Director of Enablement - Build AI Enablement at Scale

Leena AI; United States; Remote; USD 160,000 - 220,000; Full time

Benefits offered by this job

Meaningful equity

Job summary

Leena AI is seeking a Director of Enablement to build and lead the Enablement function from the ground up, serving internal teams, customers, and partners. You will craft how teams deploy, configure, and adopt AI Colleagues through in‑product guides, self‑service, community, and docs.

You will own the AI knowledge engine 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.
• 5+ years leading enablement or education teams.
• Direct experience building an enablement or community program from scratch and scaling it across multiple audiences.
• Experience enabling system integrator or technology partners to deliver a SaaS platform.
• Demonstrated ability to influence senior stakeholders without formal authority.
• Hands‑on use of AI to scale enablement: agents or LLM workflows for content drafting and upkeep, AI search and answer bots over docs.

Responsibilities

• Define the enablement strategy across internal, customer, and partner audiences.
• Hire, develop, and manage the Enablement team; design org design and capacity.
• Provide guides, sandboxes, and playbooks for partners; define readiness criteria.
• Build in‑product guides, walkthroughs, and contextual help; enable self‑service learning.
• Own the AI‑first capture, synthesize, and publish loop for playbooks and docs.
• Grow customer and partner community; own documentation and the academy.
• Collaborate with Product, Design, Engineering, and Marketing to align enablement with product.
• Own OKRs tied to self‑service adoption, time to value, and partner go-lives.

Skills

Agentic AI

LLM-powered knowledge management

Partner ecosystem enablement

Digital adoption platforms

Community‑led growth

Education

BS or BA Degree

Tools

Pendo

WalkMe

Appcues

Userpilot

Mintlify

Gong

Job description

Director of Enablement - Build AI Enablement at Scale — Remote

Career Opportunity Signal: This is a rare founding function role — you would be the first Director of Enablement at a Gartner-recognized, high-growth enterprise AI company. Building from zero provides strong portfolio value and fast-track visibility to C‑suite stakeholders.

Compensation vs. Market: No salary is listed. Director of Enablement roles at comparable B2B SaaS companies (Series C–D, 200–800 employees) typically range from $160,000–$220,000 base in the US, plus equity. The mention of "meaningful equity" at a growth-stage AI company could add significant upside, but vesting terms and strike price should be scrutinized closely during negotiation.

Skills Developed: This role sits at the intersection of several high-demand disciplines:

• Agentic AI and LLM-powered knowledge management — an emerging and highly valued skill set
• Partner ecosystem enablement for global SIs (e.g., Deloitte, Accenture-tier partners)
• Digital adoption platforms (Pendo, WalkMe) and in-product UX
• Community-led growth strategies increasingly adopted by PLG companies

Culture & Growth Stage Signals: Leena AI appears to be in rapid international expansion (SI partnerships, enterprise focus). The role requires leading through influence without direct authority — a green flag for collaborative culture, but a yellow flag if you prefer clear org authority.

Red Flags to Watch: "Growth-stage or funding-constrained environment" in preferred qualifications signals resource constraints. As a solo founding-function leader, budget and headcount may be limited early on. Clarify team-building budget and hiring timelines in interviews.

Company Overview

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.

Team Overview: Global Professional Services

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.

Role Overview: Director of Enablement

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.

Key Responsibilities

• 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.
• 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.

Is this role fully remote or does it require being in a specific office? The job posting does not specify an office location beyond being US‑based, and the global nature of the role strongly suggests remote work is supported. Candidates should confirm remote vs. hybrid expectations directly with Leena AI during the interview process. What level of AI experience is required for this role? Hands‑on experience using AI tools to scale enablement is required — specifically agents or LLM workflows for content drafting, AI search/answer bots over documentation, and creating agent‑readable knowledge formats like llms.txt. Prior experience with agentic automation platforms is a preferred (bonus) qualification. What is the expected team size for this Director of Enablement role? This is a founding function role, meaning you will be the first hire building the Enablement team from scratch. The posting mentions owning org design and capacity planning, implying you will hire and grow the team over time. Is salary or compensation information available for this position? No specific salary range is published in the job posting. The company mentions competitive compensation and meaningful equity as part of the package, typical for a Director‑level role at a growth‑stage AI company. What enterprise platforms should I have experience with for this role? Preferred experience includes Workday, ServiceNow, and SAP SuccessFactors. For in‑product guidance tools, familiarity with Pendo, WalkMe, Appcues, or Userpilot is valuable. Knowledge of AI‑native documentation platforms like Mintlify and conversation intelligence tools like Gong is also a plus.

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