Hello.

AI Product Leader • Enterprise Software Architect • Technical Delivery Executive

Building enterprise-grade AI products that transform industries. From AI-powered FinTech platforms to intelligent logistics systems, IoT safety solutions, healthcare assistants, and enterprise commerce platforms, I specialize in leading cross-functional teams that deliver scalable digital products powered by Artificial Intelligence. With over 8 years of experience delivering mission-critical enterprise software, I bridge business strategy, product management, software engineering, and AI innovation to create products that customers love and organizations rely on.

Based in Chicago, Illinois

Let's Talk
Future

Building the Future with AI

I help organizations design, build and scale enterprise software that combines cutting-edge AI with exceptional user experiences.

My experience spans:
Artificial Intelligence & Generative AI
Enterprise SaaS Platforms
FinTech
Logistics & Supply Chain
Healthcare Technology
Internet of Things (IoT)
E-commerce
Customer Experience Platforms

Experience

Skills and
Experience

I have successfully led multidisciplinary engineering, design, AI, and business teams from product ideation through deployment, consistently improving adoption, operational efficiency, customer satisfaction, and business outcomes.

Artificial Intelligence

Large Language Models (LLMs)
Agentic AI Systems
AI Product Strategy
Predictive Analytics
AI Agents
Recommendation Engines

Enterprise Product Leadership

Product Strategy
Agile & Scrum
Go-to-Market Strategy
Product Discovery

Cloud & Engineering

Microsoft Azure
Google Cloud Platform
JIRA
Confluence

Experience

  • AI Product Manager
    Deloitte

    Led the design and deployment of an enterprise AI communication platform within a FinTech CRM ecosystem.
  • AI Technical Product Lead
    Respectmart

    Directed AI innovation for a logistics SaaS platform serving shipping businesses globally.
  • AI Delivery Lead
    Wi-Tronix

    Led enterprise AI initiatives for Class I Railroads across North America.
  • Web Platform Delivery Lead
    DeckCommerce

    Directed enterprise commerce solutions for global retail brands. Successfully improved customer experience through analytics-driven product enhancements and product roadmap execution.
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Portfolio

Latest Projects

AI Meeting Intelligence Action Tracker
Tableau, Data Visualization, AI, Model, Algo, Analysis
AI Health Symptom Triage Assistant
Tableau, Data Visualization, AI, Model, Algo, Analysis
AI Personal Finance Copilot
Tableau, Data Visualization, AI, Model, Algo, Analysis
Freighteva
Start-up
Testimonial

Client's Testimonials

Oladipo was a great addition to my scrum team! He has a fantastic attitude and hunger for knowledge that keeps him curious. Any team would be lucky to have him!

Heather Martinez
Enterprise Portfolio & Delivery Leader

I've had the pleasure to work with Oladipo as a fellow Product Owner at Deck Commerce. He is a dedicated professional who is a great team player. Oladipo has a passion for learning new things and it showed by his willingness to jump into new projects.

Maria Rayfield
Sr. Business Analyst / Sr. Product Owner, at Storable

Calm, respectful, thoughtful .... when asked to take a project on, Oladipo smiles and says, "sure!" He researches like crazy, finds stakeholders and gets it done. I really enjoyed working with him, despite the short time, and I would gladly recommend him.

Barry McCann CSP-PO
Agile SaaS Product Team Leader at Deck Commerce

Dr Dipo is an astute "TechPrenuer" whose attention for details is second to none. We worked closely at the early stage of Afridext LLC. As our Team Lead/Founder he gave a well-thought product management timeline that delivered great results and gave us amazing visibility as a startup. He managed the team well and was a great team player.

Jide Durowoju
Marketing Manager at Àkójọpọ̀
Contact

Let's Discuss Project

Get in touch

Our friendly team would love to hear from you.

    • Phone

      (312) 420-3967

    • Mail

      dipo@oladipo.tech

    • Github

      github.com/Dipsoncool

    • LinkedIn

      Oladipo Olayanju

    • Visit My Studio

      Chicago, Illinois