• Case Study

Boosting upsell conversion

In late 2021, Zendesk’s expansion rate had flattened year over year. I led a cross-functional design sprint with Product, Engineering, and Design that resulted in Customer-Initiated Boosting (CIB), a self-service upsell trial experience that allowed customers to try add-ons and higher-tier plans before purchasing.

Boosting launched in August 2022 and achieved a 28% conversion rate and $205K in net ARR within its first few months. To scale the program, I led the creation of standardized templates, cutting development time in half and enabling more consistent, customer-first upsell and cross-sell opportunities.

Company

Zendesk

Team

Growth and Monetization

My Role

Design Management, Strategy, Planning

Dates

2021-2025

How Boosting was built and scaled

Identifying the problem & running the Design Sprint (late 2021 – early 2022)

Zendesk’s expansion rate was stagnant, and I was tasked with identifying ways to increase revenue through better customer expansion strategies. In December 2021, I led a design sprint with product, engineering, and design, exploring ways to enhance self-service purchasing experiences.

The birth of Boosting (Q1 - Q2 2022)

One of the key ideas was Customer-Initiated Boosting (CIB)—a self-service trial mechanism allowing customers to test add-ons or higher-tier plans free for 30 days. However, as a design-initiated project in a product-led organization, buy-in was a challenge.

To secure stakeholder commitment, I worked with a senior product designer to quickly prototype Boosting. This visual proof-of-concept persuaded the Director of Product, who assigned a Product Manager to the initiative. After a quick opportunity-sizing exercise from Product, we found Boosting worthy of landing on the Q2 2022 roadmap. Engineering made a full commitment to it, and allocated resources for development.

Below: the rough state of Boosting after the Design Sprint.

 

Below: initial Benefits and Onboarding pages. This placement turned out to be incorrect – the Support product is not where customers are when in a Boosting “mindset” (from UXR insights). Admin Center was a better fit.

MVP launch & initial success (Q3 - Q4 2022)

After a few design reviews and a round of UX Research, the designs were handed to Engineering.

Boosting launched in August 2022, with early success:

  • 28% boost-to-purchase conversion rate.
  • $205K Net ARR won in 2022.

Below: the Boosting MVP experience. This is what we launched initially. Still rough around the edges, design-wise, but it proved its value.

 

Zooming in: the initial entry point.

 

Zooming in: the initial Benefits page.

Taking it up a notch (Q1 2023)

Despite the success, I pushed for design improvements ahead of expansion. I secured the Product and Eng resources for these iterations ahead of the MVP launch. I aligned with my Directors that we needed to get the experience right before leveraging it for other products. If not, we would carry gaps and friction around, and it would be much harder to iterate on later.

We launched Boosting 1.1 in early 2023, making sure we had:

  • More optimized entry points, identifying better customer journey touchpoints and value-driven content.
  • Refined Benefits pages with clearer messaging and value proposition.
  • Stronger post-boost purchase reminders.

This push contributed to a “sweet” increase in key metrics:

  • Higher Boost Adoption. The highest volume of boosts was recorded in Q1 2023, showing improved visibility and entry points.
  • Better Post-Boost Follow-Through. Improved reminders helped drive higher purchase completion rates.

Below: improved value-driven entry point. Same location, just more effective.


Below: example of a new, in-context entry point.

 

Below: another example of a new, in-context entry point.

 

Below: improved Benefits page. The result of my push for higher quality – improved UI and Content Design.

Expanding Boosting (Q2 2023 on)

Recognizing the potential of Boosting, I led its expansion beyond core plans, bringing it to:

  • AI add-ons, increasing cross-sell opportunities.
  • More Zendesk products, aligning Boosting with the company’s broader expansion strategy. 

Below: Boosting applied to our AI add-on. Overview of the Figma file as it’s hard to reproduce it with a test account. See the higher quality design compared to the MVP.

Scaling Boosting with templates for faster execution (Q3 2023 - Q1 2024)

A major challenge emerged: Boosting projects took too long—each new iteration required 2-3 months of development, slowing business impact.

Why “too long”? Because we could not justify taking a quarter to develop Boosting for one add-on. At that pace, we’d need years to cover our catalog.

My Product and Eng Directors knee-jerk reaction was to add more resources. I disagreed. Yes, Boosting was a key initiative, but we couldn’t halt our massive roadmap just for one Expansion play. That’s when I started thinking of the lessons from “The Goal” by Eliyahu M. Goldratt. What’s the bottleneck? How do we exploit it? Templates.

To solve this, I first pitched, then collaborated with the Director of Product and Director of Engineering to create the “Boosting templates”:

  • Figma-based Boosting Kits for designers and content teams, reducing design time from one month to two weeks.
  • Standardized engineering frameworks, cutting dev time from six weeks to four weeks.
  • Lead Product Designer assigned as DRI, maintaining template relevance based on the latest experimentation data.

The result was cutting product development time from 2-3 months to ~1.5 months.

 

How the Boosting Kit works. It makes it really easy for Designers, PMs and Engineers to understand how boosting works. In a matter of days, teams can spin up their Boosting product!

Final impact & key learnings

By 2024, Boosting had evolved from an experimental initiative to a scalable, repeatable design and engineering system, enabling:

  • Faster go-to-market for new boosting opportunities
  • Increased self-service expansion and cross-sell success
  • A more customer-first way to introduce product upgrades

Through strategic design leadership, iteration, and systematization, Boosting became a cornerstone of Zendesk’s monetization strategy, delivering both customer value and revenue growth.