If you want your SaaS company to grow, renewals and upsells are key. According to McKinsey, companies with high net revenue retention (NRR) consistently outperform their competitors, growing up to 3.5 times faster. And that growth doesn’t just come from winning new customers—it’s driven by keeping the ones you already have.
But let’s be real: managing renewals isn’t easy. You have to balance personalization with efficiency, and when you’re managing hundreds of accounts with different renewal dates, keeping conversations personal can feel almost impossible.
Renewals are also where most customer churn happens. Sometimes, a customer decides to leave just before their renewal date, and you’re left wondering what went wrong. Other times, there were early signs—but if you didn’t catch them, you missed the chance to act.
To prevent churn, you need to build stronger, more meaningful relationships. But how do you do that at scale without burning out your team? That’s where AI can help. By automating renewal reminders, spotting upsell opportunities, and predicting churn risks, AI gives you the tools to engage customers at the right time, in the right way.
In this article, you’ll learn:
- Common roadblocks in managing customer renewals
- How to use AI to improve your renewal process.
- Best practices for using AI to strengthen your renewal strategy.
Common Challenges in SaaS Renewal Management
Renewals shouldn’t be viewed as mere transactions. They’re pivotal moments that shape long-term customer relationships. Here’s where customer success teams often get stuck:
1. Spotting Churn Signals Early
It’s hard to distinguish between a quiet but satisfied customer and one slipping away.
Gartner’s Digital Markets report reveals that 60% of software buyers experience regret after a purchase, often due to unmet expectations or poor onboarding. Many of these buyers also cite "mismanaged expectations during implementation" as a key driver of churn.
Without proactive tracking of customer sentiment and usage patterns, customer success managers (CSMs) may only catch issues once they’ve snowballed.
2. Finding the Right Time to Engage
Another challenge is timing. When is the right time for a renewal conversation? Timing plays a significant role in renewal success, with early but personalized engagement often leading to better outcomes. However, not every customer fits the same timeline.
Some benefit from a touchpoint two quarters out, while others prefer a check-in closer to the renewal date. Companies that fail to tailor renewal touchpoints based on customer goals may unintentionally frame renewals as sales transactions rather than value discussions. And that’s a no-go zone.
3. Scaling Personalized Engagement
Then, we have the issue of personalization. The more accounts you manage, the harder it becomes to maintain a personal touch. It almost becomes impossible to manually track every customer’s usage, sentiment, and renewal window. This leads to reactive rather than proactive engagement—and that’s a risky game when your net revenue retention depends on delivering continuous value.
As per SaaS Capital data, companies with annual contract values (ACVs) above $25,000 see a median net revenue retention (NRR) of at least 103%, with top-quartile performers surpassing 118% to 120% for contracts over $100,000. This trend underscores how higher-value contracts drive stronger customer retention, fueled by upsells, cross-sells, and proactive engagement strategies that deepen customer relationships.
So, your challenge boils down to this: how can your customer success team (or renewal team) stay efficient while delivering personalized, proactive touchpoints across hundreds of accounts—without burning out? That’s where AI can make all the difference!
How to Use AI for SaaS Renewals and Upsells
Renewals and upsells are pivotal moments that can grow or shrink your bottom line. But you’ll agree there are way too many variables to track across hundreds of accounts. That’s the reason why churn signals often slip through the cracks.
AI tools help by surfacing insights, automating workflows, and ensuring your team stays focused on what matters: building strong customer relationships and driving growth.
1. Surfacing Important Signals
As I mentioned above, one of the hardest parts of renewal management is spotting churn risk early. Customers don’t always send clear signals—they might even give positive feedback while decreasing product usage.
Another problem is that customers can express dissatisfaction through multiple channels. They might send a Slack message, drop a quick email, or raise a support ticket. Support tickets, in particular, are important here because they are often a blind spot for sales and customer success teams because they are managed by the support team.
AI changes that by continuously analyzing data such as CRM fields, sales calls, Slack messages, and support tickets. It can then assign churn risk scores based on patterns or flag specific signals so your team knows which accounts need attention.
