Sales Training & Enablement Senior Manager / Director

Onboarding Experience You are the architect of the new hire journey. You'll design, manage, and continuously improve a structured 90-day onboarding program that introduces new sales team members to our sales process, product, industry, and culture. This includes building resources, cheat sheets, and role-specific guides, coordinating with regional sales leaders, and developing individualized coaching plans at the close of each onboarding cycle. Sales Playbooks & Content You'll own the creation and maintenance of our core sales content — playbooks, talk tracks, objection handling guides, competitive briefs, and process documentation. This content needs to be accurate, accessible, and alive — regularly updated to reflect what's actually working in the field. Monthly & Ongoing Training Programs You'll plan and run a recurring training calendar for the full sales organization. This includes live sessions (remote and in-person), skill development workshops, and course-based learning — covering everything from fundamentals to advanced topics as the team grows and the market evolves. This includes running the Flight School program that helps sales associates gain the skills to be successful Sales Directors. Learning Management System (LMS) You'll manage our LMS, Lessonly end-to-end: building and grading courses, tracking completion and performance, and ensuring the content library stays current and organized. Training Gaps & Continuous Improvement You'll identify what's working and what isn't by observing sales calls, analyzing metrics, gathering feedback, and working closely with sales leadership. You'll turn those insights into updated content, new programs, or process changes. Cross-Functional Projects You'll take on additional enablement projects as the business evolves — new product launches, process rollouts, cross-departmental alignment initiatives, and anything else that helps the sales team perform at a higher level.

• Prior experience in sales, sales training, or sales enablement
• Proven ability to build and manage content and programs — not just deliver them
• Strong written communication skills; you can turn complex ideas into clear, usable materials
• Comfortable owning a project from blank page to execution without heavy oversight
• Experience with a Learning Management System preferred
• Strong presentation and facilitation skills — you can hold a room (or a Google Meet)
• Able to adapt to different learning styles and personality types
• Aligned with our company values: Bright, Gritty, and Good
• Willingness to travel occasionally for in-person training initiatives