Head of Enablement

Key Responsibilities

• Own the enablement strategy, roadmap, and budget across Sales and Customer Success, and report results to leadership.
• Design and run onboarding, training, and certification for AEs, SEs, BDRs, CSMs, and front-line managers, covering product, positioning, discovery, demos, objection handling, and renewals. Build domain training so team members new to aviation get up to speed quickly.
• Build and maintain playbooks, battlecards, pitch decks, and a content library the field actually uses. Launch new products, pricing, and campaigns to the field with clear messaging and training.
• Create the CSM playbook for onboarding, adoption, renewal, and expansion, and train CSMs on health scoring, business reviews, and at-risk accounts.
• Partner with front-line managers on call coaching, and build a clean handoff from Sales to Customer Success.
• Work with Product, Marketing, and Support to turn customer feedback into product, process, and content improvements.
• Evaluate and implement enablement tooling as needs grow, including whether a learning platform, content platform, or conversation intelligence tool is worth adding, and hire and manage enablement specialists as the function scales.

What Success Looks Like in Year One

• New sales hires ramp to full productivity in 5 months, down from today's baseline.
• CSMs and front-line managers are using the new playbooks and coaching rhythm consistently, with adoption measured quarterly.

Qualifications

• 7+ years of experience in sales enablement, customer success enablement, or customer education within a B2B SaaS company, including leading a function or a major program end to end
• Proven track record building onboarding or training programs that improved ramp time, win rate, or retention
• Experience working with Sales and Customer Success leaders, front-line managers, and executives
• Strong facilitation and program design skills, able to build effective training with simple tools across live, virtual, and self-serve formats
• Excellent communication skills, with the ability to turn complex products into simple, usable content
• Data-driven approach to setting goals, measuring impact, and adjusting programs
• Experience with a CRM such as Salesforce or HubSpot and a CS platform or conversation intelligence tool
• Bachelor's degree in Business, Communications, Education, or a related field
• Background in evaluating, procuring, or launching a modern learning management platform is preferred
• Track record as a player-coach establishing an enablement practice from the ground up is a strong plus
• Familiarity with aviation tech or similarly intricate B2B enterprise domains is a strong plus

What We Offer

• Competitive base salary
• Fully remote work
• Generous time off policy
• Health, dental, and vision insurance
• Opportunities for professional development and career advancement.
• Dynamic, collaborative, and fast-growing work environment.