(And Why You Should… Y’know… Actually Ask Them).
Let’s set the scene: You’re about to buy or add a new line of business to your Policy Administration System (PAS). You’re on the demo call. Everything looks shiny. Everyone’s smiling. The vendor just said the word “agile” 17 times and you’re starting to believe in magic again. But here’s the catch…
They’re praying—PRAYING—you don’t ask these five questions. Because behind those polished decks and “we’re your partner” vibes is a flaming dumpster fire of half-truths and scope creep.
Here’s what they don’t want you to ask:
Question 1: “How many of your implementations actually finish on time and on budget?”
Why it scares them:
Because honest answers would expose the gap between promises and reality. According to Boost Insurance (2024), even single-product implementations take ‘six months to a year.’ Multiple products? Each one needs a separate configuration, ‘which obviously would expand the timeline.’ Translation: Your ‘6-month’ project just became a multi-year nightmare.
What they’ll say:
- “Every project is unique.”
- “It depends on the client’s readiness.”
- “Let me circle back with that data.”
What you should demand:
Numbers. Not vibes. The last 24 months of data, with names. If they dodge it, run faster than a reinsurance broker from a hurricane.
Question 2: “Can we talk to your support team before we sign?”
Why it scares them:
Because their Tier 1 support team might actually be one guy named Kevin who only works Fridays and doesn’t believe in email. Post-sale support usually transforms from “Disneyland” to “dial-up tech support in a basement.”
What they’ll say:
- “Support is world-class.”
- “We’ll introduce you after signing.”
- “You get a dedicated team!”
What you demand:
A real convo. With the real support team. Before. You. Sign. Or else you’re marrying a stranger and hoping they do laundry.
Question 3: “Show us 5-year pricing, including escalations.”
Why it scares them:
Because their Tier 1 support team might actually be one guy named Kevin who only works Fridays and doesn’t believe in email. Post-sale support usually transforms from “Disneyland” to “dial-up tech support in a basement.”
What they’ll say:
- “Support is world-class.”
- “We’ll introduce you after signing.”
- “You get a dedicated team!”
What you demand:
A real convo. With the real support team. Before. You. Sign. Or else you’re marrying a stranger and hoping they do laundry.
Question 4: “How many of your reference customers still use the original implementation team?”
Why it scares them:
Because that ‘A-Team’ from your demo? They’re long gone. You’ll get the C-Team from a temp agency who last worked on a pizza ordering app.
What they’ll say:
- “We scale our teams.”
- “Everyone’s qualified.”
- “Natural transitions occur.”
What you demand:
Retention stats. Team guarantees. And penalties if your ‘dream team’ turns into a Scooby-Doo reboot.
Question 5: “What’s your average support ticket response time 2 years post-implementation?”
Why it scares them:
Because that ‘A-Team’ from your demo? They’re long gone. You’ll get the C-Team from a temp agency who last worked on a pizza ordering app.
What they’ll say:
- “We scale our teams.”
- “Everyone’s qualified.”
- “Natural transitions occur.”
What you demand:
Retention stats. Team guarantees. And penalties if your ‘dream team’ turns into a Scooby-Doo reboot.
So… What Now?
Most vendors bank on you not asking these questions. Their business model is built on mystery and margin. But that’s not how we roll at Combined Ratio.
- We publish our pricing
- We answer these questions before the contract
- We deliver in weeks, not decades
- We don’t charge licensing fees—because we gave those the middle finger
If you’re tired of legacy software vendors playing hide-the-pricing and vanishing post-launch, come hang out with the people who actually fixed this mess.
We’re not promising magic. We’re promising reality—delivered faster than a policy quote with no underwriter.
References
- SimpleSolve (2024): Common Reasons for Insurance Software Implementation Failure
- Boost Insurance (2024): Insurance Policy Administration System Guide for 2024
- Accenture (2024): Maximizing investment in policy administration systems