Hi, I'mKen
CTO of Enduring Ventures, Revedge.ai, and End of an Era AI, driving AI-powered transformation from concept to production. Specializing in agentic AI, analytics, and scalable architecture.
About Me
Get to know me better
Leadership: Strategic leadership with expertise in turning around struggling IT departments and elevating performance to industry-leading standards.Innovation: Driving technological innovation with a cloud-first approach, custom solutions development, and implementation of cutting-edge technologies.Excellence: Commitment to meeting and surpassing security, compliance requirements, and industry standards while delivering exceptional business value.
Core Values
- Strategic Vision: I lead with purpose, aligning technology initiatives with business goals to transform underperforming IT environments into high-performing, future ready operations.
- Innovation: Champion a culture of continuous improvement and creativity, leveraging a cloud-first mindset, tailored solutions, and emerging technologies to stay ahead of the curve.
- Excellence: Pursue operational excellence by not only meeting but exceeding industry benchmarks, regulatory compliance, and cybersecurity standards.
- Accountability: Take ownership of outcomes, ensuring transparency, reliability, and integrity in every aspect of technology and execution and leadership.
- Performance Driven Culture: Drive measurable results and inspire teams to reach new heights, building IT functions that lead the industry in efficiency, agility, and impact.
- Value Creation: I am committed to delivering tangible business value through strategic technology investments that fuel growth, resilience, and competitive advantage.
Interests
- Robotics & Automation
- Internet of Things (IoT)
- Digital Transformation
- Data Analytics & Visualization
- Business Intelligence
- Edge Computing
- Smart Infrastructure
- Emerging Technologies
- Open Source Contribution
- Human-Computer Interaction
- STEM Education & Mentorship
- Technology Ethics
- Digital Accessibility
- Green IT & Sustainable Tech
Professional Experience
My professional journey and career milestones
Chief Technology Officer (CTO)
Overview:
Primary technical executive for an entrepreneurial holding company that acquires and operates lower middle market businesses. Leading AI-driven digital transformation across portfolio companies, translating business objectives into scalable product strategies that drive valuation growth, compliance, and sustainable innovation.
Key Achievements:
- Driving AI-Driven Operational Excellence: Spearhead the digital transformation of portfolio companies by integrating agentic AI workflows and intelligent automation, directly reducing manual administrative burden and operational friction
- Scalable Analytics & Claims Intelligence: Architected and deployed self-service claims analytics platforms that automate complex data reconciliation across disparate third-party administrators (TPAs), surfacing billing irregularities and actionable KPIs in real-time
- AI-Enhanced Business Processes: Modernized organizational infrastructure by digitizing legacy provider data validation, replacing inefficient print/scan/fax workflows with intuitive, self-service portals to increase data accuracy and processing speed
- Strategic Productivity Initiatives: Established organization-wide baselines and measured AI adoption success by launching enterprise Copilot training, automating call center knowledgebases, and deploying AI-assisted sales planning to optimize cross-functional delivery
- Technical Portfolio Leadership: Act as the primary technical executive, translating business objectives into scalable product strategies that drive valuation growth, enhance compliance, and foster sustainable innovation across multiple high-stakes ventures
Chief Technology Officer (CTO)
Overview:
Providing executive technology leadership across AI and technology ventures, managing engineering teams of 4-15 people per venture. Architecting scalable systems, implementing AI/ML solutions, and driving technical strategy from concept to production across revenue optimization, legal tech, and parking intelligence domains.
Key Achievements:
- Revedge.ai: Leading revenue optimization AI platform delivering measurable results for enterprise clients
- End of an Era AI: Building AI-powered estate settlement platform reducing 16-20 month process to weeks through document automation
- Neutron Parking: Parking equipment and parking intelligence platform that integrates into locations for best-in-class equipment at the cheapest TCO
- Oblige AI (through 07/2026): Led biometric authentication platform with facial recognition and voice authentication using deep learning models
- Managing distributed engineering teams across multiple technology stacks (TypeScript, Python, TensorFlow, cloud infrastructure)
- Implementing real-time systems, computer vision, NLP, and autonomous systems at production scale
Chief Technology Officer (CTO)
Overview:
Oversaw all aspects of IT, managing corporate systems, omnichannel commerce, parking lot systems (POS, Kiosks, gate automation), DevOps, software development, architecture, and eCommerce websites. Supervised mobile apps, master data management (MDM), and hybrid cloud infrastructure.
Key Achievements:
- Elevated the department to a top-performing entity, contributing to a $60 Million increase in company valuation
- Led successful migration of legacy systems to Azure and AWS, resulting in improved scalability and performance
- Architected and implemented comprehensive Azure and AWS cloud strategy with minimal business disruption
- Custom built a new POS system to replace an outdated solution, reducing costs and improving transaction speeds
- Created and trained License Plate Recognition (LPR) software using AI/ML to achieve 99.99% accuracy
- Developed the Park 'N Fly mobile app, enhancing user experience and increasing revenue
Cloud Architect, Live Services
Overview:
Formulated, maintained, and communicated a comprehensive infrastructure architecture strategy, collaborating with senior leadership and technical teams across all business units. Served as escalation manager for critical situations, ensuring swift and effective resolution.
