Head of Enablement

Portside; United States; A distancia; USD 140.000 - 180.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Fully remote

Time off policy

Professional development

Career growth

Descripción de la vacante

Portside is seeking a senior Sales/Customer Success Enablement leader to define and execute the enablement strategy across Sales and CS. You will own the roadmap, budget, and training programs for AEs, SEs, BDRs, CSMs, and managers, creating playbooks, decks, and a content library that the field actually uses.

You will collaborate with Product, Marketing, and Support to translate customer feedback into product and process improvements, implement new tooling as needed, and scale the function with

Formación

• 7+ years in sales enablement, customer success enablement, or customer education within a B2B SaaS company
• Proven track record building onboarding or training programs
• Experience with Sales and Customer Success leaders and executives
• Strong facilitation and program design skills for live, virtual, and self-serve formats
• Excellent communication skills translating complex products into simple content
• Data-driven approach to goals, impact measurement, and adjustments

Responsabilidades

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

Conocimientos

Enablement strategy

Sales enablement

Program design

Facilitation

Communication

Data-driven

CRM experience

Aviation tech familiarity

Educación

Bachelor’s degree in Business/Communications/Education

Herramientas

Salesforce

HubSpot

CS platform

Learning platform

Conversation intelligence

Descripción del empleo

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.