Director of Technical Training

About the Role

The organization is seeking a visionary leader to build and scale a modern, AI-driven technical content and enablement engine. This role will establish the Technical Training team as the primary source for all technical education, creating a modular content library organized around core capabilities such as AVD, Windows 365, Intune/UEM, application management, Auto-scale, image management, and automation. The goal is to assemble this library into persona- and solution-based learning paths. A customer and partner enablement roadmap will be developed, spanning onboarding, certification, self-serve learning, and technical deep-dives, packaged for various delivery methods including self-paced courses, a knowledge base, virtual live training, instructor-led sessions, Masterclasses, and partner enablement programs.

Responsibilities

• Build and scale a modern, AI-driven technical content and enablement engine.
• Establish the Technical Training team as the single authoritative source for all technical education, building a modular content library organized around core capabilities that can be assembled into persona- and solution-based learning paths.
• Develop a customer and partner enablement roadmap spanning the full lifecycle and package it for multiple delivery contexts.
• Educate and certify enterprise customers by building dedicated learning paths and certification programs for customer IT admins and leaders, delivered through various channels.
• Partner with Product and Engineering to translate new features and architecture changes into practical guidance for customers and internal teams.
• Co-own the partner and MSP technical education strategy by building a collaborative operating model with the Partner Enablement lead and extending it to MSP partners through train-the-trainer programs.
• Connect training and enablement to revenue by building the measurement infrastructure to answer key business questions regarding the impact of education on deal closure, renewal rates, win rates, and support ticket volume.
• Define KPIs, integrate data sources, build cohort comparison frameworks, and report revenue-linked results to executive leadership.
• Coordinate all technical education and enablement across the company by chairing a cross-functional Education Council to maintain a unified education calendar, align on content priorities, and eliminate redundant or competing events.
• Identify enablement gaps and prioritize content and training that reduce friction and support volume.
• Lead the team as a hands-on leader who can build strategy and coach execution simultaneously, setting goals and measuring impact.
• Embed content creation into the product development cycle by establishing processes with Product and Engineering to ensure early access to roadmap information and a defined role in the release process.
• Feed recurring themes, confusion points, and technical gaps from learners back to Product and Engineering to influence roadmap and documentation.

Qualifications

• 8+ years in technical training, customer education, or enablement within a B2B SaaS or technology company, with at least 3 years in a leadership role managing a team of 5+.
• Demonstrated experience building a scalable customer or partner education program from early-stage to measurable maturity.
• Experience with localization requirements.
• Track record of tying education and enablement programs to business outcomes with real data.
• Experience operating in a dual-motion business (direct + channel) and building programs that serve both.
• Strong cross-functional leadership and influence skills, having aligned Product, Sales, Partner, Support, and CS/Marketing teams as a peer.
• Microsoft Cloud background.
• Hands-on experience with a modern LMS (preferred) and familiarity with content production workflows, certification design, and learning path architecture.
• Excellent written and verbal communication skills, with the ability to simplify complex technical concepts for multiple audiences and formats.

Preferred Qualifications

• Hands-on experience with similar platforms; certifications in Microsoft Azure or Modern Workplace technologies.
• Experience with persona-based or solution-based curriculum design.
• Experience building measurement pipelines that connect LMS data to CRM and product usage data.
• Experience building or scaling an LMS, self-serve knowledge base, or customer learning academy from the ground up.

Benefits

• Competitive Base and Incentive Plan
• Stock Options
• Health and Welfare Plans
• Life and Disability Plans
• Retirement Plan
• Unlimited Flexible Paid Time Off, including your birthday off
• Collaborative Team Culture

* Benefits for international employees, outside the US, vary by country.