Head of Enablement

Portside•Nashville, TN

8d•Remote

About The Position

The Head of Enablement owns the enablement strategy, roadmap, and budget across Sales and Customer Success and reports results to leadership. The role designs and delivers onboarding, training, and certification for AEs, SEs, BDRs, CSMs, and front-line managers, covering product, positioning, discovery, demos, objection handling, and renewals. It also develops domain training to help team members new to aviation get up to speed quickly. The Head of Enablement builds and maintains practical playbooks, battlecards, pitch decks, and a field content library; launches new products, pricing, and campaigns with clear messaging and training; and creates the CSM playbook for onboarding, adoption, renewal, and expansion. The role trains CSMs on health scoring, business reviews, and at-risk accounts, partners with front-line managers on call coaching, and establishes a clean handoff from Sales to Customer Success. The role collaborates with Product, Marketing, and Support to turn customer feedback into product, process, and content improvements. As the function grows, the Head of Enablement evaluates enablement tools—including learning, content, and conversation intelligence platforms—and hires and manages enablement specialists. Year-one success includes reducing new sales-hire ramp to full productivity to five months from the current baseline, and achieving consistent use of new playbooks and coaching rhythms by CSMs and front-line managers, with adoption measured quarterly.

Requirements

At least 7 years of experience in sales enablement, customer success enablement, or customer education within a B2B SaaS company.
Experience leading an enablement function or major program end to end.
A track record of 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, including creating effective training for live, virtual, and self-serve formats.
Excellent communication skills and the ability to turn complex products into simple, usable content.
A data-driven approach to goal setting, impact measurement, and program adjustment.
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.

Nice To Haves

Background evaluating, procuring, or launching a modern learning management platform.
Track record as a player-coach establishing an enablement practice from the ground up.
Familiarity with aviation technology or similarly intricate B2B enterprise domains.

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.
Develop training covering product, positioning, discovery, demos, objection handling, renewals, and aviation-domain fundamentals.
Build and maintain playbooks, battlecards, pitch decks, and a field content library.
Launch new products, pricing, and campaigns with clear messaging and training for the field.
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 translate customer feedback into product, process, and content improvements.
Evaluate enablement tooling, including learning platforms, content platforms, and conversation intelligence tools.
Hire and manage enablement specialists as the function scales.
Reduce new sales-hire ramp to full productivity to five months from the current baseline.
Support consistent adoption of playbooks and coaching rhythms by CSMs and front-line managers, measuring adoption quarterly.