Google (Worst) Upsell Masterclass You Wouldn’t Expect

How many times have you heard—especially in young, dynamic environments—that big companies are the ultimate examples to follow? “Learn from the best,” they say. But today, we’re flipping the script. This isn’t about best practices; it’s a lesson on what not to do when building a B2B upsell workflow, inspired by a case study from none other than Google.

What Is an Upsell? A Quick Primer

Upselling is the art of encouraging customers to upgrade or purchase additional features or services. For SaaS B2B companies, upselling is a strategic lever for revenue growth and cost reduction. It typically happens during key moments in the customer journey—when a user is nearing a plan’s limits, exploring new features, or requiring additional support.

In a Product-Led Growth (PLG) model, effective upsell workflows are crucial. They need to be data-driven, timely, and seamless to ensure users stay engaged and satisfied.

Carmelo Squillaci - A visual representation of strategic upselling in the SaaS B2B industry, showcasing innovative approaches to enhance sales.

Google’s Upsell Workflow: A Case Study in Complexity

Let’s set the stage. Imagine you’re a Google user nearing your storage limit. Instead of receiving a clear path to upgrade, you encounter a maze of errors. Here’s where Google’s process falters:

1. The Importance of a Trigger

An effective PLG flow begins with a well-timed, personalized notification:

  • Example: “Hello, [First Name], You’ve consumed 80% of your Google One storage space.”
  • Key Traits: Data-driven, time-sensitive, and user-specific.
Illustration highlighting the significance of upsell triggers in enhancing performance and decision-making processes -  Carmelo Squillaci

2. Errors That Derail the Journey

Friction-Inducing CTAs

Google’s landing pages often contain two conflicting CTAs, creating decision fatigue.

Legacy Pages

Outdated interfaces increase friction and make users question the reliability of the process.

External Redirections

Redirecting users to external spaces disrupts their journey. Research shows that 50% of users abandon the process when redirected.

Inadequate Plan Comparisons

Without transparent pricing or feature comparisons, users feel stuck. A lack of a “Discover More” section leaves them uninformed and frustrated.

Unclear KPIs

Hard-to-measure KPIs can lead teams to incorrect conclusions. For instance, thousands of clicks but zero conversions often indicate a workflow issue, not a lack of interest.

Google One Upsell interface showcasing diverse steps, highlighting the non user-friendly navigation and choices - Carmelo Squillaci

3. Real-World Impact

For a user, these missteps turn an upsell attempt into a nightmare:

  • Four steps into the process, and they still don’t know the upgrade cost.
  • The journey becomes so frustrating that it becomes a question of principle—abandon the workflow or stay out of spite.
  • Keep in mind that By step two, 50% of users have already left. 

Lessons for SaaS B2B Companies and Startups

1. Build Data-Driven, Time-Sensitive Workflows

Notifications should be personalized and triggered by user behavior, such as reaching 80% of a plan’s capacity. Ensure they create urgency without being intrusive.

2. Prioritize User Experience

  • Avoid multiple CTAs.
  • Modernize legacy pages.
  • Keep users within your platform to reduce drop-offs.

3. Make Pricing Clear and Accessible

Add a “Discover More” section and offer transparent plan comparisons to empower decision-making.

4. Measure the Right KPIs

Track meaningful metrics like conversion rates per step, time spent on pages, and user drop-offs to continuously refine workflows.

Conclusion

Even giants like Google can stumble. As your SaaS B2B startup grows, remember that complexity should never come at the expense of user experience. A well-designed upsell workflow not only drives revenue but also builds trust and long-term loyalty. Learn from Google’s missteps: keep it simple, clear, and user-focused.

FAQs About B2B Upsell and PLG

What Is the Difference Between Upsell and Cross-Sell?

  • Upsell: Encourages customers to purchase a higher-tier plan or additional features.
  • Cross-sell: Promotes complementary products or services.

Why Is PLG Important for Upselling?

PLG focuses on the user experience, making it easier to identify and act on moments of need. This approach increases the likelihood of successful upsells by leveraging in-product triggers.

What Are Common Metrics to Track in Upsell Campaigns?

  • Conversion rate per step.
  • Time spent on upsell pages.
  • Drop-off rates.
  • Average revenue per user (ARPU).

How Can Startups Avoid Friction in Upsell Flows?

  • Use clear, concise CTAs.
  • Eliminate unnecessary steps.
  • Provide transparent pricing and feature comparisons.
  • Avoid redirections that interrupt the user journey.

What Tools Can Help Build Effective Upsell Workflows?

  • Customer.io: For personalized notifications.
  • UserPilot: For in-app user journeys.
  • Google Analytics: For tracking and refining workflows.

TL;DR

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Curious if your SaaS strategy is working?

I’m Carmelo Squillaci, Senior Product Marketing Manager with expertise in marketing strategies and go-to-market execution, I help your SaaS business scale effectively and reach its full potential.

Wondering if your company is applying the right strategies discussed in this article? I’m based in Barcelona and available online even for a digital coffee.