Jacob Stephens

Experience

Head of Engineering

Educational Travel Adventures | Feb 2022 - Present | Remote

• Lead engineering (one direct report) with end-to-end responsibility for architecture, operations, deployment, and on-call response across the production stack of a multi-million-dollar travel business.
• Built three Docker/Traefik Manager Sandboxes with separate application containers, a shared writable database refreshed daily, and per-manager credentials. The marketing workflow alone has produced 30+ pull requests merged by engineering.
• Built an operations console (Python, Flask, SQLite) for fleet health, deploy review, branch previews, and browser terminals, with Google sign-in, passkeys, and per-permission access. Deployed Prometheus, Grafana, and Alertmanager across 14 of the 16 hosts in the fleet.
• After a cyber-insurer's port scan found an exposed remote-desktop service, moved operator SSH for all 16 hosts onto a Tailscale tailnet with tagged ACLs, keeping staff-facing browser consoles on MFA-gated public endpoints.
• Reduced group-manifest SQL statements per request from about 2,650 to 183 with byte-identical output. A separate measurement-led index pass eliminated about 80% of measured query time on the live primary using online DDL.
• Worked a tour as a guide, then turned the guide portal into an offline-capable PWA that guides install on their phones, adding inline itinerary reading and snap-a-photo receipt upload to fix the friction seen on the tour. 77 guides filed 410 tour reports and 1,800+ expense reports (about $154K) over a 12-month period.
• Led PHP 5-to-8, MySQL 5-to-8, and CentOS-to-Rocky Linux migrations. Modernized payment integrations and ACH/NACHA workflows, including bank-account encryption, as part of a PCI compliance initiative.
• Built a deployment pipeline with dirty-worktree rejection, serialized deploys, ancestor-only refs, health checks, and rollback; validated with PHPUnit and GitHub Actions across PHP 8.1-8.4.

Web Developer and Client Support Specialist

Sharp Innovations | Nov 2021 - Feb 2022 | Conestoga, PA

• Automated SQL/PHP database migrations, reducing execution from hours to minutes; supported client websites, security fixes, and Linux server configuration.

Full-Stack Developer (Independent)

Steward Goods | Mar 2020 - Nov 2021 | Remote

• Designed and shipped a multi-tenant possessions tracker in PHP and MySQL with full frontend, backend, and deployment ownership; implemented Stripe subscription payments for client work.