Key Strategies for Upselling and Cross-Selling[HD1] [נה2]  To Drive Expansion Revenue

Introduction 

It's no secret that profitable growth is a primary goal of most companies. Expanding earnings from existing from existing customers is at least as important as acquiring new ones. At the core of that goal are two techniques: upselling and cross-selling.[HD3] [נה4] 

Discover how upselling and cross-selling drive profitable growth. Learn who to sell to, how to package and price to drive upsell and cross-sell, and why leading enterprises are moving to Portfolio Monetization to scale revenue across their all product lines.[HD5] [RJ6] 

What Is the Difference Between Upsell and Cross-Sell in Software

What Is Cross-Selling?

Cross-selling is a business strategy where you sell related or complementary software products to an existing customer alongside their current purchase or subscription. It’s all about breadth. 

To be successful with cross-selling, your company needs two complementary strategies. First, you need to offer a variety of products, modals, or services that are adjacent to your existing products. Second, you need to be able to package your existing products into bundles that address different use cases. Instead of selling one product that does everything, you create distinct product bundles that each have a core purpose and value[HD7] [נה8] . This second strategy allows you to make more money from the products you already have. No product development dollars required. For more details about implementing this strategy, read below about how to design these bundles. 

Examples of Cross-Selling Strategies:

• Selling analytics dashboards or reporting tools to customers who already rely on your operational software.

• Introducing security, compliance, or backup modules to customers managing sensitive data.

• Offering training packages or professional services to increase time-to-value.

What Is Upselling?

Upselling is a business strategy that focuses on increasing the average order value by encouraging customers to purchase higher-tier plans, unlock additional features, increase limits, or scale up user access. It’s about deepening their engagement with a solution they already trust. 

To be successful at product upselling, companies need to identify the value metric that intuitively incentivizes customers to expand—making the upsell a natural next step. That means choosing a value metric that aligns with how customers actually experience your product’s worth. For example, charging per user (seat-based) only works if the product’s value increases with each additional user. But if the value is tied to data processed, files stored, or number of service hours provided, your pricing needs to reflect that reality.

Examples of Upselling Strategies:[RJ9] 

• A growing company increasing user seats after outgrowing initial purchase 

• A usage-based customer exceeding thresholds and transitioning to a higher-volume package 

• A customer on a “Standard” plan upgrading to “Enterprise” to access role-based  controls or premium support,

Who Should You Upsell and Cross Sell To?

Pinpoint Expansion-Ready Accounts with Product Usage Data

The key to deciding who to target for upselling and cross selling is understanding how customers use your products. Product usage insights include being able to track which features are being used and how often and provide the ability to break down that information into patterns. These patterns, combined with other signals[RJ10] , can help you identify customers with the highest buying intent. 

For smaller companies or vendors with a limited install base, spotting opportunities can be relatively straightforward. You might notice a customer using a feature more often, reaching a usage cap, or asking about new capabilities. Sometimes these signals are picked up organically by customer success or account management.

But that doesn’t scale.[HD11] [KD12] 

Larger companies with more complex product portfolios face a different challenge: separating the right signals from the noise[RJ13] . In enterprise sales, where each account may include dozens—or even hundreds—of users across multiple departments, it becomes difficult to understand what’s happening within the account.

Worse still, many sales and customer success teams are operating without clear, account-level usage visibility. They might have access to CRM data and a record of renewals, but little insight into how the product is being used across teams or what features are being adopted.[HD14] [נה15] 

These Product Usage Data Points Signal Upsell and Cross-Sell Opportunities

Clear, data-driven indicators help your sales, success, and product teams engage at the right moment, with the right offer.

Here are some of the most reliable signals to watch for:

• Usage Limits or License Overage Reached

  • When customers regularly hit seat, usage, or feature limits, you know that i they’re ready to move to a higher tier or volume package.

