Executive Fluency
Clear language, realistic tradeoffs, and ROI-centered recommendations for leaders who need confident decisions.
AI Strategy • Enterprise Systems • Practical Execution
I am Ben McLendon, an MIT-trained AI strategist, enterprise technology leader, and hands-on software architect with more than 30 years of experience helping organizations navigate complex technology decisions. I work with executives to transform uncertainty into clear strategy, modern systems, and practical AI solutions that deliver lasting operational value.
AI strategy and product innovation executive education
Business-first technology translation for leaders and teams
Hands-on development across AI, workflow, web, and systems architecture
Why Ben
Most technology advisors lean toward either executive strategy or implementation detail. I bridge both. I can translate a board-level business problem into architecture, workflows, vendor decisions, automation opportunities, and the operating habits needed to keep value compounding.
Clear language, realistic tradeoffs, and ROI-centered recommendations for leaders who need confident decisions.
Hands-on software, systems, and automation experience that keeps strategy grounded in what can actually be built.
Calm decision support rooted in evidence, data, process discipline, and direct communication.
Fast iteration without losing sight of security, maintainability, adoption, and long-term business value.
What I Do
Assess opportunities, shape business cases, define governance, and move from AI curiosity to practical product and workflow roadmaps.
Design custom GPT, RAG, document, email, API, and workflow automation systems that reduce friction and improve throughput.
Evaluate, select, deploy, integrate, and manage vertical software platforms with a bias toward adoption and measurable operational value.
Align plan, people, process, security, infrastructure, data, and application choices into systems that teams can operate confidently.
Build practical internal tools and web applications using Linux, Nginx, MySQL, PHP, Laravel, HTML, JavaScript, Python, and SQL.
Coach teams through technology change with clear communication, decision frameworks, OKRs, and accountable delivery rhythms.
Education and Certifications
Recent education and certifications support a career built across enterprise IT, cybersecurity, business transformation, and hands-on engineering.
Skills
Technology leadership, IT strategy, digital innovation, technology integration, concept generation, strategic insights, and sensemaking.
Strategic planning, partner relationship management, team leadership, team building, social influence, and visioning.
Business cases, process improvement, OKRs, KPIs, budget management, P&L management, acquisitions, and continuity planning.
Project portfolio management, scope management, requirements definition, problem solving, and complex project delivery.
Cybersecurity, incident response, data privacy, privacy compliance, regulatory requirements, ITIL 4, and service levels.
Infrastructure management, IT operations, service delivery, sourcing, network architecture, systems design, and implementations.
Software architecture, web applications, Python, JavaScript, JSON, PHP, Laravel, SQL, and internal tool development.
Cloud computing, VMware, Linux, Microsoft 365, Windows Server, VoIP, and modern operational platforms.
Property management, property management systems, PropTech, software acquisition, and provider contracting.
Coaching, mentoring, public speaking, presentations, internal and external communication, and customer satisfaction.
Ventures
Beyond advisory work, I run Old Cart Technology LLC, a small independent software company where I design and build products that solve specific, meaningful problems.
The intelligence layer connecting people, processes, knowledge, and AI across an organization.
A purpose-built professional web presence for writers and authors, designed around their work and unique needs rather than a generic CMS.
An open-source, local-first memory layer for AI agents that unifies notes, structured data, session state, files, and embeddings behind one retrieval interface over MCP.
Beyond the Brief
My avocations are working laboratories for the same habits I bring to technology: understand the system, respect the material, make the idea tangible, and keep refining until it works as intended.
01 Build
Fine furniture and musical instruments, with an emphasis on sound joinery, material selection, careful finishing, and the patience to get the details right.
02 Prototype
CNC work, 3D printing, and 2D and 3D design that turn an idea into a model, a toolpath, a physical prototype, and a better next iteration.
03 Perform
Percussion, guitar, bass, and keyboards: a lifelong practice in timing, active listening, dynamics, improvisation, and knowing how each part supports the whole.
04 Frame
Composition, light, motion, and editing sharpen the ability to find the signal, shape a clear point of view, and communicate through image and story.
05 Restore
Automobile and motorcycle restorations and modifications combine diagnosis, research, fabrication, integration, and respect for how the full machine behaves.
Connect
Let’s talk through the outcome you need, the constraints around it, and the fastest practical path forward.