TOSHON JENNINGS v2.0
PEOPLE-CENTERED TECHNOLOGIST, EDUCATOR, & ADVOCATE
Professional Summary
Creative IT professional with experience managing multi-campus infrastructure and data security.
Skilled in asset management, incident response, service delivery, and automation.
CompTIA Security+ and ITIL v4 certified, with a foundation in front-end development and user-centered design.
Builder and steward of CAps, a keyboard-first correction utility that streamlines autocorrect workflows.
Mentor and trainer of future tech professionals.
Applicable Experience
THE CITY SCHOOL · Philadelphia, PA · Sep 2022–Present
I.T. Coordinator · Aug 2023–Present
- Directed configuration and service management improvements across campuses
- Managed local administrator permissions and policy controls via Active Directory, ensuring secure access across domain devices
- Optimized asset tracking with AssetTiger; improved incident response protocols
- Instituted Raiseaticket; increased satisfaction and reduced resolution times
- Built documentation knowledge base, cutting resolution time by 2+ hours
- Monitored network threats using Google Admin & Darktrace
- Saved thousands through Chromebook repair initiative (48 devices restored)
- Facilitated elementary Chess Club (Fall & Winter)
- Applications: AssetTiger, Google Admin, GoGuardian, Microsoft Admin/Office 365, Raiseaticket, Brivo, Vonage, Rediker/PlusPortals, Wireshark
Teacher · Jan 2023–Jul 2023
- Co-taught Responsive Classroom for 1st grade, integrating educational tech
- Managed tech delivery; improved student engagement
- Facilitated elementary Chess Club
- Applications: IXL, Rediker/PlusPortals
Teacher Aide · Sep 2022–Dec 2022
- Supported kindergarten instruction with technology-enhanced lessons
CAPS™ · Input Correction Utility · Creator & Product Steward · Jul 2025–Present
- Architected and distributed CAps™, a cross-context keyboard utility for fixing double-capitalization errors
- Designed cockpit interface with sticky headers, favicon parity, and anchor-linked FAQs
- Refined UX and visual polish across homepage, onboarding, and verification guide
- Documented triggers, use cases, and technical notes for cockpit transparency
- Open-sourced project with licensing, version control, and trust-forward framing
- Tech stack: AutoHotkey v2, GitHub/Pages, HTML/CSS/JavaScript, Markdown
CERT-READY TECHNOLOGY ACADEMY, LLC · Philadelphia, PA · Founder & Managing Director · Jun 2025–Present
- Launched a career-focused tech academy for middle school, high school, and adult learners
- Designed certification-first pathways for students to earn industry credentials alongside diplomas
- Developed curriculum aligned to CompTIA, Microsoft, and other certifying bodies
- Built partnerships to expand access to tech careers and serve underrepresented communities
- Led instructional strategy, platform selection, and outreach initiatives
SAY YES TO EDUCATION · Philadelphia, PA · Program Assistant · Nov 2011–Jun 2018
- Tutored and mentored MS, HS, and college students across subjects
- Collaborated with faculty/staff to design academic interventions (FERPA compliant)
SANKOFA FREEDOM ACADEMY CHARTER SCHOOL · Philadelphia, PA · Mathematics Instructor · Oct 2015–Jun 2017
- Taught Honors Algebra I/II, Pre-Algebra; improved test scores and performance
- Facilitated SAT Prep and Chess Clubs (MS/HS)
- Applications: PowerSchool, Khan Academy, IXL
Credentials
- A+ (220-1101) — CompTIA · In Progress
- A+ (220-1102) — CompTIA · Jul 2023 · ID: 454739851
- ITIL 4 Foundations — Mar 2024 · ID: 9980075910883929
- Network+ — CompTIA · In Progress
- Security+ — CompTIA · May 2022 · ID: COMP001021956324
- Certified Coach — GoGuardian · Apr 2024
Education
- Western Governors University — B.S./M.S. in IT Management (In Progress)
- NexGenT — Cyber Security Specialist (480-hour NISP Program)
- Thinkful — UX/UI Design Certificate
General Toolkit
- Design: Figma, Adobe, Canva, typography, accessibility, UX research
- Security: Wireshark, Nmap, AWS, GoGuardian, Linux, OSINT
- Programming: PowerShell, Bash, Python, HTML, CSS, JS, SQL, XML, MD
- Knowledge Management: Obsidian, Logseq, Notion, Scrivener, Whimsical
- Chess Tools: Chess.com, DecodeChess, Stockfish
AI Fluency & Toolkit Architecture
- Actively leverage multiple AI platforms for creative, technical, and research workflows, including:
- Text-based intelligence: GPT-4 (including custom GPT creation), Claude Sonnet, Microsoft Copilot, GitHub Copilot, NotebookLM, Gemini/AI Studio, Perplexity, Grok
- Visual generation: Leonardo, DALL·E, Sora
- Asset and documentation support: Albus
- Expertise in prompt engineering for productivity, troubleshooting, research acceleration, and instructional design
- Design and deploy custom GPTs for workflow automation, onboarding, and interactive documentation
- Cross-model comparison for AI reliability, retrieval fidelity, and UX friction identification
- Steward AI interactions with cockpit-aligned markup, respecting user clarity and visual parity
CONTACT
Last updated July 30, 2025 · For full cockpit projects or contact info, see About Toshon.