Director of Training

Job Summary
The Director of Training will lead the strategy, design, and execution of training programs across a large, multi location retail organization with 230 locations nationwide. This role is responsible for the full lifecycle of training, supporting frontline sales professionals, high potential leaders, and future General Managers, as well as owning training readiness for new location openings.
This leader must come from a retail industry background, bringing hands on experience training customer facing teams in fast paced, performance driven environments. Experience within automotive retail is a significant plus. The ideal candidate is an innovative, self starting leader who brings fresh ideas to learning and development, including the use of modern tools and emerging technologies such as AI to scale and enhance training effectiveness.Key Responsibilities
• Lead, mentor, and develop a team of 5 direct reports (4 Trainers and 1 Instructional Designer).
• Own and execute the end to end training lifecycle, including needs analysis, curriculum design, delivery, evaluation, and continuous improvement.
• Design and deliver training programs for:
o Sales professionals
o High potential leaders and future General Managers
o Dealership and retail location leadership teams
• Lead training strategy and execution for new location openings, including:
o Coordinating closely with Recruiting on hiring timelines
o Ensuring training readiness aligned with launch schedules
• Partner with HR, Recruiting, and Operations to ensure training supports workforce planning and business growth.
• Drive innovation in training methodologies, content, and delivery models.
• Identify and implement opportunities to leverage AI, digital learning platforms, and blended learning approaches.
• Travel up to 50% to support field locations, leadership teams, and new market launches.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to View email address on click.appcast.io learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy:


Required Skills & Experience
• Retail industry background is required, with experience supporting customer facing, sales driven teams.
• 10+ years of relevant experience in training, learning & development, or talent development within a retail environment.
• Proven people leadership experience managing trainers and instructional design resources.
• Experience delivering training across multi site or field based retail organizations.
• Demonstrated ability to own programs from concept through execution at scale.
• Strong cross functional partnership skills with HR, Recruiting, and Operations.
• Self starter with the ability to operate independently and drive results.
• Willingness and ability to travel approximately 50%.


Nice to Have Skills & Experience

Preferred Skills & Experience
• Automotive retail experience (dealership, OEM retail operations, or similar) is a strong plus.
• Experience developing training programs for sales organizations and leadership pipelines.
• Experience supporting new store, dealership, or market openings.
• Innovative mindset with experience or strong interest in:
o AI enabled learning tools
o Learning Management Systems (LMS)
o Digital, virtual, and blended learning strategies
• Experience designing scalable training solutions for large, geographically dispersed retail organizations.


Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.