• Full Entitlement Utilization 

  • A customer activating everything that was in their entitlement prior to renewal time signals strong value recognition and the potential to upgrade them. [HD16] [KD17] 

• Low Adoption of Related Products or Product Lines 

  • Your portfolio may include more products that could be valuable to a specific customer. You can uncover whitespace by understanding the cross portfolio or cross product line adoption. [HD18] [KD19] 

• Early Signs of Customer Disengagement 

  • While not a cross-sell trigger, if a customer is not deploying the products they purchased or not activating specific features, you can step in with a well-timed re-engagement plan.[HD20] [נה21] [HD22] [נה23] 

From Signals to Sales: Using Packaging and Value Metrics to Maximize Expansion Revenue

Designing Product Bundles That Make Cross-Selling a Natural Next Step

Bundling features, capabilities, and add-ons into sellable units creates structure and indicates you are thinking in a customer-centric way. Packaging does two things. It makes the product easy to understand. And it shows customers that you understand them. For example, offering a plan for teams of 0- 10, tells startups you’ve thought about their needs. An enterprise plan tells larger buyers you’re ready for scale. When you get packaging right, you open the door to cross-sell because customers can clearly see how purchasing a different part of your portfolio will help them further their goals.

Bundling related capabilities—like analytics with security, or storage with product management—helps customers understand the value of various product capabilities. From there, it’s easier to show them what else they might need[נה24] , making cross-sell feel organic, not forced when customers see the logic. They recognize the added value that makes the cross sell natural. [HD25] [DK26] 

Finding the Right Value Metric to Make Upselling Intuitive and Frictionless

Compared to cross selling, which centers around complementary products and features, upselling is often about usage and the value metrics that track it. The value metric is what your pricing is built around—number of users, length of documents, quantity of API calls, credits, volume of data. Tracking and pricing that value metric correctly can unlock upselling opportunities, making it intuitive for your user base[HD27] [נה28] . But first, you have to find a value metric that feels so logical customers don’t think twice about upgrading. 

But get it wrong and upsell and expansion becomes harder. For example, if you sell a security platform that ingests data and then generates dashboards to provide anomaly detection alerts, and your sales team tries to sell more seats, they might struggle to expand. In this example, the numbers of users aren’t the best value metric to tie the expansion to. The core value is tied to the data ingested.  So, sales should offer higher data ingestion tiers or bundles that unlock more storage, processing capacity, and alerting coverage. This way they align the upsell with the customer’s growth in monitored data rather than their headcount. By establishing your offer around the metric, that matches how customers see value, expansion is easy. 

In this example, Outseta is monetizing the number of contacts each account can store in the platform. The number of contacts was the metric they chose to monetize, as opposed to number of seats, users, or volume of usage. For this product, the value comes from how many contacts you have in the system. Creating an offer based on that metric makes for an easy upsell. 

Hybrid Pricing Models Create Even More Upsell and Cross-Sell Paths

Some products deliver value in more than one way. In those cases, a single value metric might not be enough. That’s where hybrid pricing models come in.

Hybrid models combine different ways of charging. For example:

• Charge a flat fee for access (e.g., per user),

• Then add usage-based pricing (e.g., per scan, per GB),

• Or let customers buy credits they can spend across features or teams.

This gives you more flexibility. It also gives customers more choice. Light users can start small. Power users can scale without friction. And you create multiple expansion triggers—not just one.[HD29] [DK30] 

Enterprise Sales Requires Refined Upsell and Cross-Sell Strategies 

In smaller or single-product environments, upselling and cross-selling are effective strategies for driving expansion. They allow vendors to deepen customer adoption and introduce complementary capabilities, often with minimal coordination or infrastructure.

In large enterprises, however, these approaches face significant limitations. Customers interact with multiple products, teams, and contracts—often across global regions and business units. Expansion becomes more difficult to execute and even harder to manage consistently.

Portfolio Monetization Provides a Scalable Framework for Enterprise Growth

Portfolio Monetization addresses these challenges by introducing a strategic, system-level approach to enterprise-scale expansion. At its core, Portfolio Monetization is packaging, distributing, and tracking multiple product lines with a cohesive commercial strategy—designed specifically for complex, multi-departmental enterprise environments. It involves balancing flexible offerings that meet broad organizational needs with streamlined visibility through centralized systems like CRMs or EMS platforms. 

By designing packages with complex enterprises in mind, companies can move beyond isolated product growth and toward unified monetization across the entire portfolio. Instead of managing upsell and cross-sell as individual motions within separate product lines, Portfolio Monetization establishes a commercial framework that spans:

• Multiple SKUs and packaging tiers, [RJ31] 

• Distinct but related product families,

• Cross-functional enterprise use cases,

• Global customer segments with varied buying needs.

