Director Learning and Enablement (RapidScale)

Cox Enterprises • Raleigh, NC

4d • Hybrid

About The Position

At RapidScale, exceptional technology is powered by exceptional people. As a growing leader in secure, reliable managed cloud solutions, we help mid-market through enterprise organizations simplify IT and unleash innovation. With a broad portfolio spanning AWS, Azure, and Google, as well as a full suite of Private Cloud and Cybersecurity solutions, RapidScale enables companies to turn technology into their greatest competitive advantage. Backed by the strength of the Cox family of companies, we offer best-in-class benefits, a commitment to work-life balance, and an award-winning workplace experience. Our consulting practice empowers clients to optimize cloud investments, modernize operations, and drive measurable business outcomes. At RapidScale, part of the Cox family of businesses, we’re hiring a Director of Learning & Enablement to architect and execute an enterprise learning ecosystem that empowers the business to thrive. As a strategic leader within a fast-paced MSP environment, this role is responsible for the end-to-end strategy, design, and delivery of professional development programs that drive performance, scalability, and customer satisfaction. Reporting to the COO, the ideal candidate will be a business-savvy learning executive who understands the nuances of cloud services, the demands of client-facing teams, and the operational rigor required to support a high-growth organization. If this sounds like a good fit, we want to hear from you!

Requirements

• Bachelor’s degree in a related discipline and 10 years’ experience in a related field. The right candidate could also have a different combination, such as a master’s degree and 8 years’ experience; a Ph.D. and 5 years’ experience in a related field; or 14 years’ experience in a related field
• At least 10 years of experience in Learning & Development, with at least 5 years in a senior leadership role (Director+) within a technology or services organization.
• Proven success in designing and executing enterprise-wide learning strategies that drive measurable business outcomes, with the necessary financial acumen to clearly display the ROI of your organization.
• Expertise in instructional design, adult learning theory, and digital learning platforms.
• Strong executive presence and ability to influence across all levels of the organization.
• Experience managing cross-functional teams and vendor relationships.
• Background in change management, agile learning design, or operational excellence frameworks.
• Experience with sales enablement platforms, LMS systems, and performance analytics tools.

Nice To Haves

• Master’s degree in organizational development, education, business, or related field.
• Prior experience having founded a learning function, including execution of multiple learning roles simultaneously (e.g., trainer, instructional designer, leader)
• Deep understanding of cloud services, MSP business models, and the operational dynamics of Sales and Service Delivery teams.
• Familiarity with cloud platforms (e.g., Azure, AWS, Google Cloud) and related certifications.
• Certifications such as CPTD/APTD or equivalent.

Responsibilities

• Develop and execute a long-term learning strategy (minimum 3-year cycle) that aligns with business objectives, cloud service offerings, and operational excellence.
• Partner with executive leadership throughout the business to identify skill gaps, performance drivers, and growth opportunities.
• Serve as a strategic advisor to the COO and executive team on workforce capability and learning investments.
• Create and manage a trusted vendor ecosystem that provides access to scalable, role-based curricula for Sales (e.g., solution selling, cloud product knowledge) and Operations (e.g., service delivery, client onboarding), with other teams to follow.
• Oversee external instructional design teams to produce engaging, multimodal content including e-learning, virtual instructor-led training, and microlearning.
• Ensure learning programs consistently reflect the latest in cloud technologies, compliance standards, and customer-centric practices.
• Support citizen learning through thoughtful, accessible LMS administration, making department-specific modules widely available and providing coaching on efficacy.
• Build and manage a high-performing training delivery function that supports onboarding, upskilling, and certification across geographies in a full follow-the-sun model; the position will require occasional domestic and international travel to support our staffing partners.
• Implement metrics-driven training programs that improve time-to-productivity, reduce operational errors, and enhance customer experience; utilize those metrics to consistently show the value and return of your delivered work.
• Leverage a small team of internal SMEs with a variety of external vendors to deliver specialized training at scale while adhering to budget and timeline targets; establish clear rules of engagement for when to work with each delivery mechanism.
• Champion a culture of continuous learning, innovation, and operational excellence.
• Introduce governance models and learning analytics to measure impact, optimize resources, and inform future strategy, while consistently comparing performance of educational partners.
• Align learning initiatives with talent development, succession planning, and employee engagement efforts.

Benefits

• A competitive salary and top-notch bonus/incentive plans.
• Exceptional work-life balance, flexible time-off policies and accommodating work schedules.
• Comprehensive healthcare, with multiple options for individuals and families.
• Generous 401(k) retirement plans with up to 8% company match.
• Professional development and continuing education opportunities.
• Inclusive parental leave policies, plus comprehensive fertility coverage and adoption assistance.
• Extra perks like pet insurance, employee discounts and much more.
• The Company offers eligible employees the flexibility to take as much vacation with pay as they deem consistent with their duties, the company’s needs, and its obligations; seven paid holidays throughout the calendar year; and up to 160 hours of paid wellness annually for their own wellness or that of family members. Employees are also eligible for additional paid time off in the form of bereavement leave, time off to vote, jury duty leave, volunteer time off, military leave, and parental leave.
• Benefits of working at Cox may include health care insurance (medical, dental, vision), retirement planning (401(k)), and paid days off (sick leave, parental leave, flexible vacation/wellness days, and/or PTO).

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 501-1,000 employees