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In this inaugural episode of Thank You for Vibe Pricing, Chargebee’s new series on scaling AI monetization, we are joined by Aisling O’Reilly, Head of Pricing at Intercom.
Aisling talks about: Intercom’s complete pricing overhaul and why they risked multi-millions in ARR in the short run to chalk out a path of durable, customer-first growth, how they designed Fin’s pioneering outcome-based model (and chose it over a usage-based variant), the operational readiness that allowed them to price for AI resolutions, how and why Intercom PMs are evolving into more commercial GMs, how the future of outcome-based pricing will likely capture even more nuanced forms of value, and so much more.
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Chapters:
(00:00) Episode highlights
(01:41) Episode intro
(03:53) A “sink-or-swim” pricing moment
(06:55) Origins of Fin’s pioneering model
(09:56) A CTO-led transformation
(13:16) Being ready for pricing outcomes
(15:55) Is a dollar too expensive?
(18:48) Inventive predictability unlocks
(22:57) A bet on falling infra costs
(26:15) “It took that one PM”
(30:27) No perfect pricing model
(32:51) Outcomes beyond outcomes
(37:25) The intersection of product and pricing
(41:34) Strong-minded finance teams
(45:09) The problem with (cost-plus) AI credits
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Referenced:
Pricing AI agents: What does ‘value-based pricing’ really mean for AI?
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Connect with Aisling:
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Connect with Vinay:
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Connect with Ariela:
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About Chargebee:
Chargebee builds foundational billing infrastructure for the dynamic, fast-scaling AI-era business models — from seats and usage, to agents, outcomes, and hybrid structures. Built for product, finance, and GTM teams that treat monetization as a growth lever.
2 episodes
