GB

AI Founder | Delivery Leader | Army Veteran

Geoffery BabajideBuilding AI that amplifies human capability.

After 20+ years leading enterprise delivery and $2B+ in major initiatives, I built CAIJA: an AI resume analyzer that gives job seekers honest alignment scores before they apply. Now building a portfolio of human-AI hybrid solutions where AI augments, never replaces.

Explore Career JourneyView LinkedIn

About Me

From enterprise delivery leader to AI founder.

After 20 years leading enterprise delivery programs and getting auto-rejected from roles I was perfect for, I built CAIJA: an AI resume analyzer that shows you your ATS alignment score before you apply. The results: 3 interviews in 4 weeks, job search went from erratic to focused, and I feel in control again.

My philosophy: control where you need it, AI where it matters. Human in control of decisions, goals, and choices. AI in control of analysis, pattern matching, and detection. Every product I build amplifies human capability rather than replacing it. This principle is formalized through the Obsidian Realization Initiative (ORI) and the Homo Alius Manifesto.

Author of Authority Is Not Enough (in progress) and researcher behind LCAT (Leadership Cognition Augmentation Theory) and the LEAP AI delivery framework. Read more on the ORI blog.

Based in North Carolina. Currently: CAIJA Founder & CEO, Sr. Director at HRHS leading healthcare AI platform development, and Army veteran with 23 years of command experience.

Geoffery Babajide

Career Journey

Execution depth across military and enterprise systems.

2026 - Present

Founder & CEO

CAIJA (Continuous AI Job Advisor)

Founded company focused on human-AI hybrid solutions that amplify human capability. CAIJA is the first product: an AI-powered resume analyzer helping job seekers optimize their search.

  • Built AI resume analyzer that scores ATS alignment before candidates apply, with apply/tailor/skip recommendations.
  • Personal results: 3 interviews in 4 weeks, 40% reduction in wasted applications after months of auto-rejections.
  • Tech stack: FastAPI, LangChain, GPT-4/Claude, KDB.AI, Next.js. Free tier live at caija.io/analyze.
  • Company vision: portfolio of human-AI hybrid workforce solutions including interview prep, salary coaching, and career planning.

2025 - Present

Sr. Director, Strategy & Program Services Delivery

Hope Restored Human Services (HRHS)

Leading healthcare implementation portfolios spanning onboarding, integration, cutover, stabilization, and compliance-first operations.

  • Architected MAG-EHR AI Platform: Menuless AI-Guided EHR conversational navigation using FastAPI, LangChain, LangGraph, and Appwrite, reducing admin overhead by 40%.
  • Led enterprise SaaS EHR/EMR platform transition (TherapyBoss) and operational workflow redesign driven by strict HIPAA compliance.
  • Directed global teams (Engineering, Architecture, Operations) delivering customized RCM services including claims, payment posting, and eligibility verification.
  • Established portfolio governance using OKRs/KPIs, built TCO models for transparent budgeting, and led full-cycle RFPs for Massachusetts CMMS compliance.

2002 - 2025

Sr. Director of Operations (Battalion Commander, 2020 - 2022)

United States Army Reserve

Commanded 500+ personnel global medical battalion across 4 geographic regions. Transformed unit readiness from 22nd to 1st across a 2,300-soldier brigade.

  • Managed $60M+ annual budgets and directed strategic operations with mission-critical requirements and multinational coordination.
  • Architected AI prototype decision-support solutions applying HITL validation to improve operational decision-making reliability by 500%.
  • Designed and operationalized 10 Tactical Operations Centers with 3-hour rapid deployment capability.
  • Managed CPIC, TBM, FITARA federal IT portfolios supporting $60M+ budgets with cloud modernization strategies.

2024 - 2025

Director, PMO

Crayon

Rebuilt a failing PMO in 90 days, establishing enterprise governance and delivery standards across a 98-project portfolio.

