For SaaS companies looking to scale, upselling is one of the most effective—and often underutilized—revenue levers. Instead of pouring resources solely into acquiring new customers, smart SaaS businesses focus on increasing revenue from existing customers by guiding them to higher tiers, unlocking premium features, and expanding their usage.
This guide explores the ins and outs of SaaS upselling, from the strategies that work best to the tools and timing that maximize results. Whether you’re a startup with a freemium model or an enterprise SaaS subscription, upselling and cross selling can drive lasting growth by enhancing customer satisfaction and increasing customer lifetime value.
TL;DR
- SaaS upselling helps increase revenue from existing customers by guiding them to higher-tier plans, unlocking premium features, or expanding usage.
- Well-timed upselling and cross selling efforts—triggered by user behavior, milestones, or usage patterns—can significantly boost customer lifetime value and reduce customer acquisition costs.
- Top upsell strategies include offering advanced features, expanding seat count, and introducing payment processing capabilities. Delivering upgrade prompts through in-app messaging, email automation, and customer success outreach makes the upsell process feel personalized and value-driven.
Join the Payments-Led Growth Movement
Sign up to keep up-to-date with the latest trends in payments, vertical SaaS, and technology from industry experts.
What is SaaS Upselling?
SaaS upselling is the practice of encouraging customers to upgrade from their current plan to a higher-tier plan or add premium features that deliver more value. It’s a sales technique focused on delivering tailored enhancements based on the customer’s current usage, needs, or goals.
For example, a team on a basic plan might be prompted to unlock advanced features such as automated workflows, premium analytics, or dedicated support. These upsell opportunities not only generate more money for your business but also improve the customer’s experience by solving pain points or scaling with their growth.
In contrast to cross selling, which promotes complementary products or add-ons, upselling focuses on enhancing the customer’s initial purchase.
Common Upsell Strategies in SaaS
There are several upselling strategies SaaS companies can use, depending on the product structure and customer journey. Consider the following.
Entice them with feature upgrades
One of the most effective ways to drive growth from your existing customer base is by offering targeted feature upgrades. These are premium features that solve more complex problems, automate tedious tasks, or unlock new capabilities for growing teams.
Let’s say your customer has been using your billing software to send out invoices. They’re seeing great engagement, and they’re ready for more. That’s an ideal moment to upsell payment processing, enabling them to accept credit cards, ACH transfers, or digital wallets directly through their invoices.
With integrated payments, they can speed up cash flow, reduce manual reconciliation, and offer a smoother experience to their clients—all within the same platform.
The key is to make the upgrade feel like a natural next step, not a hard sell. Use in-app messaging to surface new features when users hit limits or show interest in functionality that lives behind a paywall. For example, if a user tries to access a locked feature, show them what’s possible with a premium version—include real results or testimonials to reinforce the value.
Remember: your goal is to enhance the customer’s experience, not just add more features. When feature upgrades align with actual needs and usage patterns, they’re seen as valuable investments—not expenses.
See if they’d like to expand their usage tiers
As your customers grow, their needs do too—and that’s where usage-tier upsells shine. These strategies center on expanding access to your product based on consumption metrics like volume, bandwidth, number of contacts, API calls, or storage limits.
Let’s say you offer a CRM that allows users to store up to 5,000 contacts on the base plan. Once a customer gets close to that limit, you can surface an upgrade prompt that congratulates them on their growth and offers a seamless path to the next tier. This kind of messaging reframes the upsell as a celebration of success—not a constraint.
A well-timed upsell feels helpful, not intrusive. You’re saying, “You’re doing great. Here’s how we can support you as you scale.”
To do this well, you need visibility into usage patterns and the ability to trigger personalized messages or emails based on thresholds. And don’t underestimate the power of your pricing page—make sure it clearly outlines what’s included in each tier so customers can see the value of upgrading.
Offer seat expansion
If your product serves teams or organizations, seat expansion can be a powerful upselling strategy. As your customer’s team grows, so does the opportunity to increase the number of paid users on the account.
Start by making it easy to add users with just a few clicks. Then, use product usage data to trigger smart prompts when team members are collaborating more, projects are increasing, or admin users attempt to invite new people. You can even offer a short trial for additional seats, allowing teams to test the workflow benefits before committing.
For SaaS companies with sales-assisted models, customer success or account managers can proactively reach out when growth is detected. A quick conversation around operational pain points can turn into an upsell offer for additional seats and premium features like role-based permissions or team reporting.
