The Art of the Upsell

Upselling and cross-selling are essential for B2B SaaS companies aiming to maximize customer lifetime value and drive sustainable growth. Yet, there’s a fine line between adding value for customers and coming off as too sales-driven.

When done correctly, upselling strengthens customer relationships, meets their evolving needs, and increases their loyalty to your product. But for this approach to be successful, it’s crucial to focus on customer needs, highlight the value of your solution, and build trust every step of the way.

This article explores strategies to make upselling and cross-selling feel organic, value-driven, and customer-centric, leaving your customers feeling supported, not sold to.

Understanding the Customer-Centric Approach to Upselling

Before diving into strategies, it’s important to understand why a customer-centric approach to upselling is effective. Traditional hard-sell tactics can feel pushy and transactional, which may cause customers to view upsells with suspicion or skepticism. In B2B SaaS, where relationships are long-term and success often depends on trust, upselling needs to feel like a natural extension of your customer success efforts.

A customer-centric approach to upselling considers the customer’s needs, timing, and goals. It shows your commitment to their success by offering them solutions that genuinely benefit them.

For instance, rather than pushing a premium feature from the start, it may be more effective to introduce it once a customer’s usage indicates they’d benefit from it.

1. Start with a Deep Understanding of Customer Needs

Conduct Regular Health Checks and Check-ins

An upsell that adds real value requires a deep understanding of the customer’s goals and challenges. Conducting regular health checks and periodic check-ins with customers helps you stay in tune with their current needs. Customer success teams should aim to understand each account’s unique pain points, usage patterns, and growth ambitions, allowing for a more targeted and meaningful upsell approach.

For example, a project management SaaS might notice a client regularly using a specific task automation feature. During a check-in, the success team could discuss how the premium automation features could further streamline their workflows and save them even more time.

Use Data to Anticipate Customer Needs

Customer data can reveal insights into when and where an upsell makes the most sense. Track metrics such as feature usage, login frequency, and product interactions to identify trends that indicate a potential upsell opportunity. If data shows that a customer is frequently reaching the limit of their current plan, it may be the right time to discuss an upgrade.

Actionable Tip: Set up automated alerts for customer success teams when certain usage thresholds are met (e.g., nearing storage capacity or active user limits). This allows you to reach out with an upsell that solves an imminent need.

2. Focus on the Value, Not the Price

Explain the Benefits in Terms of ROI

For B2B customers, upsells are most effective when they’re presented as investments in better outcomes, not just an added expense. When discussing an upsell, focus on how it addresses specific challenges and offers a return on investment (ROI). Explain in concrete terms how the additional feature or plan upgrade can save them time, reduce costs, or help them achieve measurable results.

For example, a SaaS platform providing analytics tools might present an upsell that includes advanced reporting features. Instead of focusing on the monthly cost, the discussion should emphasize how the new reports could give the customer insights to increase their own customer retention or streamline their internal processes.

Share Real-Life Success Stories

Sharing success stories from other customers who upgraded and saw positive results can make a strong case for the upsell. Real-life examples help potential buyers see the value in action and reduce perceived risks. Customer success managers can share stories of clients in similar industries or roles who have benefited from the upsell, using relatable examples to illustrate the value.

Actionable Tip: Build a library of success stories and case studies segmented by product feature and industry. This way, when a relevant upsell opportunity arises, your team can quickly reference stories that resonate with the customer’s specific needs.

3. Use Timing to Your Advantage

Upsell During Milestones, Not Just Renewals

Many companies only attempt upsells during renewals, but this can feel like an afterthought rather than a value-add. Instead, try to identify other strategic times to present an upsell, such as at milestones in the customer’s journey. Milestones like achieving an internal goal, completing onboarding, or a year-end wrap-up call provide natural opportunities to introduce an upsell in a context that aligns with their current successes and goals.

For instance, if a customer has just completed a successful onboarding and integrated your software into their workflows, they may be ready to consider additional features to scale usage. Celebrating their onboarding success with an upsell can reinforce the positive experience they’ve had so far.

