Director of Learning Delivery & Experience

About Pragmatic Institute

Pragmatic Institute is the leading provider of product, marketing, and AI-driven training for professionals and organizations around the world. Our mission is to help teams build better products and bring them to market more effectively through industry-leading education, certifications, and resources.

About the Role

Pragmatic Institute is seeking a Director of Learning Delivery & Experience to own scheduling, capacity planning, instructor talent management, and the end-to-end client experience across our training delivery team. This is a hands-on role: you'll set direction and clarify responsibilities across the broader operations team, but in the early stages of this role you'll be doing most of the work yourself.

You'll own scheduling and capacity planning for public and private training, working directly with sales and marketing as new requests come in. You'll manage utilization, pay, performance, hiring, and certification for our instructors — both full-time and contractor — and build new capabilities to support a growing pool of contractor talent. You'll also direct the moderator team that supports live delivery and owns the client's experience in training from beginning to end, and you'll oversee event logistics for in-person sessions.

We're looking for someone who can jump in and execute right away, is comfortable operating within an existing process, and is equally comfortable building a new one where none exists yet. Experience with an LMS — we use Docebo — and the technical ability to configure and edit directly in the platform are highly valuable.

Key Responsibilities

Scheduling

• Own scheduling for public and private training, coaching, implementation, and other client-facing sessions
• Serve as the direct interface for sales and marketing on new scheduling requests and time blocks, including webinars and other marketing sessions
• Block time for training program development, including new course development

Capacity Planning

• Forecast and plan capacity across public and private delivery
• Set and maintain the public schedule across in-person and virtual formats

Instructor Talent Management

• Manage utilization, scheduling, and load balancing for instructors across both full-time and contractor talent
• Operationalize contractor instructor hiring, performance, and offboarding
• Oversee instructor training and certification to teach new courses
• Build new capabilities and processes to support a growing pool of contractor instructors alongside full-time instructors

Team Direction & Process Ownership

• Own the client's learning experience in live training, from beginning to end
• Direct the moderator team, who sit in on live sessions to keep training running smoothly, troubleshoot issues in real time, and document process feedback — likely with a team lead handling day-to-day coordination
• Oversee behind-the-scenes session and course setup, certification delivery, private event roster management, and ongoing improvement of Docebo processes and views based on team feedback
• Direct event logistics for live courses, including travel budgeting, catering, contracts, and shipping materials for in person and virtual trainings
• Clarify and coordinate responsibilities across the broader operations team, while directly handling much of the day-to-day work personally in the early stages of the role
• Operate effectively within standard processes while building new ones where they don't yet exist

Required Qualifications

• Experience managing scheduling and/or operations for a services, training, or education business
• Experience with a learning management system; Docebo experience strongly preferred
• Experience with event management and travel planning for corporate events
• Comfortable configuring and editing directly within an LMS or similar operational tool
• Experience managing instructor, contractor, or comparable talent pools, including performance management and pay calculation
• Demonstrated ability to build new processes from scratch as well as operate within existing ones
• Strong organizational and cross-functional communication skills, comfortable interfacing directly with sales and marketing
• Willingness to be hands-on and execute directly, particularly in the early stages of the role

Preferred Qualifications

• Experience managing a mix of full-time and contract/contractor talent
• Experience building or improving scheduling tools or capacity-planning systems
• Familiarity with point-based or similar instructor compensation systems
• Hands-on experience administering Docebo specifically
• Background in professional training, education, or professional services