Director of Enablement

This is a fully remote position, open to applicants in United States.

📋 Description

• Establish the enablement strategy for internal, customer, and partner audiences.

• Manage the recruitment, development, and performance evaluation of the Enablement team.

• Develop the organizational structure and capacity planning as the business expands.

• Provide system integrators and technology partners with guides, sandboxes, AI-readable playbooks, and access to community resources.

• Collaborate with Professional Services to define readiness criteria, including partner tiers and assurance taper standards.

• Create in-product guides, walkthroughs, and contextual assistance in conjunction with Product and Design teams.

• Oversee the AI-first process for capturing, synthesizing, confirming, and publishing information from calls, tickets, and threads.

• Develop playbooks, use case recipes, failure-mode libraries, and comprehensive documentation.

• Ensure content is agent-readable through structured documentation formats, such as llms.txt.

• Cultivate and expand Leena's customer and partner community, including forums, office hours, user groups, and a recipe library.

• Maintain documentation and the academy, ensuring content remains current as the product evolves.

• Work in collaboration with Product, Design, Engineering, Professional Services, Customer Success, Partnerships, and Marketing teams.

• Provide feedback on field gaps to influence the product roadmap.

• Manage team OKRs related to self-service and AI answer deflection, guide adoption, community engagement, peer-answer rates, publishing speed, time to value, and partner-led go-lives.

⛳️ Requirements

• Bachelor's degree in a relevant field from an accredited institution.

• 10 to 15 years of experience in enablement, education services, professional services, or customer success within B2B SaaS companies, with at least 5 years in a leadership role overseeing enablement or education teams.

• Proven experience in creating an enablement or community program from the ground up and scaling it across multiple audiences (internal, customer, partner) without proportionately increasing headcount.

• Direct experience in enabling system integrators or technology partners to deliver a SaaS platform, along with evidence of how readiness was validated and assessed.

• Strong track record of presenting and communicating effectively with senior internal, customer, and partner stakeholders (C-suite, VPs, Directors).

• Practical experience using AI to enhance enablement: agents or LLM workflows for content creation and maintenance, AI search and response bots over documentation, and agent-readable knowledge (e.g., llms.txt, structured docs).

• Background in launching in-product guidance (e.g., Pendo, WalkMe, Appcues, Userpilot) and implementing digital adoption programs linked to product usage analytics.

• Fluency in enterprise SaaS platforms and integrations, enabling effective collaboration with Engineering and Professional Services SMEs to transform intricate technical content into straightforward learning materials.

• Experience in building and moderating a customer or partner community (e.g., Discourse, Khoros, Slack communities) that has measurably reduced support needs or accelerated adoption.

• Exceptional abilities in written and verbal communication.

• Capability to lead by influence across Product, Engineering, Professional Services, Customer Success, Partnerships, and Marketing without formal authority over those teams.

• Proven history of connecting enablement to business results (time to value, adoption, deflection, partner revenue), rather than merely completion rates.

• Preferred: Prior experience with AI/ML products or agentic automation platforms.

• Preferred: Familiarity with HR, IT, or employee service platforms such as Workday, ServiceNow, or SAP SuccessFactors.

• Preferred: Knowledge of AI-native documentation platforms (e.g., Mintlify), conversation intelligence tools (e.g., Gong), and a Learning Management System (LMS) for lightweight accreditation.

• Preferred: Experience in establishing an enablement function in a growth-stage or funding-constrained environment.

🏝️ Benefits

• Work at the forefront of enterprise AI and automation technology.

• Create and lead a new function within Global Professional Services from the ground up.

• Collaborate with a global team of innovators developing industry-leading technology.

• Join a dynamic, innovative, and rapidly growing company.

• Competitive salary and benefits package.

• Meaningful equity opportunities.

• Potential for rapid career advancement.