For instance, our tool, Momentum, pulls all these AI signals and auto-delivers them to relevant stakeholders via Slack DM or channel.
Our CEO, Santiago, recently shared on LinkedIn how Momentum does this in a bit more detail. 👇
2. Proactive Notifications and Automated Reminders
No CSM should have to live by calendar reminders alone. With Momentum’s Notifications, you never miss key touchpoints.
With scheduled paths, you can send automated reminders to Slack channels or DMs based on key Salesforce events, such as a QBR date or contract renewal milestone.
For example, you can configure notifications to remind account executives to check in seven days after an important meeting. If the opportunity status updates, the notification automatically cancels—keeping the workflow clean and preventing unnecessary follow-ups.
3. Centralized Account Management with Account Rooms
Renewals often require input from multiple teams—customer success, sales, finance, and even product management. But when these teams operate in silos, communication gaps can lead to misalignment, missed opportunities, and a less-than-ideal customer experience.
That’s not an issue with Momentum. We’ve designed Momentum’s Deal and Account Rooms to centralize everything—customer history, renewal timelines, meeting notes, support tickets, and feedback—into a shared workspace directly within Slack. This gives everyone involved in the account, from CSMs to finance leads, real-time access to the same information.
This visibility means fewer back-and-forths, no more digging through emails or spreadsheets, and a faster, more collaborative approach to renewal and upsell motions.
4. AI-generated Summaries for Informed Decision-Making
When your customer success manager or whoever is responsible for renewals jumps on a call with the customer, there’s going to be a lot of things discussed. You simply do not have time to record all of that information. And thanks to Momentum’s AI call summaries, you don’t have to!
Momentum takes notes for you, so you don’t have to remember every little detail from your renewal calls. It then summarizes them into actionable data in your CRM and Slack, which can be shared with your team in real time. So, instead of getting bogged down in note-taking, your team can focus on checking in at the right time and securing that renewal.
5. Personalized Customer Engagement
AI can certainly do a great job of surfacing essential signals. It can also help you personalize your engagement with about-to-renew customers.
When it’s time to renew, customers start evaluating your solution. They look at things like:
- How well was it used?
- Where did your product fall short?
- How quickly did you resolve technical issues?
- Did the value match the cost?
While most customers don’t walk away unless your product is a total letdown, you must address potential churn risks. That means sitting down with your customer and working through any doubts or concerns.
That’s when you need to be ready to jump on a call, listen carefully, and work toward a win-win solution. After those calls, thoughtful follow-up emails are crucial. But when you’re juggling multiple renewals, creating personalized, insightful follow-ups for each can become overwhelming.
That’s where Momentum’s follow-up feature makes a difference. It automatically generates personalized, context-rich emails right after your calls by pulling key insights from the conversation. You can review the drafts in Slack or Gmail and send them off in just a few clicks—saving you hours each week.
SaaS Renewals Best Practices
Having outlined the ways AI can support your SaaS renewal management, here are some best practices to follow for maximum success.
Start Small, Scale Strategically
Rather than overhaul everything immediately, start by automating small but impactful tasks like renewal reminders and meeting summaries. Once the team sees the time savings, you can scale to more complex workflows like predictive upsell recommendations and personalized messaging.
Integrate AI with Existing Tools
Your team shouldn’t have to jump between platforms. Ensure your AI solutions integrate with tools your team already uses, like Slack, Salesforce, and Zendesk. This keeps processes efficient and, of course, increases adoption by meeting your team where they work.
📖 Related Read: 8 Tools You Need in Your B2B Sales Tech Stack
Personalize, Don’t Automate Blindly
AI can handle data-heavy tasks, but personalization should remain at the core of your customer interactions. Instead of sending generic communications, use AI insights to tailor your messaging to customer needs.
Wrapping Up
Renewals are the result of consistent value and strategic guidance. By using AI to stay one step ahead, your team can focus less on admin and more on building deeper partnerships, leading to bigger wins.
See how Momentum can streamline your post-sales process, surface key insights from sales calls, emails, SMS, and support tickets, and keep your team ahead of every renewal. Chat with our team today so we can get you onboarded.