Director of Enablement

Leena AI is a leading agentic AI platform for the enterprise back office, helping organizations transform their employee experience at scale. Our AI Colleagues move beyond simple chatbots to act as autonomous, specialized digital coworkers that resolve HR, IT, finance, and procurement requests end to end, integrating across systems such as Workday, SAP SuccessFactors, ServiceNow, and Salesforce. Leena has been recognized as a Leader in its category by Gartner for three consecutive years and partners with global enterprises to bring agentic AI to the center of their digital transformation initiatives.

The Global Professional Services team, also known as the Implementation and Managed Services group, is responsible for deploying Leena AI's AI Colleagues across our enterprise client base. This team owns the entire delivery process, from post-sale handoff through go-live and into steady-state customer success, and collaborates closely with Product and Engineering to ensure every deployment lands successfully. As Leena expands through system integrator and technology partners, Global Professional Services is building a net-new Enablement function so that internal teams, customers, and partners can deploy and adopt AI Colleagues with confidence.

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.

• Enablement Strategy & Team Leadership: Define the enablement strategy across internal, customer, and partner audiences. Own the hiring, development, and performance management of the Enablement team, and build the org design and capacity plan as the business scales.
• Partner Enablement & Readiness: Give system integrator and technology partners the guides, sandboxes, AI-readable playbooks, and community access to deliver independently, with lightweight, role-based accreditation only where it adds real signal. Define readiness criteria with Professional Services, including partner tier and assurance taper criteria.
• In-Product Guidance & Self-Service: Build in-product guides, walkthroughs, and contextual help with Product and Design, so customer admins and internal teams learn inside the platform at the moment they need it, without depending on Professional Services for every question.
• AI Knowledge Engine: Own the AI-first capture, synthesize, confirm, and publish loop that turns Sales and Professional Services calls, tickets, and threads into playbooks, use case recipes, failure-mode libraries, and documentation, using agents for first drafts and a human approving everything before it publishes. Make content agent-readable (e.g., llms.txt, structured docs) so customers' and partners' own AI tools answer questions before a person is asked.
• Community & Public Knowledge: Build and grow Leena's customer and partner community (forums, office hours, user groups, a recipe library) so peers answer each other and the best answers flow back into docs and the product. Own documentation and the academy, and keep content current as the product ships.
• Cross-Functional Partnership: Partner with Product, Design, Engineering, Professional Services, Customer Success, Partnerships, and Marketing to keep enablement in step with a fast-moving product and to feed field gaps back to the roadmap.
• Performance & OKR Ownership: Own team OKRs tied to 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.

Required Qualifications

Education:

• BS or BA Degree from an accredited University.

Professional Experience:

• 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).

AI-Centric Enablement Expertise:

• 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.

Communication & Leadership:

• 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 Qualifications

• 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.

Why Join Leena AI?

• 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.