Offer premium support or onboarding
Sometimes, the biggest value-add isn’t a product feature, but hands-on support that helps customers get results faster. That’s where premium support or onboarding packages come in.
Many SaaS businesses offer this as a paid add-on or bundled into higher-tier plans. Whether it’s priority chat access, a dedicated onboarding specialist, or a customized implementation plan, these services help reduce time-to-value and create a smoother experience for customers who need extra help.
This strategy is especially effective for new customers with complex setups or current customers who are upgrading to a more advanced product suite. Offering a premium onboarding package removes friction and gives them confidence they’ll get a high ROI.
From a revenue perspective, this type of upsell has high margins and often leads to stronger customer relationships. It’s a win-win: your team delivers more value, and your customer gets more confidence—and results—from day one.
When to Upsell in SaaS: Identifying the Right Moments
Timing is everything in SaaS upselling. Push too early, and the offer feels aggressive. Wait too long, and you miss the window of opportunity. Here are some moments that lend themselves to upselling opportunities.
- Onboarding – The onboarding phase is all about momentum. If a new user is moving quickly through setup, exploring advanced workflows, or showing signs of long-term fit, it’s the perfect time to introduce light-touch upgrade prompts.
- Feature discovery – When a user actively explores a premium feature, they’re signaling intent. Maybe they click on a locked dashboard or try to enable advanced integrations. Use that moment to show them how unlocking that feature can solve a specific pain point or boost performance.
- Milestone achievements – Celebrate your customer’s progress by showing them what comes next. Hit their first 1,000 orders? Launched a new product line? Those are signals they’re growing, and thus a great time to introduce premium features that support their next phase. Make the upsell feel like a natural part of the journey, not a detour.
- Usage limits – Approaching or exceeding usage limits is a prime opportunity to upsell. Whether it’s data storage, transactions, or users, frame the conversation around momentum. Say something along the lines of: “You’re growing fast—let’s keep things running smoothly.” Help them see the upgrade as removing roadblocks, not adding costs.
- Renewal periods: When renewal time rolls around, customers are already reflecting on the value they’ve received. That makes it an ideal time to offer bundled upgrades or custom plans that align with their growth. If you’ve delivered strong outcomes, an upsell at renewal can feel like a logical next step.
The bottom line? Upselling efforts should always be tied to actual user behavior or customer success milestones.
Channels for Delivering Upsell Offers
We’ve talked about why and how to upsell; now, let’s look at the channels and methods you can use to deliver your messaging and prompts around upselling.
In-app messaging and tools – Use contextual messages triggered by usage patterns or feature exploration. Let’s say a user clicks into your billing features and tries to enable built-in payment processing in this instance, a subtle tooltip or modal can prompt them to upgrade to a plan that comes with merchant services.
Email automation – Send upsell campaigns based on customer segments or engagement levels. For example, if a user consistently maxes out their monthly invoice volume, an automated email can highlight a higher-tier plan with expanded capacity and premium features that support their continued growth.
Customer success outreach – Have your customer success team personalize upgrade prompts during QBRs or milestone check-ins. In doing so, your CSMs can tie the upsell offer to real business outcomes—like improved efficiency, better reporting, or access to premium support—making the recommendation more relevant and impactful.
Checkout and renewal flows – Surface upgrade options when customers are already primed to buy. For instance, when a user is renewing their plan or adding a new feature, you can present a bundled premium plan that includes additional features at a discounted rate, making it easy for them to say yes.
Personalized dashboards or pricing pages – Show a tailored upsell offer based on current usage and goals. That way, customers can clearly see the benefits of upgrading in the context of their own growth, usage data, and business objectives—without having to hunt for information.
Measuring the Success of Your Upselling Strategy
Tracking the right metrics ensures your upselling strategies are working. Here are some of the KPIs to keep in mind.
- Expansion MRR (monthly recurring revenue) – How much revenue comes from upsells.
- ARPU (average revenue per user) – A higher ARPU indicates effective upselling and cross selling.
- LTV:CAC ratio – As LTV increases through upselling, your profitability grows.
- Upgrade conversion rate – The percentage of users who move to a premium version.
- Churn vs retention rate – Successful upselling should correlate with better customer retention.
