Rakshan Syed

Rakshan Syed

Division CIO, Resource Industries | Caterpillar Inc. | Enterprise Technology & AI-Driven Transformation | Board Advisor | Founder, Embolden Women

Embolden Women Global Movement•Peoria, Illinois, United States

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Experience28+ Years
LevelLeadership

Executive Overview

I help organizations navigate complex digital landscapes and turn ambitious strategies into measurable results. I have 25+ years of experience guiding companies through digital transformation, SaaS adoption, ERP modernization, AI-driven automation, and large-scale integrations, always with an eye toward delivering tangible business impact.I recently earned a certificate in AI Strategies for Business Transformation from the Kellogg School of Management at Northwestern University, deepening my expertise in applying AI and generative AI to drive strategy, productivity, innovation, and measurable business outcomes.From accelerating enterprise AI initiatives to streamlining ERP and CRM deployments, my work consistently reduces costs, improves adoption, and strengthens operational resilience. Throughout my career, I have consistently delivered results that speak for themselves:Accelerated 182 AI-driven system integrations, cutting dealer readiness by 18 weeks and enabling $1.6B+ eCommerce growth.Directed 40+ ERP migrations and M&A integrations, reducing dealer costs by 40% while modernizing global digital platforms.Revitalized stalled digital initiatives into MVPs 9× faster and at 6.8× lower cost, scaling eCommerce to $1.6B+ and driving $55M+ in savings.Whether leading a $100M+ digital program, integrating acquisitions, or enabling global SaaS transformations, my goal is to ensure technology serves the business, and the people driving it, at its fullest potential. I am always eager to connect with professionals who believe in the power of technology to drive transformation. If you’re interested in collaborating or discussing how we can drive innovation together, feel free to reach out. Let’s connect and explore the possibilities for impactful change.

Career Timeline

Professional employment history
  • Oct 2025–Present· 1 yr
    • Founder, BusinessCurrent
      Oct 2025–Present
  • Jun 2000–Present· 26 yrs 4 mos
    • Chief Information OfficerCurrent
      2026–Present
    • Director, Digital Product
      Nov 2023–Dec 2025
    • Senior Manager, Digital Product
      Nov 2021–Oct 2023
    • Manager, Digital Products
      Apr 2020–Oct 2021
    • Manager, Commercial
      Nov 2019–Mar 2020
    • Senior Program Manager
      2017–Oct 2019
    • Program Manager, Digital
      Apr 2014–Dec 2017
    • Lead, Team Operations
      Apr 2011–Mar 2014
    • Early Career - multiple positons Project Mgr, Deployment Mgr, Application Analyst
      Jun 2000–Mar 2011
  • 1998–May 2000· 2 yrs 4 mos
    • Graduate Public Service Intern
      1998–May 2000

Education

Master of Science - MS

Management Information Systems, General

University of Illinois Springfield

Bachelor of Laws - LLB

Law

Bangalore University

Associate's degree

Interior Design & Architecture

Exterior Interiors (p) LTD - Jenson & Nicholson

Executive Relationship Map

Reports To
Rakshan Syed
Vice Chair & President
Chief Financial Officer
Chief Technology Officer
Chief Operating Officer

Executive Network Preview

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Skills & Expertise

20 of 20 skills
Platform Modernization StrategyEnterprise Technology LeadershipCloud Transformation & Enterprise ArchitectureAI & Generative AI StrategyIT Strategy & Roadmap ExecutionPortfolio & Investment PrioritizationMatrix Leadership & InfluenceCybersecurity & Compliance OversightData Governance & Enterprise AnalyticsERP/CRM Modernization (Cloud-Based Ecosystems)SaaS & Digital Platform DevelopmentDigital Transformation & Enterprise ModernizationExecutive Leadership & Value CreationIntelligent Automation & AI EnablementERP ModernizationAI Strategy & Technology GovernanceVendor & Contract ManagementSoftware Engineering LeadershipTechnology Governance & Risk ManagementData & Analytics Enablement