Head of Enablement - Remote Training & Playbook Leader

Portside; Atlanta (GA); Remote; USD 150,000 - 230,000; Full time

Benefits offered by this job

Competitive base salary

Fully remote work

Generous time off policy

Health, dental, and vision insurance

Professional development and careerAdv

Job summary

Portside, a cloud-based software provider for the global aviation industry, seeks a Head of Enablement to own the enablement strategy, roadmap, and budget across Sales and Customer Success. You will design onboarding and certification for AEs, SEs, BDRs, CSMs, and managers, and build playbooks, content libraries, and product-ready training.

You will partner with Product, Marketing, and Support to translate feedback into improvements, launch new products and campaigns, and scale the function with

Qualifications

• 7+ years in sales enablement, customer success enablement, or customer education in a B2B SaaS company
• Proven track record building onboarding or training programs
• Experience partnering with Sales, CS leaders, and executives
• Strong facilitation and program design skills across live, virtual, and self-serve formats
• Excellent communication; translate complex products into usable content
• Data-driven with ability to measure impact and adjust programs
• Experience evaluating or launching a modern learning platform

Responsibilities

• Own the enablement strategy, roadmap, and budget across Sales and Customer Success
• Design onboarding, training, and certification for AEs, SEs, BDRs, CSMs, and managers
• Build and maintain playbooks, battlecards, pitch decks, and content library
• Launch new products, pricing, and campaigns with clear messaging and training
• Create the CSM playbook for onboarding, adoption, renewal, and expansion
• Partner with managers on coaching and handoffs from Sales to CS
• Collaborate with Product, Marketing, and Support to turn feedback into improvements
• Evaluate enablement tooling and scale the function

Skills

Sales enablement

Customer success enablement

Customer education

Program design

Facilitation

Communication

Education

Bachelor's degree (Business/Communications/Education)

Tools

Salesforce

HubSpot

CS platform

Conversation intelligence

Job description

Portside, a cloud-based software provider for the global aviation industry, seeks a Head of Enablement to own the enablement strategy, roadmap, and budget across Sales and Customer Success. You will design onboarding and certification for AEs, SEs, BDRs, CSMs, and managers, and build playbooks, content libraries, and product-ready training.

You will partner with Product, Marketing, and Support to translate feedback into improvements, launch new products and campaigns, and scale the function with