  • Governed portfolio spanning insurance, regulated SaaS, and cloud transformation with OKR-aligned prioritization.
  • Improved on-time delivery by 20%+ and reduced delivery variance by 25% through standardized intake and risk escalation.
  • Delivered AI/ML fraud-scoring capabilities combining machine learning with configurable rules.
  • Embedded HIPAA, GDPR, and CCPA compliance patterns into delivery processes, reducing audit cycle time.

2023 - 2024

Sr. Program Manager, Partner Technology Transformation

Avalara

Led enterprise Partner solution initiative on Salesforce platform generating $2B in projected revenue, a critical contractual commitment for acquisition board.

  • Managed complex ecosystem integration across Salesforce Agentic AI, ServiceNow, Snowflake, SAP, and Dynamics platforms.
  • Transformed distressed programs into stable, predictable delivery environments using structured governance.
  • Built integration architecture supporting enterprise-scale partner solutions with seamless data flow.
  • Delivered company-wide critical solution establishing Avalara's position in enterprise partner ecosystem.

2018 - 2023

Consulting Managing Director / Delivery Lead

Outsourced Results Inc

Built and scaled multi-client consulting delivery organization managing concurrent healthcare, manufacturing, and government engagements.

  • Led $35M statewide SLED SaaS modernization transforming legacy infrastructure for 50,000+ users.
  • Directed SAP S/4HANA implementations for Fortune 500 clients including BASF and Ocean Spray, achieving 99%+ on-time delivery.
  • Pioneered CCPA rule interpretation validation with California stakeholders, establishing first reusable privacy playbooks.
  • Achieved 95%+ customer satisfaction across all engagements.

2009 - 2018

Sr. Manager / Engagement Manager & PMO Lead

NTT DATA North America

Directed 32-person global PMO managing 40+ programs across healthcare, P&C insurance, banking, and manufacturing sectors.

  • Managed $25M+ annual budget with consistent on-time execution, reducing delivery variance by 25%.
  • Directed $17M healthcare portfolio across major payers (BCBSNC, Tufts, Carefirst), achieving $2M in cost savings.
  • Delivered TriZetto Facets and HealthEdge implementations with 99%+ audit pass rate.
  • Implemented AI/ML model risk-scoring data feeds supporting payment integrity and claims prioritization.

Current Projects

Driving innovation across leadership, AI operations, and defense.

CAIJA (Continuous AI Job Advisor)

Founder & CEO

After 20 years of enterprise delivery and getting auto-rejected from roles I was perfect for, I built the tool I wished existed. CAIJA is a full career intelligence platform: three-dimension resume scoring (Fit, Positioning, Screen), job discovery across 19 countries, AI document builder for tailored resumes and cover letters, career memory with gap analytics, SMART goal dashboard, role discovery, and batch analysis. Built with Next.js, FastAPI, GPT-5.4, Claude Haiku 4.5, Appwrite, and Stripe. Personal results: 3 interviews in 4 weeks, 40% fewer wasted applications. Free tier live, no signup required.

Try it free

MAG-EHR AI Platform

Sr. Director, HRHS

Architected a Menuless AI-Guided EHR conversational navigation platform using FastAPI, LangChain, LangGraph, and Appwrite. Integrated KDB.AI semantic search with LangSmith observability. Deployed via Docker on DigitalOcean, reducing admin overhead by 40%.

Obsidian Realization Initiative (ORI)

Founder & Researcher

Founded ORI as the parent organization and research home for human-AI hybrid products. Authored the Homo Alius Manifesto: a 10-part declaration that human and AI intelligence occupy different functional positions, and together create additive intelligence. Developed LCAT (Leadership Cognition Augmentation Theory) and the LEAP AI delivery framework for enterprise AI project governance. Blog and LinkedIn content engine drive ongoing thought leadership. Built on trust. Powered by both.

Learn more

Authority Is Not Enough (Book)

Author

Writing a diagnostic book for experienced leaders examining why capable, well-intentioned leaders still fail quietly. Core thesis: leadership operates across two overlapping systems, the department (where authority is granted) and the group (where people decide whether leadership is safe to follow). Explores authority vs legitimacy, quiet failure, slow capture, and silence as signal. Currently in progress.

