Head of Enablement

RegScale is a continuous controls monitoring (CCM) platform purpose-built to deliver fast and efficient GRC outcomes. We help organizations break out of the slow and expensive realities that plague legacy GRC tools by bridging security, risk, and compliance through controls lifecycle management. By leveraging CCM, organizations experience massive process improvements like 90% faster certification times, and 60% less audit prep time. Today’s expansive security and compliance requirements can only be met with a modern, CCM based approach, and RegScale is the leader in that space. Position: We are seeking a Head of Enablement to own the strategy, content, systems, and training that ensure every internal stakeholder, partner, and customer-facing team engaging with our product can ramp quickly and perform at a high standard, while supporting the Customer team in scaling our enablement programs to perform at a high standard. This is a high impact senior individual contributor role where you will work directly with senior executives across the business as well as our customers and partners. You will build the content, manage the supporting systems, and hold stakeholders accountable for contributing accurate, timely, and exceptional material. . Key Responsibilities: • Lead enablement strategy and content creation for internal teams, implementation partners, and resellers, including product/process training and certification programs • Partner with RegScale’s Customer team to support customer enablement, including RegScale Academy content, learning paths, and certification development • Deliver live and asynchronous training for internal teams and partners. Support the RegScale Customer team with ad-hoc customer training requests • Administer and upgrade the enablement tech stack, including Learning Management System (LMS), content authoring tools, and knowledge base • Set certification/assessment criteria, measure and report on enablement effectiveness, and address performance gaps directly • Monitor and enforce internal training expectations to ensure compliance with RegScale standards and certifications. Brief leadership on training progress and escalate any issues for remediation • Support cross-functional process improvements based on enablement feedback Required Qualifications: • 8+ years experience building enablement programs at enterprise SaaS organizations, with training spanning multiple functions, including partner and channel enablement — not solely sales enablement • Hands-on LMS administration and instructional design experience, including building certification or competency frameworks • Experience in a fast-paced enterprise SaaS organization where product and processes are continually advancing • High attention to detail, player/coach with an eagerness to be a hands-on content creator while mentoring others • Excellent written and verbal communication skills, with demonstrated executive presence • High energy, outcome-oriented work style, with a track record of measurable results • Ability and willingness to travel at least 20% of the time