Director of Enablement

Leena AI

1d•$180,000 - $225,000

About The Position

Leena AI is hiring a Director of Enablement to build and lead its Enablement function within Global Professional Services. The role will serve internal teams, customers, and partners, helping them learn to deploy, configure, and adopt Leena AI’s AI Colleagues through in-product guidance, AI-powered self-service, community, and documentation. Structured learning and lightweight accreditation should be used where they provide meaningful evidence of readiness. As the founding member of the function, the Director will create an AI-first knowledge engine that captures expertise from calls, tickets, and internal discussions, confirms it with human review, and publishes it as guidance for multiple audiences and their AI tools. The goal is to help partners deliver independently, accelerate customer value, and reduce repeated questions for internal teams. The role is focused on scaling enablement through product, community, and automation, with measurable business outcomes.

Requirements

Bachelor of Science or Bachelor of Arts degree from an accredited university.
10 to 15 years of experience in enablement, education services, professional services, or customer success at B2B SaaS companies.
At least 5 years leading enablement or education teams.
Direct experience building an enablement or community program from scratch and scaling it across multiple audiences—internal, customer, and partner—without increasing headcount at the same rate.
Experience enabling system integrator or technology partners to deliver a SaaS platform, including defining and measuring readiness.
Demonstrated ability to present to and communicate effectively with senior internal, customer, and partner stakeholders, including C-suite executives, VPs, and Directors.
Hands-on use of AI to scale enablement, including agents or LLM workflows for content drafting and upkeep, AI search and answer bots over documentation, and agent-readable knowledge.
Experience launching in-product guidance using tools such as Pendo, WalkMe, Appcues, or 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 subject-matter experts to turn complex technical content into clear learning.
Experience building and moderating a customer or partner community using platforms such as Discourse, Khoros, or Slack, with measurable support deflection or faster 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.
Track record of tying enablement to business outcomes such as time to value, adoption, deflection, or partner revenue, rather than only completion rates.

Nice To Haves

Prior experience with AI/ML products or agentic automation platforms.
Experience with HR, IT, or employee service platforms such as Workday, ServiceNow, or SAP SuccessFactors.
Familiarity with AI-native documentation platforms such as Mintlify, conversation intelligence tools such as Gong, and an LMS for lightweight accreditation.
Experience establishing an enablement function in a growth-stage or funding-constrained environment.

Responsibilities

Define the enablement strategy for internal, customer, and partner audiences.
Hire, develop, and manage the performance of the Enablement team, and create its organizational design and capacity plan as the business scales.
Equip system integrator and technology partners with guides, sandboxes, AI-readable playbooks, and community access so they can deliver independently.
Define partner readiness criteria with Professional Services, including partner tiers and assurance taper criteria; use role-based accreditation where it provides meaningful signal.
Build in-product guides, walkthroughs, and contextual help with Product and Design so customer administrators and internal teams can learn within the platform.
Own the AI-first process for capturing, synthesizing, confirming, and publishing knowledge from Sales and Professional Services calls, tickets, and discussions.
Develop playbooks, use case recipes, failure-mode libraries, and documentation, using agents for drafts and requiring human approval before publication.
Make content agent-readable, including through structured documentation and formats such as llms.txt, so customers’ and partners’ AI tools can answer questions.
Build and grow a customer and partner community that includes forums, office hours, user groups, and a recipe library; channel useful peer answers back into documentation and the product.
Own documentation and the academy, keeping content current as the product changes.
Partner with Product, Design, Engineering, Professional Services, Customer Success, Partnerships, and Marketing to align enablement with the product and relay field gaps to the roadmap.
Own team OKRs for self-service and AI answer deflection, in-product guide adoption, community engagement and peer-answer rate, time from call to published answer, time to value, and partner-led go-lives.