About Massoud

I build operating systems that translate product value into predictable revenue.

I've spent my career inside the pricing engines of companies most people only see from the outside. At Amazon, I ran pricing and commercial strategy for digital video at L7 — the level where you own the P&L and the decisions stick. The result was a 14% gross margin improvement and a 27% revenue increase while tripling the product's geographic footprint across 8 locales. That wasn't a framework exercise. It was execution under the operating rigor Amazon demands.

At GoDaddy, I was one of the first leaders brought in to build the pricing function from scratch. There was no pricing infrastructure, no packaging logic, no commercial architecture. I designed the Website Builder Good-Better-Best packaging — grounded in willingness-to-pay research and structured as a hybrid subscription system designed to acquire customers at the entry tier and expand them through usage and value realization. That architecture remains a core commercial vehicle for the product today. Over four years I scaled the pricing portfolio from $1.9B to over $3B in managed revenue. Before me, there was no pricing function. After me, there was an operating system.

At Twilio, I led pricing and monetization strategy across the full span — PLG developer self-serve, SMB, and enterprise — for SaaS, API-driven, and services offerings. I consolidated five legacy pricing models into a unified usage-based framework built around value metrics, reducing buyer friction by 40% and improving conversion by 18%. The SMB monetization redesign drove 20% customer growth in three months. At Shutterfly, as Sr. Director of Pricing and Promotions, I rebuilt the promotional architecture and pricing governance across a multi-brand consumer and B2B commerce portfolio, improving profitability by 20%.

Before the operating roles, I spent a decade at Insight Enterprises — a $9B technology distributor — as VP of Pricing and then VP of Profitability. I transitioned the company from cost-plus to algorithmic pricing, increasing gross margin by 20%. I built the Bid Desk, ran The Win Team — which increased large-deal win rates by 50% — and negotiated $50M+ per year in recurring revenue through structured deal architecture.

I founded Ashrafi Consulting in May 2024 because most pricing advice comes from people who've never owned a P&L. I have — from PLG self-serve to enterprise deal desks, from consumer subscription to B2B platform monetization. The practice deploys AI-native tooling: LLM-assisted pipelines that cut pricing exception overhead by 30%, and cohort churn models that surface retention signals before they become revenue problems. If your commercial architecture is broken, I've probably already fixed a version of it.