Craig 'Craole' Cole — Profile

About Me

Music is my first love. It shaped most of my adult life, long before software did. I played keyboards, guitar, and bass with the church choir and band as a teenager, but bass is the one I fell for and chose as my primary instrument. By my late teens I'd formed my own singing group.

For fifteen to twenty years, music was the center of my life. I played and worked with Skygrass (formerly Blu Grass in the Sky), No-Maddz, Stone Dub, Protoje & The Indiggnation, and BLACK as COLE, a reggae/neo-soul/jazz fusion project I founded to give a collective feeling a shape. As founder, I flexed every creative and production skill I had, wearing hats from manager to producer, web developer, videographer/director, and photographer, experience that quietly prepared me for everything that came later. My creative instincts have always run past music into performance, writing, design, and photography: anything that turns an idea into something real.

Technology was always there too, a steady countermelody running alongside the music. My first job was teaching Microsoft Office to working professionals. From there I moved into computer repair, started IT studies at Northern Caribbean University, and took a shift role in WINDALCO's Kirkvine powerhouse lab. It was chemistry work, not tech, but it paid me to work well past midnight and taught me I do my best thinking outside a 9-to-5 rhythm. Later, I studied Music Performance (Jazz) at the Edna Manley College of the Visual and Performing Arts while holding down full-time Tier 1 networking support, working nights to make both worlds fit.

Eventually I made a deliberate choice to step back from professional music and move into business process outsourcing, starting as an agent and earning a promotion into training and development within three months. From there, my path split three ways: BPO (support, learning and development, business intelligence), TEFL (freelance and with Fluentbe), and now software, data, and AI engineering.

None of it feels like dissonance. It's the same motif, just returning in a new arrangement: learn a system deeply, communicate clearly, build something useful. What moved me about music was never just the performance itself, it was watching it land, seeing a room change because of something I helped create. That's the same thing that pulls me toward this work now: an idea, built into something real, that actually adds value to someone's life. Code is just another instrument for the same purpose.

Professional Background

English as a Second Language Specialist

Freelance and Fluentbe · July 2021 – Present

• Earned TEFL certification and joined Fluentbe in May 2022; continue to freelance independently, though at a reduced pace.
• Delivered 5,000+ remote learning sessions to roughly 1,800 students across 30+ nationalities as an independent freelancer.
• Prepared learners for IELTS, TOEFL, job interviews, presentations, and high-stakes business meetings.
• Built structured, goal-oriented learning environments through targeted coaching and feedback.

Business Intelligence Specialist & Training/Quality Coordinator

NKCS · June 2019 – February 2021

• Designed, implemented, and maintained BI tools and CRM systems across departments.
• Analyzed business requirements, operational processes, and KPIs to identify improvement areas.
• Launched and oversaw a Training and Quality department during startup operations.
• Designed and delivered leadership, skills, BI-tool, and CRM-system training programs.

Learning & Development Officer

HGS · October 2016 – June 2019

• Promoted from process trainer into leadership and professional development.
• Supported design, testing, implementation, and local rollout of a global LMS.
• Built development programs aligned to organizational goals and identified training gaps.
• Trained leaders and brand advocates in leadership, facilitation, Microsoft Office, customer experience, and sales strategy.
• Contributed to the technical and creative design of forms, dashboards, and print media.

Process Trainer / Technical Support Brand Advocate

HGS · September 2015 – January 2017

• Started as an agent and was promoted to process trainer within three months.
• Coached production teams through targeted training and quality-improvement initiatives.
• Participated in Kaizen events to reduce technical-support error rates.
• Supported Internet, VoIP, and networking issues for Global Capacity and Megapath customers.
• Maintained a 98% matriculation-to-production rate across five training cohorts.

Technical direction

• Rust-first software development with Leptos, Axum, SQLite, SQLx, and command-line tooling.
• Nix-based reproducible development environments.
• Linux operations, deployment, monitoring, recovery, and documentation.
• Data engineering, business intelligence, automation, and local-first workflows.
• AI applications, LLM workflows, agent tooling, and local inference.
• Python and JavaScript as supporting languages for code comprehension, debugging, and extension.

Education and training

• Level 5 TEFL Certification, 168 hours — The TEFL Org, 2022.
• Mediation Training, 40 hours — Dispute Resolution Foundation of Jamaica, 2014.
• Music Performance (Jazz) — Edna Manley College of the Visual and Performing Arts, 2014.
• Caribbean Secondary Education Certificate — Manchester High School, 2000.

Current portfolio evidence

• Craole.CC: Rust/Leptos/Axum/SQLite portfolio application with a tracked Markdown/TOML content source, validation, static export, SQLx checks, CI, versioned releases, and deployment to a Linux host.
• TheOracle operations: documented Linux hosting, Tailscale administration, Caddy reverse proxying, systemd services, backups, monitoring, and recovery procedures.

Working approach

I value finished, documented, tested systems over large collections of unfinished experiments. My goal is to make software useful to its audience and understandable to the person who has to maintain it.