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Rolando D.RD

Rolando D.

AI-First Fractional CTO

€862/day
Apex, US
8-15 years

Average response time: 1 hour

About Rolando

Fractional CTO for companies that need senior technical leadership without a full-time hire. I also build ML pipelines, operations platforms, backend infrastructure for operationally complex industries. Zero-to-one is where I work best. Looking for founders and operators who know their domain and are committed to building something real.

Recent Impact:
  • Production ML: End-to-end infrastructure for a fashion subscription company—ETL pipelines, feature store, model training, serverless inference. Zero to production in weeks, not months.
  • TMF (Transportation Management Functions): The application layer that enables AI agents to perform real-world freight operations like rating, booking, and tracking.
  • Childcare Platform: The complete tech stack for an emerging startup focused on children with special needs, from idea to production.
  • Proprietary TMS: A Transportation Management System I designed and built, then ran for nearly a decade—$10M+ in shipment value, 10,000+ bookings.

Your project might be a good fit if:
  • Your architecture was built for where you were, not where you are going
  • Technical decisions are being made by default, not by design
  • You are not sure your engineering team is building the right things, in the right order
  • Investors or the board are asking technical questions nobody can answer confidently
  • Your CTO left and you need strategic direction without a six-month search
  • You feel pressure to move on AI but do not have a clear strategy yet
  • You are about to raise and do not know what a technical due diligence review will find
  • Spanish

    Native or bilingual

  • English

    Native or bilingual

  • Portuguese

    Basic

  • Italian

    Conversational

Remote only
Primarily works remotely

Experience

  • Collaboration Lab LLC
    Founder
    August 2025 - Today (10 months)
    Research Triangle Park, Durham, NC, USA
    Companies reach a point where the technical decisions that got them here are no longer enough to get them where they are going. Collaboration Lab fills that gap.

    What we bring:
    • Fractional CTO leadership: architecture, roadmap, and technical direction without the full-time hire
    • Hands-on engineering alongside strategic oversight, not just advice from a distance
    • Architecture reviews for teams with known problems and no clear path forward
    • AI strategy and implementation for companies feeling the pressure to move before they have a clear direction
    • AI-augmented planning and auditing built into every engagement: faster delivery, fewer things falling through the cracks

    Where we have built:

    • Freight logistics and transportation infrastructure
    • Subscription commerce and ML-powered recommendation systems
    • Marketplace platforms for complex operational domains
    • Franchise management and compliance systems

    Who we work best with:

    • Founders who need senior technical judgment without a six-month search
    • Companies whose architecture has outgrown their current stage
    • Teams building in operationally complex industries where generic tech consultants fall short
    AI Automation Data integration (ETL, ELT and data warehousing) IT Architecture AI Strategy
  • Falcon Freight Labs
    Co-founder/CTO
    LOGISTICS AND SUPPLY CHAIN
    August 2025 - Today (10 months)
    Building infrastructure that lets AI agents execute real-world freight operations—rate, book, and track shipments through natural language.

    • Unified interface over legacy carrier APIs (REST + SOAP)
    • MCP server enabling Claude to execute live freight functions
    • Reusable integration framework for fast carrier expansion
  • E-Commerce Subscription Fashion Service
    Founding ML Engineer
    E-COMMERCE
    June 2025 - December 2025 (6 months)
    Architected the end-to-end ML infrastructure for a fashion subscription service—from zero to production.

    • Built the ML Feature Store and engineered the feature pipeline
    • Trained and iterated XGBoost models for keep rate prediction
    • Deployed serverless real-time inference API with caching layer
    • Integrated LLMs for customer intelligence and styling context
    • Orchestrated data pipelines and ETL jobs across AWS

    Tech: AWS Glue, SageMaker, Lambda, Step Functions, DynamoDB, XGBoost, Bedrock/Claude

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Education

  • The AI Boot Camp
    UNC-Chapel Hill
    The AI Boot Camp
  • Bachelor of Arts (BA)
    Stanford University
    2009
    Bachelor of Arts (BA)

Skill set

Categories