Introduce Upsells When Customers Face New Challenges

Upsells work best when they directly address new challenges or requirements. When a customer’s business grows or their team expands, their needs often shift, creating natural opportunities for new solutions. During check-ins, customer success teams should listen carefully for cues about these changes. If a client mentions recent growth or scaling challenges, you can introduce a feature that will help them adapt, making the upsell feel like a solution to a newly emerging problem.

4. Build Trust through Transparency

Offer Trial Periods or “Test Drives”

Letting customers “test drive” premium features reduces the pressure and gives them a low-risk way to experience the value firsthand. Offering a trial period on advanced features or higher-tier plans builds trust by demonstrating that you’re confident in the product’s value. If customers find the feature beneficial, they’re more likely to convert without feeling pushed.

For example, if your SaaS product offers a basic reporting dashboard but has an advanced analytics package as an upsell, consider offering a 30-day trial of the advanced package. This way, customers can explore the value for themselves.

Be Transparent About Costs and Benefits

A transparent approach to upselling avoids hidden fees and vague promises. Clearly explaining what’s included in an upgraded package and its associated cost goes a long way in building trust. Rather than pushing for an immediate decision, provide all the information the customer needs to make an informed choice.

Actionable Tip: Create clear documentation that outlines each pricing tier, feature, and the benefits of each upgrade. Empower your customer success team to answer any pricing questions directly and confidently.

5. Use Upsells as a Way to Deepen Relationships

Frame the Upsell as a Collaborative Success Step

Rather than positioning an upsell as a product pitch, frame it as the next logical step in your customer’s journey. When customer success teams work closely with clients to achieve milestones, they naturally learn where the product can provide more value. Offering an upsell based on that relationship-focused interaction demonstrates that you understand their goals and are committed to their long-term success.

For example, if you know a customer’s goal is to expand into new markets, suggest tools or upgrades within your platform that can support that expansion. This framing shows that you’re invested in helping them grow rather than simply making a sale.

Regularly Revisit and Refine the Customer’s Needs

Customer needs aren’t static. Reaching out periodically to reassess their goals and update their usage preferences reinforces your commitment to their success. Conduct quarterly or biannual reviews to ensure the customer is getting maximum value and address any gaps they might be experiencing. During these reviews, potential upsells can be introduced as solutions that address new needs or goals, making them feel organic rather than sales-driven.

Actionable Tip: Use these review sessions to recap recent wins and challenges. Position any upsell as a way to address current pain points or reach the customer’s latest business objectives.

6. Avoid Overloading Customers with Options

Keep Upsell Choices Simple and Relevant

When it comes to upselling, presenting too many options can overwhelm customers and slow down decision-making. Instead, focus on a single, highly relevant upsell option at a time, based on customer usage patterns and needs. Prioritizing one key upgrade makes it easier for customers to see the immediate benefit without getting bogged down in decision fatigue.

For instance, if a customer is on the “Professional” plan, don’t offer three different upgrade options at once. Suggest the “Enterprise” plan as the next logical step based on their usage. Keep it simple and specific to their current stage of growth.

Avoid Upselling Too Early in the Relationship

Timing is everything. For new customers still in the early stages of using your product, an upsell may feel premature. Let customers experience the core product and reach initial milestones before offering an upgrade. For instance, if a customer is still completing their onboarding process, focus on helping them get value from the base product first.

A customer who’s already seeing value in the current product is far more receptive to upsells than one still learning the basics.

Conclusion: Building Long-Term Value with Strategic Upsells

The art of the upsell in B2B SaaS isn’t about maximizing revenue in a single transaction—it’s about building trust, delivering value, and positioning your product as an ongoing solution to your customers’ evolving needs. Done right, upselling strengthens customer relationships, increases lifetime value, and positions your SaaS as an essential part of their success.

The best upsells focus on customer needs, are introduced at the right time, and are presented with transparency and trust.

When customer success teams approach upselling as a collaborative process, it deepens relationships and creates a win-win situation where both the SaaS provider and the customer see greater value.