Dele is available for hire
Hire DeleDele Olowoyo
Verified Expert in Engineering
Tech Leader and Developer
Johns Creek, GA, United States
Toptal member since June 10, 2026
Bio
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
Insight Global
Agentic AI, Large Language Models (LLMs), RAG Architecture, GitHub Copilot...
Ernst & Young
Azure Cloud Services, DevOps, CI/CD Pipelines, Enterprise Platform Engineering...
McKesson
.NET, Azure DevOps, Software Architecture, CI/CD Pipelines, API Development...
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
Work Experience
Director, Engineering
2021 - 2025
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.
Technologies: Agentic AI, Large Language Models (LLMs), RAG Architecture, GitHub Copilot, Claude Code, DevOps, CI/CD Pipelines, Azure, QA Automation, Scrum, .NET Core, Java, React, Angular, Robotic Process Automation (RPA), Databricks, Machine Learning, Predictive AI, Machine Learning Operations (MLOps), Microsoft Teams, Visual Studio, GitHub, Slack, Agile Software Development, Management, Enterprise Platform Engineering, Single Sign-on (SSO), Agile, Cloud Architecture, .NET, Azure DevOps, Software Architecture, API Development, Leadership, Artificial Intelligence (AI), ChatGPT, Playwright, TypeScript, Node.js, Selenium, AI-augmented Software Engineering (AIASE), Python, SQL, PostgreSQL, Agile Leadership, Elasticsearch, n8n, AI Agent Orchestration, Business Advisory, MongoDB, OpenAI, API Integration, Advisory, Automation, IT Consulting, System Integration, Solution Architecture, Integration, Workflow Automation, AI Automation, Agentic Workflow Design, Strategy, IT Strategy, Technical Leadership, Enterprise Resource Planning (ERP), Project Management, CRM, Microservices Architecture, Digital Strategy, Microservices, Architecture, NetSuite, Headless CMS
Assistant Director, Global Tax Service Delivery
2013 - 2021
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.
Technologies: Azure Cloud Services, DevOps, CI/CD Pipelines, Enterprise Platform Engineering, Single Sign-on (SSO), Oracle Identity Management, Agile, Cloud Architecture, .NET, Java, React, Angular, Native Mobile Apps, Microsoft Teams, Visual Studio, Azure, GitHub, Slack, Google Cloud Platform (GCP), Agile Software Development, Management, Scrum, Azure DevOps, Software Architecture, API Development, ASP.NET MVC, CSS, Leadership, Selenium, SQL, Agile Leadership, Business Advisory, API Integration, Advisory, Automation, Consulting, IT Consulting, System Integration, Solution Architecture, Integration, Workflow Automation, Strategy, IT Strategy, Technical Leadership, Enterprise Resource Planning (ERP), Project Management, Microservices Architecture, Digital Strategy, Microservices, Architecture
Senior Software Engineer
2009 - 2013
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.
Technologies: .NET, Azure DevOps, Software Architecture, CI/CD Pipelines, API Development, Agile Software Development, HIPAA, HL7, Native Mobile Apps, Azure Cloud Services, Xcode, Android App Development, iOS App Development, Microsoft Teams, Visual Studio, Azure, GitHub, Scrum, Enterprise Platform Engineering, Single Sign-on (SSO), Agile, Cloud Architecture, ASP.NET MVC, ASP.NET, HTML, CSS, Leadership, SQL, Agile Leadership, API Integration, Automation, System Integration, Solution Architecture, Integration, Workflow Automation, Technical Leadership, Microservices Architecture
Software Developer
2007 - 2009
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.
Technologies: .NET, Visual Studio, Azure Cloud Services, Agile Software Development, Entrepreneurship, Enterprise Platform Engineering, Single Sign-on (SSO), Agile, Software Architecture, API Development, ASP.NET MVC, ASP.NET, HTML, CSS, SQL, API Integration, System Integration
Software Engineer
2006 - 2007
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.
Technologies: Adobe ColdFusion, .NET, ASP.NET MVC, Visual Studio, ASP.NET, HTML, CSS, SQL
Software Developer
2004 - 2006
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.
Technologies: .NET, ASP.NET, HTML, CSS, TFS, SQL
Project History
Agentic AI Workflow Platform
As a director of engineering at Insight Global, I led the enterprise-wide adoption of agentic AI workflows across federated engineering teams. I evaluated LLMs, RAG architectures, and agentic frameworks, then built repeatable engineering patterns that teams adopted confidently in production. I also partnered with engineering leadership to evolve our toolset, accelerating product release cadence from monthly to weekly. Finally, I led rapid prototyping cycles and knowledge-sharing sessions that established a culture of AI-driven experimentation.
The initiative delivered $2+ million in monthly revenue gains and positioned the organization to scale AI capabilities sustainably.
The initiative delivered $2+ million in monthly revenue gains and positioned the organization to scale AI capabilities sustainably.
Enterprise QA Transformation
At Insight Global, I transformed QA from a reactive function into an integrated engineering partner. I implemented enterprise-wide test automation by incorporating AI-assisted testing tools, including GitHub Copilot and Claude Code, improving reliability and reducing manual testing overhead. As part of this migration, we moved our entire testing framework from Selenium to Playwright, where I personally led the architecture and was hands-on with coding.
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.
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
As an assistant director at EY, I led the delivery of a cloud-native global tax B2B and B2C platform on Azure, launching it 50% ahead of schedule and 75% below budget.
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.
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
2005 - 2007
Master's Degree in Business Administration (MBA)
Kennesaw State University - Marietta, GA, USA
1999 - 2004
Bachelor's Degree in Computer Science
Georgia Southern University - Statesboro, GA, USA
Certifications
JANUARY 2026 - PRESENT
LangChain for LLM Application Development
DeepLearning.AI
JANUARY 2026 - PRESENT
Federated Machine Learning
DeepLearning.AI
JANUARY 2026 - PRESENT
Retrieval Augmented Generation (RAG)
DeepLearning.AI
MAY 2021 - MAY 2022
Certified SAFe 5 Practitioner
Scaled Agile
OCTOBER 2019 - OCTOBER 2022
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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