Army Strategic AI Research

Sr. Director of Operations

Architected AI prototype decision-support solutions applying Human-in-the-Loop validation to improve operational decision-making reliability by 500%. Designed command-and-control infrastructure supporting real-time intelligence fusion across distributed teams.

Core Capabilities

Built for compliance, scale, and measurable outcomes.

  • Enterprise architecture and delivery governance
  • Healthcare, payer, policy, and claims modernization
  • Cloud delivery across AWS, Azure, and GCP
  • AI governance, model risk controls, and decision intelligence
  • Regulatory alignment: HIPAA, ACA/CMS, SOX/ITGC, GDPR, CCPA
  • Large-scale PMO design, telemetry, and financial controls

Certifications

Certified SAFe 6 AgilistCertified SAFe 4 AgilistMicrosoft Certified: Azure FundamentalsITIL v3TOGAF 10 Foundation

Education

The United States Army War College (MA, Strategic Studies)Nichols College (MBA)Northeastern University (BS, Mechanical Engineering)

Trademarks & Patents

Enterprise Portfolio Management as a Service (ePMaaS)™Reg. No. 7,028,149

Top Skills

Enterprise ArchitectureAI Product DevelopmentProgram Delivery Leadership

Portfolio

Live products and initiatives.

Live

CAIJA: AI-Powered Career Advisory Platform

Full-stack career intelligence platform. Three-dimension resume scoring (Fit, Positioning, Screen) with apply/tailor/skip recommendations. Job discovery across 19 countries, AI document builder for tailored resumes and cover letters, career memory with gap analytics, SMART goal dashboard with weekly check-ins, role discovery, and batch analysis for up to 20 roles. Built with Next.js, FastAPI, GPT-5.4, Claude Haiku 4.5, Appwrite, and Stripe. Free tier available, no signup required.

Try it free

Live

Obsidian Realization Initiative (ORI)

Parent organization and research home for human-AI hybrid products. Houses the Homo Alius Manifesto: a 10-part declaration defining additive intelligence as a concrete mode of human operation. Research home for LCAT (Leadership Cognition Augmentation Theory) and the LEAP AI delivery framework. Blog covering human-AI collaboration philosophy, AI project delivery methodology, and the Homo Alius vision. Built on Trust. Powered by Both.

Learn more

Delivered

Prelegal: AI Legal Agreement Platform

Agentic AI legal agreement platform that conversationally interviews users to draft professional contracts, replacing traditional forms with an AI-guided experience. Supports 12 agreement types using templates crafted by 40+ attorneys, powered by LiteLLM for multi-provider AI (OpenAI, Cerebras). Multi-cloud Infrastructure as Code deployment across GCP (GKE Kubernetes), Azure (Container Apps), and AWS (EKS) using Terraform. Built with Next.js, FastAPI, Docker, and Kubernetes.

Blog

AI Delivery & Project Management

ai-deliveryproject-management

Why AI Projects Fail: It Is Not the Technology

Most AI project failures are not technology failures. They are delivery failures dressed up in technical language. The patterns are predictable, and the fixes are structural.

ai-deliveryhitl

Human-in-the-Loop Is Not Optional

The most reliable AI systems I have built or led all share one trait: a human validation layer at every decision point that carries real consequence. This is not a limitation. It is the architecture.

View all posts →

AI Digital Twin

Ask Geoffery's AI twin about CAIJA, his AI philosophy, and career journey.

This assistant knows Geoffery's full story: from enterprise delivery leader to CAIJA founder, his human-AI hybrid philosophy, military leadership, and 20+ years of transformation experience.

Digital Twin

I am Geoffery's AI digital twin. Ask me about CAIJA, the Obsidian Realization Initiative, my Homo Alius Manifesto on human-AI partnership, my book 'Authority Is Not Enough,' my career journey, or anything on my profile.

Powered by OpenAI (model set by server OPENAI_MODEL)

Contact

Open to strategic advisory and transformation leadership conversations.

gbabajide@gmail.com+1 (617) 669-2396linkedin.com/in/geoffbabajide