Managing reluctance from SaaS customers who are hesitant to upgrade is a specialized aspect of customer success and sales. 

While this reluctance can be a hurdle, it also offers a chance for meaningful engagement and problem-solving. 

In this guide, we’ll delve into effective strategies for addressing this specific type of customer objection and examine the challenges you might face.

Strategies for Tackling Reluctance to Upgrade

Active Listening

Begin by attentively listening to the customer’s reservations about upgrading. This not only shows respect but also helps you understand the underlying issues. Active listening goes beyond the words; it involves grasping the sentiments and motivations behind them. For instance, a customer success manager listens intently when a user expresses concerns about the new features being too advanced.

Clarify the Reluctance

To tackle the issue effectively, you need to understand it fully. Pose questions that help you get to the core of the customer’s reluctance. This could involve asking them to elaborate on their concerns about the new pricing model or the features they find unnecessary.

Acknowledge the Hesitation

Recognizing the customer’s hesitation shows empathy and can defuse tension. It also paves the way for a constructive conversation. For example, acknowledging that the new pricing model may initially seem more expensive but explaining the added value it offers.

Present Evidence

Once you’ve grasped the reluctance, counter it with solid evidence like user testimonials, case studies, or ROI calculations. This not only adds credibility but also helps in alleviating the customer’s concerns. For instance, sharing success stories of other customers who benefited from the upgrade.

Suggest Alternatives

Sometimes, customers are unaware of different plans or features that could suit them better. Offering these alternatives can show your willingness to adapt your solutions to their specific needs. For example, suggesting a staggered upgrade plan that eases them into the new features.

Be Transparent

If you can’t immediately address a concern, honesty is the best policy. This can build trust and set the stage for future interactions. For example, admitting that a certain feature is in the development pipeline but not yet available.


After discussing their reluctance, always follow up to show that you take their concerns seriously. This could be a summary email or a scheduled call to discuss any remaining questions.

Know When to Step Back

Sometimes, despite your best efforts, the customer may not be ready to upgrade. Knowing when to respectfully disengage is crucial. In such cases, leave the door open for future discussions.

Challenges in Handling Reluctance to Upgrade

Emotional Barriers

Customers may have emotional reasons for not wanting to upgrade, such as comfort with the current version. Addressing this requires emotional intelligence and rapport-building.

Multiple Decision-Makers

In a SaaS environment, various stakeholders like IT, finance, and end-users may have different views. Balancing these differing opinions and the specific business goals of all groups is key.

Complex Concerns

Some customers may have intricate issues like compliance or integration concerns that can’t be resolved quickly. These require a nuanced approach and possibly consultation with experts.

Resource Limitations

Especially in smaller SaaS companies, limited resources can make it challenging to address every concern. Prioritizing the most significant issues becomes crucial.

Additional Strategies for Encouraging SaaS Customers to Upgrade

1. Limited-Time Promotions

  • Idea: Offer a limited-time discount or added features for customers who decide to upgrade within a specific timeframe.
  • Real-Life Example: Dropbox occasionally offers a 20% discount for the first year when existing users upgrade to Dropbox Plus or Family plans.

2. Feature Teasers

  • Idea: Allow customers to experience premium features for a short period, giving them a taste of what they’re missing.
  • Real-Life Example: Adobe Creative Cloud often provides a 7-day free trial of premium features, enticing users to upgrade for continued access.

3. Customer Success Webinars

  • Idea: Host webinars that not only provide value but also showcase advanced features available in upgraded plans.
  • Real-Life Example: HubSpot frequently hosts webinars that subtly introduce advanced analytics and automation features, available only in their premium plans.

4. Personalized Upgrade Recommendations

  • Idea: Use customer data to offer personalized upgrade suggestions based on their usage patterns.
  • Real-Life Example: Spotify analyzes your music listening habits and occasionally suggests upgrading to Spotify Premium to enjoy features like offline listening and no ads. They use call-to-action buttons to direct listeners to their subscription page.

5. Loyalty Programs

  • Idea: Implement a loyalty program where points can be earned and redeemed for upgrades.
  • Real-Life Example: Salesforce has a loyalty program that allows customers to earn points through various activities, which can then be redeemed for upgrades or other perks like virtual escape rooms or conert tickets.

6. Social Proof

  • Idea: Leverage testimonials and case studies from customers who have benefited from upgrading.
  • Real-Life Example: Slack showcases testimonials from companies that have moved from their free to paid plans, emphasizing the increased productivity and enhanced features.


Managing reluctance from SaaS customers to upgrade is a nuanced task that requires a blend of strategic thinking and emotional intelligence. By adopting these strategies and being mindful of the challenges, you can transform reluctance into opportunities for customer engagement and retention. Remember, the ultimate goal is not just to facilitate upgrades but to foster long-term, trusting relationships with your customers.