A Deeper Look at Upselling Payments in SaaS
So far, we’ve talked about SaaS upselling in general. In this section, we’ll be discussing upselling in the context of SaaS payment processing. With financial services increasingly embedded into software platforms, more and more SaaS companies are opting to offer merchant services within their platform.
If you’re one of them, here are some tips that can help you upsell payments to your users.
Talk up your payments and billing capabilities on your website
Users won’t sign up for your payment offerings if they don’t know they exist in the first place. That’s why you need to ensure you’ve set up marketing and advertising assets that can inform your current and existing software users about your payment services.
Not only will this educate them about what you have to offer, but it will also make it easier for your team to upsell payments. Having the right assets gives them collateral to share with users and move them towards the path to purchase.
One example of this could be a time tracking and expense software. In addition to mentioning payments on a homepage, there should also be a section on your website dedicated to the payment processing product and it’s branded name.
Your dedicated payments product landing page should include:
- How it works
- Key benefits to users
- Social proof from other users
Train and encourage your sales team to upsell payments
Your sales team will likely be doing a lot of the legwork to get merchants sold on payments. As such, you need to make sure they have the support and resources they need to succeed. Consider the following tips.
Give your team some talking points
Educate your sales staff on the features and benefits of payments, and provide them with talking points to bring up when interfacing with software users to effectively upsell payments.
ProfitSolv, a company that provides billing, payments, and software solutions for professional services, does this well. Jason Goldfinger, the company’s VP of sales, says that ProfitSolv’s salespeople are trained to create value and get to know each user’s process.
“You build value by asking questions and digging into their current processes,” he says.
Examples of those questions are:
- “Tell me how you guys get paid today” and
- “OK, walk me through the process of how that works.”
From there, the salesperson would help the user see the inefficiencies with their payment systems, which then paves the way for a productive conversation.
For example, if a company is manually entering payment information into its system through an unintegrated processor, ProfitSolv’s team could direct the conversation to its payment initiatives.
That could look something like this:
Salesperson: How many payments do you do per month?
User: Probably around 50
Salesperson: Ok, you’re doing this manual process 50 times per month? (said with a concerned/surprised tone).
This, says Jason, sets the stage for the sales rep to show the value of integrated payments—ultimately helping to increase conversions. Make sure your team knows your competitors
It may also help to teach them about the competitive landscape so they know how your solution measures up against similar providers. This allows them to improve their sales pitch. Competitor battle cards with side-by-side comparisons would be a good tool here.
Incentivize sales
Finally, try to come up with incentives or programs that would further encourage your staff to sell or upsell payments. Reward your best salespeople and recognize the individuals for the deals they’ve closed.
It’s also beneficial to make your sales targets more visible. Having a dashboard indicating how much has been sold and how close the team is to their monthly targets may keep payments top of mind so your sales staff can actively sell and upsell payments services.
Be targeted with your upsells
If you’re looking to upsell payments to your existing users, strive to be more targeted with your efforts. Go through your SaaS payment metrics and userbase to identify accounts that would benefit most from your payment offerings. These could be customers that are using certain features, businesses of a certain size, or those that deal with high credit card volumes.
Whatever the case, figure out your “best fit” users for payments and prioritize them in your sales efforts. For best results and to upsell payments, tailor your pitch to each user. Have your sales team utilize their history and data so they can customize their customer interactions.
Let’s say you’ve noticed businesses that deal with more than $10,000 in credit card transactions would be a great fit for your payment services. You can use that info to generate a list of users to contact, and then personalize the pitch based on their account activity.
You could say something along the lines of:
“We’ve noticed that your invoiced amounts have hit $10,000 last month. Congratulations on your growth! Given your history, we think you’d be a great fit for our payment services. Here’s why…”
Starting a conversation that’s centered around the users’ needs and activities will make your spiel much more relevant, ultimately improving the chances of conversion.
Bring up payments at the right time and place
When it comes to sales, timing and location matter a great deal. When and where you bring up the payments conversation can make or break your sales. This is why it’s important to pay attention to your typical user journey and identify the points at which to encourage them to use payments.
Let’s suppose you’re selling a client management solution that allows users to keep track of their client engagements and projects. Your software comes with billing and payments capabilities and you’d like to get more of your customers using those features.
With that in mind, you should introduce payments when it makes the most sense for your users. This could be when they already added clients and projects to the software and are ready to bill them.
In this situation, you could prompt people to use your billing and payments services when they’re about to conclude a project.