Key Achievements:
- Spearheaded initiatives to optimize new systems securely with effective monitoring
- Guided infrastructure redesign for Sage Payments Solutions and GETI group, ensuring PCI compliance
- Established the Cloud Center of Excellence program, supporting product teams across multiple cloud platforms
- Efficiently managed cloud projects employing PaaS and IaaS models
- Led product readiness reviews, culminating in "go-live" recommendations to the SVP of IT and CIO
Principal Architect, Infrastructure Services
Overview:
Collaborated with senior leadership and technical staff across all businesses to maintain and communicate a cohesive infrastructure architecture strategy. Designed and constructed large, complex infrastructure solutions with a global user base.
Key Achievements:
- Facilitated operational and security programs, including assessments and readiness reviews
- Effectively collaborated with stakeholders to gain collective buy-in on architecture strategies
- Identified and addressed infrastructure deficiencies and led enterprise capacity planning
- Provided guidance and mentorship to fellow architects and engineers on best practices
- Assessed business and technical needs for upgrade and migration strategies
Senior Consultant/Project Manager/Enterprise Architect
Overview:
Formulated and implemented enterprise cloud technical strategies for diverse clients. Engaged in all aspects of projects from development to implementation, defining and documenting cloud solution architectures with detailed technical designs.
Key Achievements:
- Orchestrated end-to-end design and deployment of scalable and highly available services on Azure
- Developed scalable backend systems using Java and .Net for client-specific needs
- Created intricate infrastructure as code structures to enhance operational efficiency
- Established enterprise approaches for containerization, serverless computing, and API management
IT Manager/Designer/Enterprise Architect
Overview:
Implemented standardized approaches for computer upgrades and established company-wide IT policies. Delivered comprehensive IT, AV, and security designs for large-scale building projects with detailed specifications.
Key Achievements:
- Designed IT, AV, and Security systems for buildings ranging from 100k to 1m square feet
- Managed teams of up to nine individuals, tracking asset warranties across all company offices
- Upgraded and maintained DMVPN linking all sites with QOS implementation for VoIP functionality
- Successfully managed projects for prestigious clients including Shands Healthcare, St. Anthony's Hospital, and multiple universities
Professional Skills
Key capabilities that drive my professional success
Cybersecurity
Implementing robust security measures and ensuring compliance with industry standards and regulations.
Incident Response & Forensics
Responding to and investigating security incidents to protect organizational assets.
Compliance & Risk Management
Ensuring adherence to legal, regulatory, and industry standards while mitigating organizational risk.
AI & Data Analytics
Leveraging artificial intelligence and data analytics to drive business insights and automate processes.
Data Governance & Analytics
Establishing frameworks for effective data management and leveraging analytics for business intelligence.
Digital Transformation
Driving business value through digital innovation, modernization, and the adoption of emerging technologies.
Cloud Architecture
Expert in Azure, AWS, and GCP cloud platforms with experience in designing and implementing scalable cloud solutions.
IT Leadership
Strategic direction and leadership for enterprise IT organizations, managing teams and driving technological vision.
IT Operations Management
Overseeing all aspects of IT operations to ensure efficient and reliable technology service delivery.
Merger/Acquisition Integration
Successfully integrating disparate IT systems and processes during corporate mergers and acquisitions.
Project Management
Leading complex, cross-functional technology initiatives from conception through successful implementation.
IT Architecture
Designing and implementing scalable enterprise technology solutions that align with business objectives.
IT Strategic Planning
Developing and executing comprehensive IT strategies that support and advance business goals.
Budget Management
Strategic financial planning and oversight of technology budgets to maximize ROI and operational efficiency.
Application Development
Leading the design and development of custom applications to address specific business needs and challenges.
POS Systems
Expertise in designing and implementing point-of-sale systems with integrated payment processing capabilities.
DevOps & Automation
Implementing CI/CD pipelines, infrastructure as code, and automation for rapid, reliable deployments.
Vendor Management & Negotiation
Managing vendor relationships, negotiating contracts, and ensuring optimal value from technology partners.
Budgeting & Cost Optimization
Developing and managing IT budgets, identifying cost-saving opportunities, and maximizing ROI.
Disaster Recovery & Business Continuity
Planning, implementing, and testing strategies to ensure resilience and rapid recovery from disruptions.
IT Service Management (ITSM)
Delivering high-quality IT services using best practices such as ITIL and continual service improvement.
Network & Infrastructure Engineering
Designing, deploying, and maintaining robust, secure, and scalable IT infrastructure.
Application Development & Modernization
Leading full-stack application development and modernizing legacy systems for agility and performance.
User Experience (UX) & Customer-Centric Design
Championing user-focused design to deliver intuitive, impactful technology solutions.
Change Management
Guiding organizations through technology and process changes to ensure adoption and success.
Team Building & Mentoring
Developing high-performing teams, mentoring talent, and fostering a culture of growth.
Contract Management
Overseeing contract negotiation, compliance, and lifecycle management for IT services and solutions.
Stakeholder Communication
Communicating complex technical concepts to business stakeholders and executive leadership.
Process Improvement & Lean IT
Optimizing IT processes for efficiency, quality, and value through continuous improvement methodologies.
Procurement & Licensing
Managing technology procurement, software licensing, and vendor compliance.
Policy & Governance
Establishing and enforcing IT policies, standards, and governance frameworks.
Technology Roadmapping
Developing and executing technology roadmaps aligned with business strategy and goals.
Testimonials
Get In Touch
Interested in working together? Feel free to reach out.