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The Onboarding Trap: Why Great Trials Still Don’t Convert

Author

Chintankumar Maisuria
May 26, 2025

In partnership with

Read time: 3 minutes.

Welcome to the 123rd edition of The Growth Elements Newsletter. Every Monday and sometimes on Thursday, I write an essay on growth metrics & experiments and business case studies.

Today’s piece is for 8,000+ founders, operators, and leaders from businesses such as Shopify, Google, Hubspot, Zoho, Freshworks, Servcorp, Zomato, Postman, Razorpay and Zoom.

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Everyone obsesses over CAC. But for most PLG and trial-based SaaS companies, the real killer metric is Time-to-Value.

You can have the best product, cleanest UI, and strongest inbound engine;
But if your user doesn’t hit the first “aha” in the first 24-48 hours, they are gone.
Not because your product is bad.
But because your onboarding flow is built for education instead of momentum.

Here’s what most GTM teams get wrong:

[1] They treat onboarding like UX. It’s actually a revenue system.

Founders delegate it to product. PMs build walkthroughs.
But no one owns the business outcome: Trial-to-Paid conversion.

Your onboarding flow is a revenue funnel.

  • Every tooltip = a conversion opportunity

  • Every CTA = a psychological nudge

  • Every email = a moment to reactivate intent

It’s not a “nice-to-have.”
It’s a monetisation engine.

[2] What kills trials isn’t churn. It’s inertia.

Most trialers don’t actively leave.
They just stop moving.

The death zone:

  • Signup complete

  • Nothing happens for 48 hours

  • Trial expires

  • “Maybe later” forever

And the worst part?
You keep reporting these as “high-intent signups” in your funnel.

[3] Salesflow Case: Had Signups. But Activation Was the Real Metric.

Trial funnel at Salesflow hinges on 3 actions:

  • LinkedIn connected

  • Campaign launched

  • Responses received

If that doesn’t happen within 7 days, the product locks.

Problem: 30-40% of signups never launched a campaign.
They wanted value, but didn’t move fast enough to see it.

Fixes they tested:

  • Real-time Slack alerts to LDRs when LinkedIn isn’t connected in 2 hours

  • In-app checklists tied to sales nudges

  • Email journeys segmented by ICP, not just stage

Result: Trial activation ↑, CAC payback ↓, trial-to-paid ratio ↑

[4] The real fix: Treat onboarding like GTM ops.

  • Trigger Slack alerts based on inaction (e.g. no campaign in 24 hrs)

  • Segment follow-ups by ICP, not generic nurture flows

  • Connect product signals with human touch (Sales/CS sync)

  • Define one “activation moment” and reverse-engineer urgency

Key Takeaway

A dead trial isn’t a lost user. It’s a GTM system that failed to convert intent into motion.

Onboarding is not UI polish. It’s monetisation infrastructure.

Build it like it matters. Because it does.

That's it for today's article! I hope you found this essay insightful.

Wishing you a productive week ahead!

I always appreciate you reading.

Thanks,
Chintankumar Maisuria