When these structural issues are addressed, upsell and cross-sell motions become easier to execute—no matter how complex the customer or product portfolio. Portfolio Monetization turns ad-hoc growth into a repeatable, scalable strategy that drives consistent expansion across the full enterprise customer footprint.[HD32] [DK33] [HD34] [נה35] [RJ36] 

When enterprises sell into other enterprises, this is portfolio monetization is often implemented through Enterprise License agreements. ELA’s provide a fixed-budget, flexible-consumption model that simplifies procurement and encourages broad product uptake—particularly when buyers have the authority to drive cross-departmental adoption. However, a well-structured Portfolio Monetization strategy goes beyond Enterprise License Agreements, combining smart pricing, aligned go-to-market efforts, and smooth execution to drive growth and value. It also enables smaller bundles that, while not ELA-sized, effectively serve targeted market segments.

Conclusion: Driving Profitable Growth Through Smarter Upselling and Cross-Selling

Expansion revenue is the most efficient path to growth for today’s enterprise software leaders. And it starts with smarter, data-driven upselling and cross-selling.

Ready to unlock more expansion revenue across your software portfolio? [Talk to our team] or [Explore Thales Sentinel’s entitlement and monetization solutions].

Thales Sentinel Upsell and Cross-sell Support FAQs [HD37] [RJ38] 

1. What’s the difference between upsell and cross-sell in software?

   Upsell is encouraging customers to upgrade to a higher-tier product or add premium features for greater functionality. Cross-sell is promoting complementary products that add value to their existing purchase. Both upselling and cross-selling strategies drive expansion revenue, but they each require different packaging, pricing, and entitlement approaches.

2. How can product usage data support expansion revenue?

   Product usage data helps identify customers ready to upgrade (upsell) or adopt adjacent products (cross-sell), driving targeted, data-backed offers that increase revenue per account.

3. How does Thales Sentinel help sales and customer success teams identify upsell and cross-sell opportunities? 

   Sentinel Pulse integrates product engagement insights directly into your CRM like Salesforce or Dynamics, showing: 

• Account-level usage summaries

• Entitlement consumption data

• License activation trends

These insights highlight customers who are highly engaged (ideal for upsell/cross-sell) or under-utilizing licenses (potential churn risk). Sales teams can prioritize accounts, tailor outreach, and drive expansion confidently without leaving their CRM.

4. How does Thales Sentinel support modular product packaging for upsell and cross-sell?

    Sentinel’s product catalogue allows you to bundle products, features, and components into unique packages that align with customer needs while creating clear upgrade paths and cross-sell opportunities.[RJ39] 

5. Can I test and iterate new product bundles or packages in-market using Sentinel?

   Because the Sentinel platform allows you to create packages without code changes, Sentinel allows you package and price offerings in ways that align with customer needs while creating clear upgrade paths and cross-sell opportunities.

6. How does Thales Sentinel ensure customers clearly see what’s included in each package?

    

   Sentinel manages entitlements at a granular level, ensuring customers only access what they’re licensed to use. Through integration with your product UI or through Sentinel’s customer portal, customers can clearly see available licensees, what’s been deployed, and what’s included in their packages. 

    

7. How does Thales Sentinel help define[RJ40]  and operationalize the right value metric for my product?

    

   Sentinel supports multiple value metrics, including usage-based, user-based, device-based, or hybrid models. You can align pricing to customer-perceived value, then operationalize it seamlessly through entitlements, license enforcement, and integrated usage tracking for billing and insights.

    

8. Can I [RJ41] implement hybrid pricing models with Thales Sentinel?

   Yes, Thales Sentinel supports hybrid pricing models. You can combine subscriptions, usage-based charges, user-based fees, and feature-based tiers into flexible pricing structures that align with customer value and maximize revenue. Sentinel EMS manages entitlement configurations for these models, while Sentinel LDK enforces them[RJ42] 

    

9. How does Thales Sentinel support upsell and cross-sell across complex enterprise accounts?

   Thales Sentinel supports upsell and cross-sell in complex enterprise accounts by providing multi-level visibility into license adoption across divisions and business units, highlights where upgrades or additional products will drive the most value and delivers real-time alerts in your CRM.