Remote Enablement Lead - Strategy, Training & Adoption

Portside; Raleigh (NC); Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

Fully remote work

Generous time off policy

Health, dental, and vision insurance

Professional development and careerAdv

Job summary

Portside is seeking a senior enablement leader to shape the onboarding, training, and certification programs for Account Executives, SEs, BDRs, and Customer Success teams. You will create the playbooks, content library, and messaging needed to launch new products and campaigns.

You will partner with Product, Marketing, and Support to translate customer feedback into improvements. You will drive CSM onboarding, health scoring, and strategic coaching, while building scalable enablement tooling and

Qualifications

• 7+ years in sales enablement, customer success enablement, or related B2B SaaS roles.
• Proven onboarding/training program experience improving ramp and metrics.
• Experience partnering with Sales leaders, CS leaders, and executives.
• Strong facilitation and program design skills across formats.
• Excellent written and verbal communication for simple content.
• Data-driven goals, measurement, and program adjustment.
• Experience with Salesforce or HubSpot and CS tools; familiarity with learning platforms.
• Bachelor's degree in Business, Communications, Education, or related field.
• Player-coach enabling practice from the ground up is a plus.
• Familiarity with aviation tech or complex B2B domains is a plus.

Responsibilities

• Own enablement strategy, roadmap, and budget across Sales and CS.
• Design onboarding, training, and certification for AEs, SEs, BDRs, CSMs, and managers.
• Build playbooks, battlecards, decks, and a content library used by the field.
• Launch new products, pricing, and campaigns with clear messaging.
• Create CSM playbook for onboarding, adoption, renewal, and expansion.
• Train CSMs on health scoring, business reviews, and at-risk accounts.
• Coach front-line managers and ensure clean handoffs from Sales to CS.
• Turn customer feedback into product/process/content improvements.
• Evaluate enablement tooling and hire/manage specialists as needed.

Skills

Sales enablement

Program design

Training leadership

CRM (Salesforce/HubSpot)

Data-driven

Communication

Cross-functional collaboration

Aviation knowledge

Education

Bachelor's degree in Business/Communications/Education

Tools

Salesforce

HubSpot

CS platform / conversation intelligence

Job description

Portside is seeking a senior enablement leader to shape the onboarding, training, and certification programs for Account Executives, SEs, BDRs, and Customer Success teams. You will create the playbooks, content library, and messaging needed to launch new products and campaigns.

You will partner with Product, Marketing, and Support to translate customer feedback into improvements. You will drive CSM onboarding, health scoring, and strategic coaching, while building scalable enablement tooling and