Ticketera

Launching Ticket Protection at Checkout
Turning a moment of purchase into a trusted, high-margin add-on through partnerships and phased GTM.

Why this case study applies beyond insurance

This project reflects a common challenge in modern platforms: introducing a trust-based add-on at the moment of purchase, where timing, clarity, and confidence matter more than feature completeness. The patterns here apply to any product that sits at the intersection of checkout, partnerships, and risk.

Context

Product Type:

Ticket protection add-on at checkout

Partners:

Ticketera (event ticketing seller), Cuvro (insurance platform), Assurant (claims processing)

The shift:

Role:

Scope:

Product lead for integrations, workflows, and GTM strategy

End-to-end product definition, partner alignment, and launch planning

This was the first event ticket protection product in Puerto Rico, integrated directly into the largest (and primary) ticketing platform in the market.

The Problem

What the opportunity looked like:
Event ticketing created a clear moment of intent — but no safety net. If plans changed, users absorbed the full loss.

The real challenge:
Launching a trust-based product in a live checkout flow required alignment across:

  • Multiple companies

  • Compliance constraints

  • Payment systems

  • Customer expectations

Any friction or delay risked breaking the core purchase experience.

The Strategic Tradeoff: Completeness vs. Launch Timing

During integration, one critical edge case — event cancellations — was not fully supported.
This became a launch blocker.

We faced a decision:

Option A: Delay launch until all scenarios are fully handled

  • Lower risk exposure

  • Missed market window

Option B: Launch without cancellation handling, prioritize it post-launch

  • Accept limited exposure

  • Validate demand and GTM

I chose Option B.

I analyzed historical event data and found that cancellations were low-frequency events, while purchase intent was high. Blocking launch for a rare scenario would cost more than managing it as a follow-up.

Execution: What Shipped

  • Seamless ticket protection flow integrated into Ticketera checkout

  • Stripe integration for payments

  • Partner handoff to Assurant for claims processing

  • Clear customer communication to maintain trust

To reduce risk, I proposed a phased GTM:

  1. Soft launch with a single event

  2. Validate flow, messaging, and claims handling

  3. Gradually expand across events

This allowed us to ship while preserving confidence across partners.

Outcome

  • Launched Puerto Rico’s first ticket protection product

  • Projected to protect 200K+ tickets per year

  • Created a new recurring revenue stream for Ticketera and partners

  • Established a repeatable model for future marketplace add-ons

What I’d Do Differently

With more time, I would have automated cancellation handling earlier — not because it blocked launch, but because it became the next scale constraint once adoption grew. The initial data validated the decision, but earlier automation would have reduced operational overhead sooner.