Enterprise AI & Cloud

Christian Sinatra

Strategic Enterprise Account Director · Founder (Exit)

I sell complex technology to large enterprises and have for 20+ years at Microsoft, Salesforce, and American Express. Today my focus is helping companies put frontier AI into production.

Christian Sinatra
Experience at Microsoft Salesforce American Express
117%of quota at Microsoft in FY25 (111% in FY26)
$100M+in bookings from an industry vertical built from zero
65,000+customers in six countries at DrapeStyle, founded and sold
Speaking

On stage

Keynotes and executive sessions for customers, partners, and Salesforce's own Corporate Kickoff.

Christian Sinatra keynoting the Gaming & Hospitality Summit he founded in Las Vegas
Gaming & Hospitality Summit, Las Vegas — which I founded
Christian Sinatra delivering a keynote for Salesforce
Keynote, Salesforce
Christian Sinatra presenting at Salesforce Corporate Kickoff
Salesforce Corporate Kickoff
About

Selling like an owner

My work is finding the high-value use case inside a large company, building consensus from the engineers running the evaluation to the executives signing it, and closing deals that take many months and many stakeholders.

Between American Express and Salesforce, I bootstrapped DrapeStyle, a direct-to-consumer brand, from my garage to 65,000+ customers, won Costco as its exclusive national online partner, and sold it in 2014. That's why I start every deal with the customer's P&L, not my product sheet.

I use Claude every day to build working tools, from a Python analytics dashboard to my own account research and executive-briefing workflows. I care about AI that enterprises can trust as much as AI that performs.

Career

Where I've done it

  • 2020 – Present

    Microsoft · Client Director; Director Specialist

    Full-cycle enterprise sales across Azure, AI, and data for a book of strategic accounts. Closed a $42M enterprise agreement.

  • 2015 – 2020

    Salesforce · Managing Director; Director, Strategic Accounts

    Built a new industry vertical from zero to $100M+ in bookings and closed one of the company's largest strategic deals of the year. Chairman's Club (FY18).

  • 2006 – 2014

    DrapeStyle, Inc. · Founder & CEO (acquired 2014)

    Bootstrapped DTC e-commerce brand; exclusive national online partner to Costco.

  • 1999 – 2006

    American Express · VP, Strategic Accounts

    National partnerships with Autodesk, Staples, Office Depot, and United Rentals. President's Club; Most Valuable Player (Division).

  • 1995 – 1999

    Dana Incorporated · Regional Manager, Technology Finance

    Supported the Apple Commercial Credit Program. 2x President's Club; part of the team that earned the Malcolm Baldrige National Quality Award.

  • 1991 – 1995

    Konica Minolta · Senior Account Executive

    Closed major contracts including Six Flags Magic Mountain and the Academy of Motion Picture Arts & Sciences. 2x President's Club.

Recognition

Awards

Chairman's Club — SalesforceInvited Speaker — Salesforce Corporate KickoffDreamforce Featured AccountTop Team — MicrosoftLiving Our Culture — MicrosoftMost Valuable Player — American ExpressPresident's Club (multiple)

Let's talk.

The fastest way to reach me is email or LinkedIn.

© 2026 Christian Sinatra