Dele Olowoyo
Verified Expert in Engineering
Tech Leader and Developer
Johns Creek, GA, United States
Toptal member since June 10, 2026
Dele is a tech leader, builder, and advisor with 20+ years of experience driving enterprise-scale transformation and production-grade AI solutions. He delivered $2+ million in monthly revenue through agentic AI adoption, $800+ million in annual platform revenue at EY, and scaled engineering teams across multiple countries. An expert in multi-cloud environments, DevSecOps, AI governance, and platform delivery, Dele aligns tech strategy with measurable business outcomes and bottom-line growth.
Portfolio
Experience
- Software Architecture - 20 years
- Leadership - 15 years
- QA Automation - 10 years
- Artificial Intelligence (AI) - 7 years
- Machine Learning - 5 years
- Machine Learning Operations (MLOps) - 4 years
- Claude Code - 3 years
- Agentic AI - 1 year
Preferred Environment
Claude Code, Amazon Web Services (AWS), Google Cloud Platform (GCP), Agentic AI, GitHub Copilot, ChatGPT, Gemini, Databricks, Azure Cloud Services, Agile Leadership
The most amazing...
...project I've led involved deploying agentic AI products that generated $2+ million in monthly revenue gains and cut release cycles from monthly to daily.
Work Experience
Director, Engineering
Insight Global
- Championed agentic AI workflow adoption, accelerating product release cadence from monthly to daily and delivering $2+ million in monthly revenue gains.
- Led and expanded 2 engineering organizations—QA and financial engineering—managing 30+ engineers and developing multiple team members into senior and leadership roles.
- Implemented enterprise-wide AI-assisted test automation using GitHub Copilot and Claude Code, transforming QA from a reactive function into a strategic engineering partner.
- Rebuilt lower-environment data refresh process, reducing cycle time from 3 weeks to 24 hours and enabling faster, more accurate testing with real-world data.
- Partnered with the CFO to integrate agentic workflows into the Financial ERP, enhancing reporting accuracy and positioning the business to scale from $4 billion to $10 billion in revenue.
Assistant Director, Global Tax Service Delivery
Ernst & Young
- Delivered enterprise global tax platforms supporting $800+ million in annual revenue, serving clients in 7 languages across 4 countries while reducing headcount by 25%.
- Launched a global B2C tax product in half the expected time and at 75% cost savings by building a distributed team and leveraging Azure Cloud architecture.
- Improved software release efficiency by 90% by introducing Agile practices and CI/CD pipelines, increasing productivity, transparency, and delivery speed.
- Reduced enterprise client onboarding complexity by 25% by developing a secure SSO framework enabling federated identity integration and automated self-registration.
- Migrated the firm's largest clients from Azure US to the European infrastructure, achieving EU regulatory compliance and generating a 5% increase in revenue.
Senior Software Engineer
McKesson
- Acted as a lead member of the core development team that architected and developed the electronic medical record (EMR)/practice management (PM) application from infancy to market, which served the 2-to-10 physician office market.
- Designed and implemented reusable CI/CD frameworks and automation that became foundational infrastructure for product teams. Achieved CMMI Level 5 by automating the entire DevOps process, reducing deployment times from 20+ hours to under 2 hours.
- Delivered EMR mobile applications for Apple and Android from concept to market in 100 days, which was a first at McKesson, cutting client billing costs by 10% and shipping 3 months ahead of schedule.
Software Developer
AirWatch (Acquired by VMWare)
- Developed the company's custom customer service toolset used to support the IT operations and support.
- Served as a key developer in creating the flagship mobile device management application as employee number 16.
- Led developer review and collaboration sessions to elevate the overall expertise of the team.
Software Engineer
Cignify
- Converted the entire time tracking, time and expenses, and payroll modules from Adobe Coldfusion to .NET.
- Performed regular updates to all platform modules, including areas I owned for migration.
- Oversaw deployment into on-premise infrastructure.
Software Developer
OfficeClip
- Developed a new document management system that enabled enterprise customer sales.
- Owned and maintained the entire OfficeClip platform, including architecture and QA.
- Developed custom scripts to automate deployment to on-premise infrastructure.
Experience
Agentic AI Workflow Platform
The initiative delivered $2+ million in monthly revenue gains and positioned the organization to scale AI capabilities sustainably.
Enterprise QA Transformation
In parallel, I rebuilt the lower-environment testing data refresh process, cutting cycle time from 3 weeks to 24 hours and enabling faster, more accurate testing with real-world data.
This transformation improved release confidence across the organization and reduced the cost of quality at scale.
Global Tax Platform | Cloud-native B2B and B2C Launch
The platform supported 7 languages and enabled $800+ million in annual revenue. I designed a zero-downtime deployment architecture and built a federated SSO framework that reduced client onboarding complexity by 25%. I also led the migration of EY's largest clients from Azure US to European infrastructure to meet GDPR compliance requirements, unlocking a 5% revenue increase in the EU sector.
The platform served global enterprise clients across multiple industries.
Education
Master's Degree in Business Administration (MBA)
Kennesaw State University - Marietta, GA, USA
Bachelor's Degree in Computer Science
Georgia Southern University - Statesboro, GA, USA
Certifications
LangChain for LLM Application Development
DeepLearning.AI
Federated Machine Learning
DeepLearning.AI
Retrieval Augmented Generation (RAG)
DeepLearning.AI
Certified SAFe 5 Practitioner
Scaled Agile
Professional Scrum Master
Scrum.org
Skills
Libraries/APIs
API Development, React, Playwright, Node.js
Tools
GitHub, Claude Code, Visual Studio, Microsoft Teams, Slack, GitHub Copilot, Xcode, TFS, n8n, ChatGPT
Languages
HTML, CSS, Java, TypeScript, Python, SQL
Frameworks
.NET, ASP.NET MVC, ASP.NET, .NET Core, Angular, Selenium
Paradigms
Agile Software Development, Management, DevOps, Scrum, Agile, Azure DevOps, Automation, Microservices Architecture, Microservices
Platforms
Azure, Amazon Web Services (AWS), Google Cloud Platform (GCP), Oracle Identity Management, Databricks, Adobe ColdFusion
Storage
Azure Cloud Services, PostgreSQL, MongoDB, Elasticsearch
Industry Expertise
Project Management
Other
Agentic AI, Entrepreneurship, Large Language Models (LLMs), RAG Architecture, QA Automation, Enterprise Platform Engineering, Single Sign-on (SSO), Cloud Architecture, Software Architecture, CI/CD Pipelines, HIPAA, HL7, Native Mobile Apps, Android App Development, iOS App Development, Robotic Process Automation (RPA), Machine Learning, Predictive AI, Machine Learning Operations (MLOps), Scrum Master, SAFe 5, LangChain, Gemini, OpenAI, Artificial Intelligence (AI), Leadership, AI-augmented Software Engineering (AIASE), Agile Leadership, AI Agent Orchestration, Business Advisory, API Integration, Advisory, Consulting, IT Consulting, System Integration, Solution Architecture, Integration, Workflow Automation, AI Automation, Agentic Workflow Design, Strategy, IT Strategy, Technical Leadership, Enterprise Resource Planning (ERP), CRM, Digital Strategy, Architecture, Federated Learning, Headless CMS, NetSuite
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