Consider displaying a software prompt or message that says something like:
“You’ve just marked this project as complete. Have you tried our billing features? XYZ Software makes it easy for you to manage your clients and get paid all in one place.”
By using this approach, your payment features will come up at just the right time, thus piquing user interest. It’s worth emphasizing the fact that using digital or integrated payments would help your users get paid faster. Highlighting these things will not only improve the likelihood that they’ll explore your payment options, it’ll open up more opportunities for you to re-invest in your business.
Showcase your success stories
Do you have existing users that are benefiting from your payment services? Make it a point to spotlight their stories. Produce case studies that outline the problems you’ve helped them solve and the results they’ve seen from using your payment services.
Once you have those case studies, put them up on your website and get your sales team to share them with prospects. Customer success stories are yet another excellent resource that your staff can leverage to market and sell your payment offerings.
Remember that social proof goes a long way. When potential users see businesses like them using your services, they’re more likely to sign up—or at least have a conversation with your team.
Offer promotions to users who get on board
Sometimes, you may need to sweeten the deal to get users on board your payment offerings. If it makes sense for your business, offer a discount on your software subscriptions if users process payments through your platform.
Let’s take a look at what an example of this could look like for a chiropractic software. Offering a $200 credit, for instance, to the user’s account when they sign up for payment processing on your platform is a strong promotional campaign to increase merchants.
To promote this campaign, you could launch an email sequence that:
- Highlights the promotion
- Communicats the benefits of integrated payments
- Promotes a sense of urgency by giving people a deadline for signing up
Consider doing something similar in your business. Just remember to analyze how your payments revenue translates to MRR or ARR. This will help you determine what sort of discount to offer.
Pro tip: A quality processing partner will assist the ISV in this analysis.
Need more help upselling payments to your software users?
If you’re struggling to upsell payments (even with the tips above), reach out to your SaaS payment processing provider. The right partner can help you fine-tune your payment sales efforts to ensure that your team can effectively sell and upsell your offerings.
At Stax Connect, we strive to have a mutually beneficial relationship with all our SaaS partners. We work closely with each partner and empower them to develop powerful strategies for increasing payment adoption.
Get in touch with us to learn how we help SaaS companies and ISVs with their payment monetization efforts.
FAQs about SaaS Payments
Q: What is the importance of payment monetization in SaaS companies?
Payment monetization escalates the use of software and allows users to derive more value from the product, which in return lowers churn. Besides, it opens a new revenue stream, thus strengthening the company’s bottom line.
Q: How can I increase payments-related activity and revenue on my platform?
It’s crucial to convince users (merchants) to process payments through your platform; you can achieve this by upselling your payment services.
Q: What are some effective tips to upsell payment services to users?
Some key strategies include promoting your payments and billing capabilities on your website, training your sales team to upsell payments, targeting your upselling efforts, introducing payments at an appropriate time, showcasing your success stories, and offering promotions to users who sign up.
Q: Why is it essential to promote payments and billing capabilities on my website?
Users need to be aware of your payment offerings in order to sign up. Marketing and advertising assets on your webpage will help educate your current and prospective users about your payment services, making it easier to upsell these services.
Q: How can I train my sales team to upsell payments effectively?
Equip your sales team with talking points on the features and benefits of payments. Also, familiarizing them with the competitive landscape and incentivizing their sales efforts will enhance their ability to sell or upsell payments.
Q: Why is targeting upsells important?
Studying your SaaS payment metrics and user base to identify accounts that could benefit from your payment offerings, then tailoring your pitch to those users, will make your pitch more relevant and increase the chances of conversion.
Q: How can I bring up the topic of payments at the right time and place?
You should consider the typical user’s journey and identify points where encouraging them to use payments makes the most sense. This could greatly impact your sales results.
Q: What is the significance of showcasing success stories?
Showcasing success stories functions as social proof. When potential users see businesses like them benefitting from your services, they’re more likely to sign up or at least have a conversation with your team.
Q: What kind of promotions can I offer to encourage users to sign up for my payment services?
You could offer discounts on your software subscriptions if users process payments through your platform. However, it’s necessary to analyze how your payment revenue translates to MRR or ARR before deciding what sort of discount to offer.
Q: What can I do if I’m struggling to upsell payments to my software users?
If you’re finding it challenging to upsell payments, you can reach out to your payment processing provider for support. The right partner can help you refine your payment sales strategies to ensure that your team can effectively sell and upsell your offerings.
