Senior Director, Enterprise Enablement

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

📋 Description

• Drive the strategy for customer education, modernize the learning experience, and develop a comprehensive roadmap.

• Oversee and expand the Coupa University experience: provide guidance on certification tracks, AI-driven, digital-first nurture pathways, and self-paced practitioner enablement to enhance skills acquisition and product adoption.

• Collaborate with the Learning Product organization to strategize and scale training and certification offerings, while reinforcing the free-to-fee customer education approach.

• Monitor and report on the correlation between certification, training consumption and renewal rates, partner success, and customer satisfaction — establishing this as the primary metric for the function.

• Lead a team dedicated to post-sales enablement, ensuring that customer success, consultants, and support teams are equipped with value messaging, playbooks, and technical readiness needed throughout the customer lifecycle.

• Create and manage partner enablement experiences by utilizing certification paths and joint learning frameworks for key technical roles, employing AI to expedite enablement.

• Establish goals, mentor, and develop your team; ensure they utilize the shared content engine rather than creating parallel content.

• Integrate into Customer Success, Consulting, Support, and Partner planning processes (QBRs, staff meetings, planning cycles) to identify enablement demand.

• Represent post-sales and partner enablement in the quarterly content prioritization council, balancing demand with Content COE capacity.

• Take ownership of release readiness — ensure that customer- and partner-facing teams are adequately prepared for product launches.

• Direct cross-functional change management and communications for significant corporate milestones and annual planning transitions that impact the active customer base.

• Oversee the operational integrity of key learning tools and systems to facilitate enterprise enablement.

• Collaborate with Data and Analytics teams to connect post-sales enablement, certification, and training activities directly to NRR, ARR, support ticket deflection, and renewal outcomes.

• Report key business metrics quarterly for the overall function — focusing on more than just completion or activity metrics.

⛳️ Requirements

• 12+ years of experience in operationalizing enablement, GTM, or customer education strategies within enterprise software or SaaS, including at least 5 years in direct management of people managers.

• Proven track record in leading or collaborating closely with Customer teams, Customer Success, Consulting, Support, and/or Partner organizations.

• Successful history in commercializing training or certification portfolios — including packaging, pricing, and positioning offerings that yield measurable pipeline or retention impacts.

• Strong people leadership skills: demonstrated success in managing managers and enhancing team capabilities, beyond just individual contributors.

• Data literate: adept at defining and monitoring metrics that link enablement activities to renewal and retention results.

• Executive presence: capable of aligning CCO, Customer Success, Consulting, Support, and Partner leadership around a unified operating model.

• In-depth knowledge of learning operations, learning management systems, learning experience platforms, and/or tools and systems for managing and operating educational offerings.

• Bachelor's degree required; MBA or advanced degree preferred.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Flexible work hours and remote working options.

• Opportunities for professional development and continuous learning.

• Engaging company culture with team-building activities and events.