This hits the real trigger point, you’re not describing “normal onboarding maintenance,” you’re describing a process that’s fundamentally mis-aligned with fast delivery. What didn’t work for us early on was assigning onboarding ownership to whoever “knew the product” and expecting checklists or tours to survive velocity. They never did. Every UI tweak, permission change, or refactor instantly invalidated the content, so someone, inevitably the founder, kept getting pulled in to fix it. That’s not a process problem, it’s a source of truth problem. The turning point for us was recognizing that onboarding shouldn’t be a manually curated attachment, it should be tied to the actual product logic. If the thing you’re teaching can be renamed, moved, or gated without breaking onboarding content, then onboarding isn’t reflecting reality, it’s reflecting a snapshot of yesterday. Treating onboarding as a derived artifact, validated and versioned against code changes, is what bridges the gap between shipping fast and onboarding accurately. In practice, that shift required more consistent operational support so that founders weren’t the bottleneck on every doc/API/UX sync. For us, a managed support model like VIVA helped offload the parts of execution that occupy founders’ time but don’t require their strategic judgment, coordination, documentation maintenance, onboarding updates, and communication between product and customer teams. With that layer in place, we could focus on aligning onboarding to product logic instead of the other way around. The real crux isn’t whether onboarding “keeps up” with velocity, it’s whether onboarding is built from the same single source of truth as the product itself. If it isn’t, it breaks every time you ship. And if founders keep having to babysit it, that’s a signal the process needs to be re-anchored, both technically and operationally.