Twenty years of building the infrastructure other leaders only strategize about.
AI is the tool. I’m the collaborator who’s actually shipped it.
I’m Jessell Bassett — VP of Technology with 20+ years leading AI transformation, cloud infrastructure, and global engineering teams. AIClvrColabs is built on a simple idea: pair AI with two decades of engineering leadership, and you get collaborations that actually ship.
Open to full-time executive roles — hands-on, not just strategic
How I Can Help
Full-cycle technology leadership, from AI governance to the infrastructure that makes it real.
Enterprise AI Strategy & Governance
AI roadmap ownership, responsible AI policy, and HIPAA/PCI AI compliance for regulated environments.
AI GovernanceResponsible AICompliance
Agentic AI & Platform Engineering
Multi-agent orchestration, CI/CD automation, and release engineering that cuts weeks down to minutes.
Agentic AICI/CDMLOps
Cloud Infrastructure & DevOps
AWS/Azure architecture, Kubernetes, Docker, and the uptime/latency engineering behind them.
AWSAzureKubernetes
Technology Leadership & Team Scaling
Global engineering team builds, budget ownership, and vendor management at enterprise scale.
Team ScalingBudget OwnershipVendor Mgmt
Security & Regulatory Compliance
CISO-level governance, HIPAA/PCI compliance, and risk analysis for regulated organizations.
HIPAAPCIRisk Management
WordPress at Enterprise Scale
Multi-site release automation — the exact discipline behind a 96% release-time reduction.
WordPressRelease AutomationDevOps
Technologies I Work With
AI & Machine Learning
ClaudeChatGPTGeminiLangChain
Cloud & Infrastructure
AWSAzureKubernetesDockerJenkins
Data & Integration
MySQLPostgreSQLMSSQLOracleNetSuiteSalesforce
Engineering
PythonJavaScriptNode.jsPHPAngularVue.js
Tools
JiraConfluenceFigmaBitbucket
Things I’ve Built
A selection of products and platforms I’ve designed, built, and shipped — with real business outcomes attached.
Flagship · DevOps / Release Engineering
WP Automation CI/CD Process
An API-driven release pipeline: Plesk auto-provisions each subscription, scripts generate the database and a new WordPress instance, and WordPress core updates run automatically — across 1,000+ client sites.
Plesk APIAutomated ProvisioningWordPressCI/CD
96% faster releases
HIPAA Compliance
PractisForms
A HIPAA-compliant form builder that lets patients securely complete medical and dental forms from any device — cutting manual entry and paper for the practice.
PHP / CodeIgniterMariaDBHIPAA
~$250K MRR
AI / Privacy & Analytics
Analytics Onspire Proxy
A PII-filtering proxy that strips sensitive patient and personal data before it reaches analytics reporting — the implementation behind an AI-powered HIPAA/PCI de-identification platform.
PostgresReactGCP Cloud Run
~$500K MRR
Marketing Automation
Blog Automation
An SEO tool using AI to generate localized content per client, distributed across roughly 1,200 client sites — corroborating the scale behind the WP Automation CI/CD platform.
WordPressAI ContentLAMP
~$60K saved
Certifications
AWS Certified Cloud Practitioner
Amazon Web Services
Google Foundations of Project Management
Coursera
Claude / Anthropic Certifications (5)
Claude 101 · AI Fluency · Claude Cowork · Claude for Educators · Agent Skills
Experience
VP of Technology & CISO — Onspire Health Marketing
May 2023 – Present · Charlotte, NC
Head of Software Management — ISG
Oct 2021 – June 2023 · Boca Raton, FL
VP of Technology — Web Marketing For Dentists
Aug 2016 – Aug 2020
Product Development Manager — Phunware, Inc.
Sept 2014 – Dec 2015
NBC Universal / Telemundo — Sr. Software Engineer → Director of Operations & Technology → Sr. Director of Business Technology
Feb 2006 – Apr 2014 · 8 years, 4 promotions
Skills
Leadership & Strategy
- Enterprise AI Roadmap Ownership
- Executive Stakeholder Influence
- Budget Ownership ($1.8M+)
- Vendor Management
- Cross-Functional Leadership
- Agile & SDLC
Security & Compliance
- HIPAA & PCI Compliance
- Risk Management
- Data Governance
- AI Governance & Responsible AI
What People Say
“He built and led our AI Fluency initiative, inspiring the whole team to get Claude certified and grow in that space. Any team would be lucky to have him.”
Lazaro B. Alvarez Pino
Principal Software Engineer, OpenAI/Claude — direct report
“He has a gift for translating complex technical concepts into practical, actionable guidance that people can immediately apply.”
Diane Morgan
Marketing & Messaging Strategy Leader
“He turned our daily standups into something people actually looked forward to. He was passionate about AI and introduced our team to tools like Claude that made us genuinely more productive.”
Jerilynn Panasik
Front-End Website Developer — direct report
“His knowledge of Agile methodology is deep, and his ability to handle multiple software development projects with overlapping timelines is something he manages with ease.”
Sam Kleinman
Sr. IT Business Systems Analyst, ISG
“Jessell always demonstrated great technical and business acumen in all his interactions. He would be without a doubt a great addition to any team looking to succeed.”
Frank Davila
VP Enterprise IT Operations
Selected Thinking
A sample of how I think about leadership, AI adoption, and shipping under pressure.
Leadership
The Leadership Shift from “Doer” to “Enabler”
A hard lesson from an NBC-era SVP about time, trust, and what leadership actually means.
DevOps / CI/CD
How We Turned a Six-Week Launch Into a 96% Faster Release Process
A team was six months behind on a client release. Here’s what actually fixed it — and it wasn’t the technology.
AI Governance / Leadership
AI Won’t Replace Engineering Leadership. It Will Redefine It.
The hardest part of AI was never the technology — it’s teaching people to ask better questions.
AI Governance / Metrics
Why AI Usage Percentage Is the Most Important Metric in Your Organization
The best way to make sure your company isn’t “scared” of AI — track usage like any other adoption metric.
Let’s Build Something Together
Bring the problem. AIClvrColabs brings AI, and two decades of knowing how to actually ship it.
Fort Myers, Florida
Eastern Time Zone
Note: I work with a select number of organizations and opportunities where AI transformation, cloud infrastructure, or engineering leadership is genuinely the priority. If that’s where you are, let’s talk.
Tell me about your project or opportunity