Scaling Payment Adoption from 60% to 98% GDV at GoFundMe Pro

I started by architecting the go-to-market foundation in a multi-tab spreadsheet — or my analogy of "dumping the Legos on the floor." This helps me audit the “from → to” states across product value, existing messaging, channel assets, planned innovation, customer lifecycle, highest-value accounts, and points of friction.

I anchored the strategy in segmentation, targeting, and positioning (STP) — segmenting customers by type, lifecycle stage, processor, revenue potential, buying persona, and objection.

I also flexed the messaging by buyer and moment using a Gain, Logic, Fear (GLF) framework I learned in B2C financial services. For example, a gain appeal focused on improved conversion and a better donor experience, logic highlighted industry trends, ROI and performance data, and fear appeals could spotlight the risk of staying on inferior infrastructure, superior uptime, or fraud protection.

The first real decision was structural. I rejected a one-off launch campaign in favor of an always-on adoption engine. I mapped the funnel from awareness through interest, commitment, activation, realization, and expansion. Then paired trigger moments and contextual entry points—a campaign launch, reporting activity—with a relevant message and one clear next step across web, email, in-product prompts, and post-sales plays.

My operating principle was simple: reinforce the last positive behavior and prescribe the next valuable step.

Mapping the funnel helped me diagnose the market and adapt more quickly. It also exposed a key insight from this project: a “stalled activation” cohort of customers who signed the contract but never turned it on. The problem wasn’t awareness or intent; these accounts had already committed. They were stuck between the signature and the switch. That insight moved the work from “promote a payment product” to “remove the specific friction keeping committed customers from going live and realizing value.”

I built targeted interventions for that cohort—lifecycle emails, in-product messages, ROI calculators, and post-sales re-engagement playbooks. I worked with Ops to operationalize the system across teams: adoption dashboard, target-account lists, and a self-serve landing page and opt-in flow. Weekly cross-functional reviews with product, engineering, post-sales, lifecycle, and operations surfaced blockers such as rate objections and evaluation friction; we responded with new solution maps, promotional packages, and product prompts.

Finally, we made a concerted effort to close the loop with value realization—showing customers before-and-after performance, such as mobile conversion—so activation also built trust for the next product launch and adoption decision.

I built and connected everything using our new martech stack: Marketo Engage handled marketing automation and email campaigns, including the landing page and workflows I built for Classy Pay. That kept every CTA and form submission inside the same system, where it could trigger follow-up by the account team instead of leaving leads in a campaign queue. I also built upgrade, expansion, and marketing playbooks for the post-sales and CSM teams using Gainsight CS.

Salesforce Sales Cloud was the operational backbone. It connected the marketing activity to post-sales contracting and upgrade workflows, while our operations team used it to build the unified Classy Pay adoption dashboard. The dashboard gave teams sortable views by account segment, account owner, and adoption stage, so we could prioritize high-value accounts and see where an account was stalled without reconciling separate spreadsheets.

For contextual in-product messaging and lifecycle prompts, we used Pendo. It let us reach customers at relevant moments inside the product rather than relying entirely on email—for example, when a customer was already engaging with reporting or another related workflow.

AI only played a limited role since this took place in 2021, before it was a regular part of the operating model. The most important capability was not any individual tool, but the connection between systems, strategy, and the internal teams across product, marketing, and customers. Today, I would keep that unified workflow and add AI to accelerate and scale customer insights, message testing, and campaign analysis—but not at the expense of a clear strategy and compounding GTM engine.

We exceeded the 85% fiscal-year target, moving Classy Pay from 60% to 88% of platform gross donation volume (GDV) by the year-end giving season. Within 12 months, adoption exceed 98% of total GDV—making Classy Pay the payment solution for every customer, minus a few edge cases, and setting the foundation on which all future innovation would be built. That represented more than $1M ARR from contract upgrades and millions in annual transaction fees.

The work also changed how the company managed adoption. “Stalled activation” became a named stage in the funnel, and “customer value realization” became a core principle in how I approach product marketing.

Most importantly, the engine became a reusable model that helped fuel the growth and success of the many product launches to come. This was a fun project and the result was a company-wide effort, so the internal alignment and cross-functional operating cadence we established were keys to success. Our jobs as marketers is to own the diagnosis, strategy, sequencing, and cross-functional alignment needed to turn a hard migration into near-total adoption.