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 Hub.

Spot 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. 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.