Comment by iajiboye

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Comment by iajiboye

Nowadays, it seems every new startup has a trust center and is SOC 2 compliant from day one (wink, wink Delve). What's truly happening is that AI unit economics are forcing companies to move upmarket much earlier than previous cloud and SaaS eras.

An enterprise customer will simply offer better margins compared to a self-serve one. So companies are recognizing PLG motion isn't a persistent revenue generating motion. Instead it exists more so as a product discovery and experimentation capacity with the aim to ramp you quickly towards enterprise negotiated deals.

The difficulty with this is simply unified revenue operations across blended PLG/SLG motions is complex to achieve if you did not build the commercial foundations early. The culprit varies:

1. Massive dearth of elite, world-class monetization engineers who remain in billing for the entirety of their careers; few engs stay in the billing space by choice

2. Starting with Stripe Billing (plans and subscriptions do not scale): in billing, exceptions are the rule not the exception

3. Commercial governance, command and control tooling for the fragmented revenue stack is nonexistent (it is not-uncommon to be using 8-9 platforms for your end-to-end catalog/pricing to contracting to metering to invoicing to collection to revenue recognition lifecycle)

Agents won't serve the Frankenstein mess. It is much better to have a single source of truth (i.e system of record) of commercial terms, guardrails, policies, workflows for agents to operate upon than trying to use agents as a drop in for the manual glue work monetization, billing and ops teams currently do.

I've seen this in my career at companies like Segment, Twilio, and Orb. Happy to chat more and learn about how your companies are dealing with supporting both self-serve and enterprise customers simultaneously. I don't believe any one does this superbly well!

Replies iajiboye · 2026-03-26
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