Director of Technology

LearnQuest•Philadelphia, PA

About The Position

We are looking for a Director of Technology to lead LearnQuest's technology function. This person will ensure operational reliability across our infrastructure and platforms, drive AI adoption and agentic workflow implementation across business departments, and guide the continued evolution of our technology stack in partnership with consultants and a strong internal development team. The ideal candidate has progressed from a hands-on software engineering background into technology leadership, and brings both the technical depth to make sound architecture and build-versus-buy decisions and the management experience to lead teams, coordinate vendors, and drive results across the organization.

Requirements

8+ years in technology roles with a career progression from hands-on software development into technology management and leadership.
At least 3 years managing a technology team or department, including oversight of internal developers, third-party vendors, and infrastructure operations.
Strong software engineering foundation with the architectural judgment to make sound build-versus-buy and platform decisions, even when managing rather than writing code day-to-day.
Demonstrated experience implementing AI-powered workflows or agentic automations in a business environment, with measurable operational impact.
Experience managing IT infrastructure and operations, including hosting, security, vendor relationships, and service-level management for enterprise clients.
Experience guiding technology platform evolution, including coordinating between ongoing operations and new platform initiatives.
Strong communication skills with the ability to work across non-technical departments, identify workflow opportunities, and translate technology decisions into business terms.

Nice To Haves

Experience with AI agent frameworks, LLM APIs, and workflow automation platforms in production business contexts.
Background in learning technology, edtech, or training services, with familiarity with LMS/LXP platforms and content delivery systems.
Familiarity with Microsoft technology stacks (.NET, VB) and experience evolving them toward contemporary architectures.
Cloud infrastructure experience (AWS, Azure, or GCP), including migration planning and cloud-hosted environment management.
Experience in a services business where technology supports revenue-generating operations with enterprise client commitments.

Responsibilities

Own the reliability, performance, and security of all systems supporting LearnQuest's learning business-internal platforms, client-facing systems, integrations, hosting, and data infrastructure.
Manage IT operations, including coordination with third-party infrastructure and managed services vendors, ensuring SLA compliance and cost efficiency.
Oversee the ongoing maintenance, enhancement, and support of the current application stack, managing the development team responsible for day-to-day application operations, bug resolution, feature requests, and system stability.
Lead the internal technology team: set priorities, maintain standards, manage resource allocation, and develop talent.
Maintain technology governance including documentation, change management, incident response, and security and compliance practices.
Champion AI adoption across the business by identifying high-impact opportunities to apply AI and agentic workflows in sales, operations, finance, content development, and client services.
Design and deploy agentic AI solutions where AI agents can plan, execute, and iterate on multi-step business processes with appropriate human oversight.
Evaluate and implement AI tools, platforms, and APIs for internal use, balancing capability with cost and complexity.
Establish AI governance, usage guidelines, and best practices that enable confident and responsible adoption across teams.
Guide the ongoing evolution of LearnQuest's technology platforms, working with third-party consultants and the internal development team to prioritize improvements, reduce technical debt, and strengthen the foundation for future growth.
Make build-versus-buy decisions across the stack, evaluating custom development, third-party platforms, and SaaS solutions against total cost of ownership and strategic fit.
Support product leadership in evaluating and integrating learning technology platforms, providing technical perspective on feasibility, integration, and cost.
Ensure infrastructure supports the company's expanding AI enablement capabilities, including API integrations, data pipelines, and platform extensibility.