Director of Technology — Fully Remote Direct Hire | Senior Technology Leadership | AI Transformation

About the Opportunity

We are partnered exclusively with a well-established, globally operating organization to find a Director of Technology. This is a senior leadership opportunity for someone who started their career writing code and has grown into a technology executive who still gets their hands dirty when it counts. The organization is in an active phase of AI adoption, platform modernization, and operational transformation — and this person will lead it.

This role reports directly to senior leadership and carries real influence over the direction of the technology function.

What You'll Be Doing

• Owning the reliability, performance, and security of all platforms supporting the business — internal systems, client-facing applications, integrations, and data infrastructure
• Leading and developing an internal technology team while managing third-party vendors and consultants
• Championing AI adoption across the organization — identifying high-impact opportunities, designing and deploying agentic workflows, and establishing governance and best practices that allow teams to move confidently
• Making build-vs-buy decisions across the stack with a pragmatic, cost-conscious approach
• Guiding the ongoing evolution of the technology platform — reducing technical debt and building toward future scalability
• Partnering with non-technical departments including finance, operations, sales, and content to translate technology decisions into business outcomes

What We're Looking For

• 8+ years in technology with a clear progression from hands-on software development into leadership — you still think like an engineer
• 3+ years managing a technology team including internal developers, vendors, and infrastructure operations
• Real, documented experience implementing AI workflows or agentic automations in a business setting — not theoretical, not a side project, something you can speak to with measurable results
• Genuine enthusiasm for AI as a practical tool for making organizations run better
• Strong architectural judgment — you know when to build, when to buy, and when to leave things alone
• Hands-on mentality — this is not a pure management role and candidates who only delegate will not be the right fit
• Experience managing IT infrastructure, hosting, security, and vendor relationships at an enterprise level
• The communication skills to work across both technical and non-technical stakeholders with equal effectiveness

Nice to Have

• Familiarity with Visual Basic or similar legacy Microsoft environments with experience modernizing them toward contemporary architectures
• Experience with AI agent frameworks, LLM APIs, and workflow automation platforms in a production business context
• Background in edtech, learning technology, or professional training services
• Cloud infrastructure experience — AWS, Azure, or GCP including migration planning
• Familiarity with LMS or LXP platforms and content delivery systems

Why This Role

You will step into a modernized environment with a clear mandate — keep things running, evolve the platform, and drive AI transformation across the business. This is not a caretaker role. The organization is growing, investing, and looking for someone to help shape where technology takes them next. Fully remote with a competitive base salary, bonus, and full benefits package.

What could make you the right fit:

• Long tenures at mid-size companies, ideally services businesses
• Hands-on technical credibility on (Microsoft, .NET, SQL Server)
• Has maintained and evolved a custom application platform over multiple years
• Has done modernization but incrementally, not rip and replace
• Has started bringing AI tools into the business, not necessarily building AI products

Pay: $150,000.00 - $160,000.00 per year

Work Location: Remote