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
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
CTO Advisor
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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