Director of Enablement

🕒 Yesterday

🇺🇸 United States – Remote

💵 $180k - $225k / year

⏰ Full Time

🔴 Lead

👔 Director

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Leena AI

WebsiteLinkedInAll Job Openings

201 - 500 employees

🤖 Artificial Intelligence

🤝 B2B

👥 HR Tech

Artificial Intelligence • B2B • HR Tech

Leena AI is on a mission to empower enterprises to transform employee experiences using conversational AI. Their platform covers all employee touch points, from onboarding to offboarding, by automating tasks such as answering policy-related questions and managing employee tickets. By allowing organizations to listen to their employees proactively, Leena AI enhances employee engagement and enables strategic focus for HR teams. The company supports integrations with over 100 platforms, servicing more than 350 customers globally, including large enterprises like Nestlé, Puma, and Coca-Cola.

📋 Description

• 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

• 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

• 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

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