[Hiring] Director of Enablement @Leena AI

Role Description

As the Director of Enablement, you will build and lead Leena AI's Enablement function from the ground up, serving three audiences from day one: internal teams (Professional Services, Solution Consultants, Customer Success, Support, and Sales), customers, and partners. You will own how people learn to deploy, configure, and adopt AI Colleagues, through in-product guides, AI-powered self-service, community, and documentation, with structured learning and lightweight accreditation only where they add real signal.

This pivotal role turns expert knowledge into scale. Today, the know-how behind a successful deployment lives in a small number of experts on calls and in Slack threads.

You will be the founding member and build an AI-first knowledge engine that captures that knowledge once, confirms it, and publishes it to every audience and to their own AI tools, so that partners deliver independently, customers reach value faster, and internal teams stop answering the same question twice.

We are seeking an AI-forward enablement leader who scales through the product, community, and automation rather than traditional training, to stand up this net-new function and drive measurable outcomes at the intersection of B2B SaaS, AI, and enterprise delivery.

Qualifications

• 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.

Requirements

• 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 (e.g., Mintlify), conversation intelligence tools (e.g., Gong), and an LMS for lightweight accreditation.
• Experience standing up an enablement function in a growth-stage or funding-constrained environment.

Benefits

• Work at the forefront of enterprise AI and automation with a company that is defining the trends in this space, not following.
• 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, and opportunities for rapid career growth.