Ticketera
Launching Ticket Protection at Checkout
Turning a moment of purchase into a trusted, high-margin add-on through partnerships and phased GTM
Context
Product Type:
Ticket protection add-on at checkout
Partners:
Ticketera (event ticketing seller), Cuvro (insurance platform), Assurant (Claims Processing)
Role:
Product Lead for integrations, workflows and GTM strategy
Scope:
End-to-end product definition, partner alignment, and launch planning
The Bridge:
This was the first event ticket protection product in Puerto Rico, integrated directly into the primary ticketing platform in the market. It sat at the intersection of checkout, partnerships, and risk. The challenge was introducing a trust-based add-on at the moment of highest intent without disrupting conversion.
The Real Problem
The 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 Opportunity
Event ticketing created a clear moment of intent, but no safety net. If plans changed, users absorbed the full loss.
The Strategic Tradeoff
We faced a foundational decision:
The fear wasn’t technical failure, it was breaking trust in the most fragile moment of the purchase.
During integration, one critical edge case — event cancellations — was not fully supported.
This became a launch blocker:
“
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
We chose Option B. We treated cancellation handling as a scale problem, not a launch blocker. Blocking launch for a low-frequency edge case would have delayed demand validation and partner confidence at the moment of highest intent.
What that meant in practice:
We Deferred:
Automated Cancellations
Complex claim adjudication (Handed off to partner)
Multi-event shopping cart support
We Prioritized:
Seamless checkout integration
Clear trust messaging
To reduce risk, we launched a phased GTM:
Soft launch with a single event
Validate flow, messaging, and claims handling
Gradually expand across events
This allowed us to ship while preserving confidence across partners.
Outcome
We validated demand without compromising the core purchase experience. Once trust is broken at checkout, you don’t get a second chance; that constraint guided every tradeoff we made.
Impact:
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
This created a blueprint for monetizing trust-sensitive moments without degrading conversion
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.
What I’d Do Differently