Director of Enablement

Leena AI

. Define the enablement strategy across internal, customer, and partner audiences .

Posted 11/6/2026full-timeRemote • United StatesLead💰 $180,000 - $225,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in building and scaling enablement programs across diverse audiences, leveraging AI tools for content management and community engagement. Proven ability to lead cross-functional collaboration and drive measurable business outcomes through effective enablement strategies.

Highest-signal resume keywords

Enablement Strategy DevelopmentCommunity Program BuildingAI-Driven Content ManagementIn-Product Guidance ImplementationStakeholder Communication

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

EnablementEducation ServicesProfessional ServicesCustomer SuccessSaaS PlatformsAI WorkflowsContent DraftingDigital Adoption ProgramsTechnical Content SimplificationBusiness Outcome Measurement

Soft Skills

Exceptional Communication SkillsInfluential Leadership

Tools & Technologies

PendoWalkMeAppcuesUserpilotDiscourseKhorosSlackMintlifyGongLMS

Industry Keywords

B2B SaaSAI/ML ProductsAgentic AutomationHR PlatformsIT PlatformsEmployee Service Platforms

Tech Stack

Tools & technologies

ServiceNow

About the role

Key responsibilities & impact

Define the enablement strategy across internal, customer, and partner audiences
Own hiring, development, and performance management of the Enablement team
Build the org design and capacity plan as the business scales
Equip system integrator and technology partners with guides, sandboxes, AI-readable playbooks, and community access
Define readiness criteria with Professional Services, including partner tier and assurance taper criteria
Build in-product guides, walkthroughs, and contextual help with Product and Design
Own the AI-first capture, synthesize, confirm, and publish loop for calls, tickets, and threads
Create playbooks, use case recipes, failure-mode libraries, and documentation
Make content agent-readable using structured documentation such as llms.txt
Build and grow Leena's customer and partner community, including forums, office hours, user groups, and a recipe library
Own documentation and the academy and keep content current as the product ships
Collaborate with Product, Design, Engineering, Professional Services, Customer Success, Partnerships, and Marketing
Feed field gaps back to the product roadmap
Own team OKRs tied to self-service and AI answer deflection, guide adoption, community engagement, peer-answer rate, publishing speed, time to value, and partner-led go-lives

Requirements

What you’ll need

BS or BA Degree from an accredited University
10 to 15 years in enablement, education services, professional services, or customer success at B2B SaaS companies, including at least 5 years leading enablement or education teams
Direct experience building an enablement or community program from scratch and scaling it across more than one audience (internal, customer, partner) without growing headcount at the same rate
Experience enabling system integrator or technology partners to deliver a SaaS platform, including how readiness was proven and measured
Demonstrated experience presenting to and communicating effectively with senior internal, customer, and partner stakeholders (C-suite, VPs, Directors)
Hands-on use of AI to scale enablement: agents or LLM workflows for content drafting and upkeep, AI search and answer bots over docs, and agent-readable knowledge (e.g., llms.txt, structured docs)
Experience launching in-product guidance (e.g., Pendo, WalkMe, Appcues, Userpilot) and digital adoption programs tied to product usage data
Product-aware fluency with enterprise SaaS platforms and integrations, sufficient to work with Engineering and Professional Services SMEs to turn complex technical content into clear learning
Experience building and moderating a customer or partner community (e.g., Discourse, Khoros, Slack communities) that measurably deflected support or sped up adoption
Exceptional written and verbal communication skills
Ability to lead through influence across Product, Engineering, Professional Services, Customer Success, Partnerships, and Marketing without formal authority over those teams
A track record of tying enablement to business outcomes (time to value, adoption, deflection, partner revenue), not only completion rates
Preferred: Prior experience with AI/ML products or agentic automation platforms
Preferred: Experience with HR, IT, or employee service platforms such as Workday, ServiceNow, or SAP SuccessFactors
Preferred: Familiarity with AI-native documentation platforms (e.g., Mintlify), conversation intelligence tools (e.g., Gong), and an LMS for lightweight accreditation
Preferred: Experience standing up an enablement function in a growth-stage or funding-constrained environment

Benefits

Comp & perks

Work at the forefront of enterprise AI and automation
Build and own a net-new function within Global Professional Services from the ground up
Partner with a global team of innovators building industry-defining technology
Be part of a dynamic, innovative, and high-growth company
Competitive compensation
Meaningful equity
Opportunities for rapid career growth