good gif to keep the mood light and fun. Customers typically respond back to these emails, which provides a great engagement point. Some companies also add in-product moments of surprise and delight (think Asana’s celebratory unicorn animation that appears when you check an item off your to-do list). Either way, these moments keep your product’s ROI and strong partnership top-of-mind for customers.

4. Engage power users

Having a single or a few champions within an organization is good start, but it may not be enough – especially if a company undergoes layoffs or turnover. Mitigating this risk means expanding your relationships by going wide within the organization. One pro tip is to engage with your power users. By leveraging product data, you can easily understand who is using your product the most, and how they’re using it.

For example, if adoption isn’t as high as you’d like it to be, reach out to the top two users to understand how they are finding success. Take this engagement as an opportunity to celebrate them, ask what’s one feature they could not live without, showcase features they don’t know about, or partner with them on suggestions to drive further team adoption. One idea we’ve seen success with is having them lead a short prescriptive training in a team meeting or record it and send it through Slack!

5. Be flexible on terms

If you find that your customer needs to cut back, being flexible might mean the difference between contraction and churn. The companies that understand and are empathetic to contraction stand the highest chance of winning back customers. As the economy rebounds or their situation changes, they’ll remember how you helped them and want to resume the partnership.

Don’t be afraid to get creative while knowing the limitations of your business. Work with customers to understand who remains on the team and what their needs are to mitigate additional risks. For example, is there term flexibility to move from an annual to monthly contract? Can they reduce licenses and move to an elevated tier with great functionality to support them? How can you incorporate services to help increase adoption and/or help the customer meet key ROI goals?

Weathering challenging economic times is never easy; it’s important to keep your customer relationships strong and your product’s value clear. Start with Human and Find A Way are two Calendly values that we focus on. In times of need, we encourage everyone to remain empathetic and flexible to customers’ needs, while reinforcing the ROI provided. How we show up matters; doing the above well leads to fostering long-term, loyal customer relationships and brand advocates.

Katie Christian
Katie Christian is a customer-centric revenue leader who's passionate about serving and scaling businesses and teams. Today, Katie leads as Head of Customer Success at Calendly one of the fastest-growing product-led growth companies. She's been named a Top 40 Customer Success Influencer and a Top 50, Sales Women to Watch.


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