Episode 62: Payments: a RevOps Problem in Disguise

Welcome back to the RevOpsAF podcast! In this episode, co-host Matthew Volm, CEO and Founder of RevOps Co-op, sits down with Vince Chiofolo, SVP of Revenue Operations at Dash Solutions. Vince brings decades of experience bridging sales, marketing, and operations into a single GTM system. Today, he shares why payments—long treated as a finance or back-office issue—are actually a RevOps problem hiding in plain sight.

While churn is typically attributed to product gaps, bad onboarding, or poor service, Vince points out that nearly 50% of churn in subscription-based businesses is driven by avoidable payment failures—things like expired credit cards, clunky portals, or rejected transactions . For operators laser-focused on NRR and retention, that’s not a “cost of doing business”—that’s an urgent opportunity.

The Hidden Churn Driver: Payment Failures

We all know the classic churn culprits: pricing misalignment, feature gaps, poor CS handoffs. But according to data shared by Vince, one out of every two churned customers may have left simply because their payment didn’t go through.

That’s staggering. Consider this:

• A customer can love your product, engage weekly, and even expand usage—but if their credit card expires and your systems don’t resolve it seamlessly, they’re gone.
• On the outbound side, slow refunds or botched payouts create reputational damage and erode trust just as quickly.

Vince calls this the “fifth P” of GTM—joining product, price, promotion, and place. Payment is part of the buyer experience, and when it fails, every other effort collapses.

“If the payment fails, you can have everything else right—but you still create a really bad experience.” – Vince Chiofolo

Why Payments Get Overlooked

So why aren’t more RevOps teams paying attention? Vince argues it’s because payments have historically lived inside finance, not sales or marketing. Finance teams solve for reconciliation and compliance—but they don’t always consider payments through the lens of customer experience.

Yet modern GTM has changed:

• In the old SaaS era, billing was decoupled from usage. You signed a contract and invoices were handled by finance.
• In today’s PLG and self-serve models, the user is the buyer. Payment is integrated directly into product adoption, onboarding, and expansion.

This shift means RevOps, finance, and product need to collaborate. Payment issues aren’t just clerical—they directly impact pipeline conversion, retention, and NRR.

From Reactive Finance Problem to Proactive RevOps Lever

The key is reframing payments not as a reactive finance issue but as an opportunity to drive revenue. Vince outlines two sides of the payment equation:

Inbound Payments (customers paying you)

• Optimize UX at checkout or billing portals to reduce failures.
• Offer flexible modalities like split payments, BNPL, or ACH for B2B customers.
• View payment options as TAM expansion: flexible billing can open new customer segments.

Outbound Payments (you paying customers, partners, or users)

• Reduce friction in refunds, disbursements, and stipends.
• Eliminate reliance on slow checks and outdated reimbursement processes.
• Faster payouts = higher trust, better retention, and in some cases, a competitive differentiator.

Together, these represent a new RevOps growth lever: convert payment friction into customer loyalty, revenue recovery, and margin gains.

Case Studies: Payments as Growth Engine

• Spotify: Faced with massive revenue leakage from failed subscription payments, Spotify implemented retry logic, localized payment options, and in-app prompts. The result: millions in recovered revenue and a stronger RevOps-finance-product coalition.
• Uber: Historically, drivers waited days (or weeks) for payouts. With “Instant Pay,” Uber let drivers cash out immediately onto prepaid debit cards. This reduced support tickets, boosted satisfaction, and became a competitive differentiator when recruiting drivers.

These examples prove payments can’t be siloed—done right, they become a core GTM differentiator. For more on best practices around closing deals, including payment options, check out our webinar recording on Closing a Deal in HubSpot: Best Practices for the Final Stretch.

How RevOps Teams Can Get Started

For operators wondering how to act, Vince lays out a playbook:

1. Quantify the Problem
   • Measure churn and specifically attribute how much comes from payment failures.
   • Even 5% monthly churn compounds to nearly 50% of your base in a year.
   • Like we say in this blog post, ensuring that your opportunity amounts tie to actual received revenue—or are corrected accordingly—is crucial.
2. Listen to Customer Stories
   • Surveys don’t always reveal payment pain. Use closed-lost analysis or direct interviews to uncover real experiences.
3. Form a Churn Committee
   • Build a cross-functional coalition of RevOps, finance, and product.
   • Treat churn as a holistic issue where payment failures sit alongside product and pricing issues.
4. Expand Optionality
   • Don’t stop at reducing failure. Offer more ways to pay—whether installments, BNPL, or localized payment methods—to expand your TAM.

And also check out our prior webinar Overcome Pricing Friction to Improve the Closing and Renewal Process.

The Role of AI in Payments

Of course, no modern RevOps discussion is complete without AI. Vince is clear: AI isn’t a silver bullet, but it’s already valuable in:

• Fraud mitigation – spotting fraudulent transactions faster than humans.
• Data enrichment – identifying patterns in failed payments and predicting recovery strategies.
• Future state – AI agents guiding customers through checkout flows or proactively resolving issues before a transaction fails.

Still, Vince warns: don’t skip the basics. Ensure your systems allow customers to pay easily before over-indexing on futuristic AI use cases.

Final Takeaways

Payments are not “someone else’s problem.” They’re a core part of the customer experience, and neglecting them could mean losing half your churned customers. For operators obsessed with NRR and retention, payments may be the lowest-hanging fruit in your org:

• Reduce avoidable churn.
• Expand TAM with new payment options.
• Improve loyalty with faster, cleaner outbound flows.

“Growth isn’t just about acquisition—it’s about reducing churn. Payments are one of the most overlooked ways to do it.” – Vince Chiofolo

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