Open to New Opportunities

Stephen Dellinger_

Senior Technical Support professional with 8+ years in technical operations and escalation management. At IXL Learning I served as Tier 2 escalation analyst, Privacy Compliance Officer, and sole author of the team knowledge base, averaging 150+ cases per week at 90% CSAT. I write the docs and fix the hard stuff.

150+ Cases / Week
90% CSAT
8+ Years Exp.
100+ KB Pages

Professional Experience

Senior Customer Support Analyst (Tier 2)

Jan 2025 – Present

Rosetta Stone / IXL Learning | Remote

  • Tier 2 Escalation: Part of a two-person Tier 2 team averaging 150+ cases per week across web, iOS, Android, and macOS with a 90% average customer satisfaction rating over 3 years.
  • Privacy Compliance Officer: Processed approximately 1,100 GDPR, CCPA, and related data privacy requests in OneTrust, including right-to-erasure, data access, and opt-out submissions, coordinating with legal to keep responses timely and compliant.
  • Technical Triage: Diagnosed complex authentication, performance, audio/video, and network issues using Chrome DevTools to capture logs and validate defects before escalation to Engineering.
  • Knowledge Base Owner: Built and maintain a 100+ page Confluence wiki as sole author, used regularly by Support, QA, and Engineering. Organized into escalation flows, decision trees, and platform-specific triage guides.
  • Engineering Liaison: Primary point of contact for customer-reported defects. Wrote Jira tickets with reproduction steps, DevTools log captures, and environment data that directly resulted in shipped fixes, including a platform-wide speech recognition issue affecting multiple platforms.
  • New-Hire Training: Designed and delivered the full onboarding program for incoming analysts, including a multi-week schedule and all core documentation, getting new hires to full-case productivity within 30 days.

Customer Support Analyst

Aug 2022 – Dec 2024

Rosetta Stone / IXL Learning | Remote

  • Provided Tier 1/2 technical support across web, mobile, and desktop platforms for a SaaS edtech product used by millions of consumers.
  • Identified and documented recurring product bugs, building reproducible test cases that accelerated Engineering triage.

Material Handler / Freight Operations

Aug 2020 – Aug 2022

Walmart Distribution | Mt. Crawford, VA

Service & Support Technician

Sep 2017 – Jun 2020

ITC Systems | St. Louis, MO

  • On-Site Deployment: Traveled to client sites to install and configure access management hardware for institutions including the NY Public Library and Bureau of Prisons, working within strict security and compliance requirements.
  • Board-Level Repair: Diagnosed and repaired failed circuit boards using precision soldering, returning hardware to service instead of replacing it outright.
  • Network Build-Outs: Racked servers, ran and terminated structured cabling, and configured workstations during office network migrations.
  • Hardware Commissioning: Deployed software to endpoints and ran connectivity validation tests before handing systems off to clients.

Technical Projects

Autonomous Job Application Agent

Multi-agent Python pipeline that runs hourly, scrapes 6+ job boards simultaneously, filters listings by location using the Haversine formula, scores each result 1–10 with the Claude AI API, and delivers a digest email via Gmail API. Includes a Flask dashboard with full status tracking and on-demand AI-generated resumes and cover letters. Built as a personal tool during an active job search. Runs at under $0.05 per pipeline execution.

Python • Flask • Anthropic API • Gmail API • Google Sheets API • ReportLab • Windows Task Scheduler

Windows Server Home Lab

Configured a simulated office network using Windows Server. Managed Active Directory user accounts and applied Group Policy Objects (GPO) for security baselines.

Docker & VLAN Home Lab

Self-hosted services via Docker Compose on a segmented home network with VLANs, managed through Ubuntu/Debian Linux CLI.

AI Recipe Web App [Senior Capstone]

Senior capstone project completed end-to-end following a full SDLC. Web app that generates dietary-compliant recipes via the OpenAI API based on user constraints. Formally presented and supported by a 30-page process and design paper.

Jr. Penetration Tester Path - TryHackMe [In Progress]

Working through TryHackMe Pre-Security and Jr. Penetration Tester paths using Kali Linux. Hands-on practice with network enumeration, vulnerability assessment, and exploitation fundamentals.

Home Lab [Active]

Ongoing Linux and Windows Server learning environment. Regular hands-on work with Ubuntu and other distros via CLI, with active study of Windows Server administration and Active Directory. Used as a sandbox for testing configs, breaking things, and figuring out why.

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