Is 24/7 VIP support a retention driver or a bottleneck?

We promised direct, instant 24/7 founder-led support to every new customer to stand out from larger competitors. At first, customers loved the personal attention, and our retention rates were higher than ever.

But as our user base grew, this turned into a constant stress point. Our team is now overwhelmed by midnight support tickets, resolving minor edge cases, and hand-holding users through basic onboarding. As a result, zero time is left for high-level strategy, product improvements, or scaling our marketing.

It made me realize that over-servicing customers early on builds unsustainable expectations that break the moment you try to grow.

Have you ever over-indexed on manual customer support, and how did you transition to automated or self-serve systems without upsetting your early users?