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The Practice

About Massoud

Massoud Ashrafi

Massoud Ashrafi

Founder & Commercial Architect

◎ Santa Monica, California

What Changes When I Walk In

+14% gross margin at Amazon through pricing redesign
$3B+ pricing portfolio built from $1.9B at GoDaddy
+50% large-deal win rate at a $9B distributor
-30% pricing exception overhead via LLM pipelines
6 pricing functions built or transformed
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I have 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. That wasn't a framework exercise. It was execution under the operating rigor Amazon demands.

At GoDaddy, I was the first pricing hire. I built the function from scratch — one person to a team of five — and scaled the pricing portfolio from $1.9B to over $3B in managed revenue. I designed the Website Builder Good-Better-Best packaging architecture that remains a core commercial vehicle for the product today. Before me, there was no pricing function. After me, there was an operating system.

At Twilio, I led pricing and monetization strategy for SaaS, API-driven, and services offerings across enterprise, SMB, and developer segments. The SMB monetization redesign drove 20% customer growth in three months. At Shutterfly, as Sr. Director of Pricing and Promotions, I applied the same diagnostic rigor to a high-volume consumer and B2B commerce platform — a multi-brand portfolio where promotional architecture and pricing governance had to be rebuilt from the ground up.

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. I ran The Win Team, which increased large-deal win rates by 50%. I negotiated $50M+ per year in recurring revenue through structured deal architecture.

I founded Ashrafi Consulting in May 2024 to bring this accumulated operating knowledge to B2B SaaS companies that need more than a slide deck — they need someone who has built pricing systems at scale, knows exactly where they break, and can execute through go-to-market alignment. 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.

Companies & Engagements

Amazon GoDaddy Twilio / Segment Shutterfly PwC Insight Enterprises
Selected Roles
2024 – Present
Founder & Principal
Ashrafi Consulting · Santa Monica, CA
2023 – 2024
Sr. Director, Pricing & Promotions
Shutterfly · Remote
2022 – 2023
Director of Pricing Strategy & Monetization
Twilio · Remote
2021 – 2022
Director of Revenue, Pricing & Profitability
PwC · Remote
2016 – 2020
Director of Pricing Strategy & Operations
GoDaddy · Scottsdale, AZ
2010 – 2014
Principal Product Manager
Amazon · Seattle, WA
1998 – 2009
VP of Profitability / VP of Pricing
Insight Enterprises · Tempe, AZ
Point of View

A manifesto against spreadsheet pricing.

For two decades, "pricing strategy" has meant a consultant delivers a slide deck, Finance builds a spreadsheet, and Sales ignores both within a quarter. That era is over. The companies winning on pricing aren't running better spreadsheets. They're running durable commercial systems with cross-functional governance, AI-augmented monitoring, and packaging architecture that adapts to how buyers actually purchase — not how the org chart says they should.

Traditional Pricing
Annual pricing review driven by Finance calendar
Discount governance via email approval chains
Packaging designed around internal product org
Strategy dies after the executive presentation
Exception management is reactive and manual
Churn is a lagging indicator found in the quarterly review
Commercial Architecture
Continuous pricing signals from deal data, usage, and churn
LLM-based monitors flag non-standard deals before close
Packaging mapped to buyer segments and value metrics
Strategy embedded in CoE, playbooks, and operating cadence
Automated governance flags outliers and patterns in real time
Cohort models surface retention signals two quarters early

A consultant gives a recommendation. An architect builds a structure that outlasts the engagement.

That is the practice.

On Structural Debt

Applying a subscription framework to a consumption product, or a per-seat model to a workflow tool, doesn't fail because the framework is wrong. It fails because nobody diagnosed why the current model was broken before picking the replacement. I've watched this happen at companies with nine-figure revenue. The cost of skipping the diagnostic is always higher than doing it.

AI as Infrastructure, Not Feature

LLM-assisted pipelines cut pricing exception analysis time by 30% in my practice. Cohort churn models flag retention signals two quarters before they show up in revenue. These are not differentiators anymore — they're baseline infrastructure. The differentiator is knowing what questions to ask the data once you have it.

Engagement Model

I work with a small number of clients concurrently. Commercial transformations require senior attention throughout — not junior execution with occasional senior review. If a project needs a team of twelve, I'm the wrong hire. If it needs one person who has done this before and can operate at the executive level, that's what I do.

The Education

B.Sc. in Industrial & Systems Engineering from USC. B.A. in Management Engineering from Claremont McKenna. Wharton Executive Education in Revenue Analytics: Price Optimization. The engineering discipline informs everything — commercial architecture is a systems problem, and I treat it like one.