Head of Enablement

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

About Portside

Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently.

About Portside

Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently. Backed by leading technology investors Vista Equity Partners and Insight Partners, Portside is entering an exciting phase of growth. We are expanding our platform, investing in AI driven innovation, and building a global team focused on shaping the future of aviation technology.

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.