Ashley Raiteri

VP Engineering | CTO who scaled AirHelp from $1M to $85M | 5 to 120+ engineers | Agentic AI in production Leading Pedagogically

Role
CTO Advisor at Retailaer
Location
Charlotte, NC, US
LinkedIn followers
500 followers
Information TechnologyView LinkedIn profile

About Ashley Raiteri

I started my career doing guidance, navigation, and control for Tomahawk cruise missiles at Raytheon. Rocket science — literally. That was my introduction to building systems where failure is not an option, and it set the bar for everything I\'ve done since.The biggest chapter was AirHelp. I joined as the founding developer, built the engineering team from 5 to over 120, and helped grow revenue from $1M to $85M. Y Combinator backed us. We deployed ML bots that automated airline compensation claims across the EU at scale. I learned what it actually takes to build an engineering org that ships fast and survives hypergrowth.That pattern — build the team, build the systems, scale both — has repeated across my career. Co-founded one of the first ITA competitors in flight search. Designed Nordstrom.ca and cut 15% from their cloud spend. Led a Lockstep through its $10M Series A to acquisition by Sage. Advised airline retailing platforms serving United, Swiss, Virgin, and Scoot. Eight startups founded or co-founded, across defense, travel, fintech, and healthcare.Right now I\'m deploying agentic AI into real production infrastructure at Kare Partners — leading revenue cycle automation where the bots handle actual patient scheduling, interviews, claims and eligibility. No demos, real code. This is the part of AI that interests me: making it work FOR my team members and customers.I\'m a practitioner. I\'ve scaled teams, shipped products, and closed the gap between \"this could work\" and \"this is in production.\" I hold a patent, a physics degree from Georgia Tech, and strong opinions about what engineering leadership actually requires.Open to VP Engineering and Staff+ conversations where the problem is hard and the team matters.

Experience

  1. CTO Advisor

    Retailaer

    Apr 2025 — Present

    Guiding technical architecture for an airline Offer and Order Management platform.Flagship clients includes Air Europa

Education

  • Georgia Institute of Technology

    Bachelor of Science, Physics

Skills

  • Algorithms
  • Javascript
  • Uml
  • Consulting
  • Mysql
  • A/B Testing
  • Css
  • Engaging Speaker
  • Ajax
  • Php
  • C++
  • SEO
  • Architecture
  • Start-Ups
  • Agile
  • Business Development
  • Soap
  • Agile Methodologies
  • Management
  • Integration
  • Scalability
  • Software Engineering
  • Soa
  • Ia
  • Architectures
  • Product Management
  • Java
  • Ruby
  • Ruby on Rails
  • Business Strategy
  • Entrepreneurship
  • User Experience
  • Requirements Analysis
  • Xml
  • Lean Process Engineering
  • Strategy
  • Linux
  • Asp.net
  • Software Development
  • Python

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Ashley Raiteri — CTO Advisor at Retailaer in Charlotte, NC, US | Unifers