Director of Training, Retail

  • New York, Chicago, or L.A., NY
  • Full Time
  • Retail Operations
  • Senior Manager/Supervisor

About Leap

Leap is building the world's largest network of branded retail stores – powered by data, systems and scale.  The Leap Platform enables brands to deploy stores that work in concert with e-commerce more rapidly and at significantly reduced cost and risk.  Brand stores powered by Leap bring modern brands to life with compelling, immersive customer experience and data driven operations.  At Leap, our diverse, growing team is excited by the opportunity to power the next generation of leading consumer brands with a vibrant presence in local communities throughout the country.  We're one of the fastest growing companies in the retail/e-commerce space - since launch we've powered stores for dozens of brands, and we're adding more brands and stores each week.


Our brand customers are modern brands who lead or aspire to lead their categories today and tomorrow, and *outstanding* people are literally at the core of our product.  Our organization is composed of a diverse range of talented individuals and teams.  With functions like Real Estate, Store Design & Development, Retail Operations, Marketing, Engineering, Product Management and Data Science, we are truly a unique company and our shared ambitions and core values tightly align and drive us to succeed. 

Our staff are what make our organization so special and honoring our culture and values as we hire, onboard, engage, develop and support our teams is paramount.

Come take this leap with us. Your ideas, thinking, and voice are wanted.


The Role

The Head of / Director of Training, Retail will be responsible for the design, development and facilitation of a training curriculum for all Leap retail employees. The fundamental charter for the role is the design and delivery of training strategy and the creation of key programs to enable both individual and organizational growth through transformation, leadership and selling skills, as well as managing and motivating a world-class team.


This role will be charged with the development of people, processes and systems to support Leap’s continued rapid growth. This individual will have overall responsibility for iterating on and executing a cohesive training strategy to drive sales, employee engagement and performance. This role will drive learning initiatives through digital tools and will oversee the Learning Management System (LMS). 


This role is a unique opportunity to develop training and success for over 25 brands on the Leap platform such as Naadam, Something Navy, ThirdLove, Birdies, Mack Weldon and more. Ideally, this role will be based out of one of our corporate hubs: Chicago, Los Angeles or New York.


Key Responsibilities:

  • Lead the ideation and development of strategic programs and training paths relevant to Leap, brands and roles
  • Design, develop, organize and facilitate training in an engaging and informative manner including but not limited to: new store opening training, on-boarding programs, product knowledge, selling skills, customer service and other soft skills based on identified performance gaps
  • Work closely with the leadership team to determine training needs in alignment with short, medium, and long-term business priorities and initiatives
  • Partner with internal stakeholders to evaluate training opportunities across brands and departments and execute learning and development plans 
  • Deliver qualitative post-training analysis in terms of customer experience, impact on sales and loyalty growth
  • Research, propose and test training solutions to drive operational efficiencies and increase sales
  • Manage the deployment of both in-person and e-learning curriculum and measure progress, results and compliance through KPIs, reports, and evaluations
  • Monitor the impact of retail training through regular store visits and deliver in-store coaching to enhance performance
  • Oversee the continued use and development of the Learning Management System (LMS)
  • Attract, hire, train, inspire and retain a high performing training team who are focused on developing best-in-class training across multiple audiences


Qualifications – key competencies & attributes for success:

  • 10+ year of training experience with a track record of success
  • Outstanding sales and service skills, specifically in a luxury environment
  • Interest in identifying, mapping and modeling new training opportunities – including growth across new brand categories, product lines and partnership models
  • Knowledge of developing and delivering training solutions –  including instructional design, storytelling and facilitation 
  • Strong communication skills, both at verbal and written level with audiences of different seniority and varying backgrounds
  • Strong leadership skills developed via managing people and teams
  • Ability to think and work strategically; can problem solve; looks at obstacles as opportunities; goes the extra mile; has a passion for scaling a company; and a desire to develop “A” players within their team
  • Advanced knowledge of retail fundamentals such as retail calendars, sales/traffic dynamics and the basics of retail operations
  • Entrepreneurial mindset and working style - self-starting, highly accountable, ability to anticipate problems and define and implement effective solutions, desire to win
  • Exceptional attention to detail and ability to operate “in the weeds” while maintaining sight of the big picture


Outcomes & measures of success:

  • Increase in sales across Leap platform driven by an enhanced in-store experience
  • Successful cross-functional collaboration with peers and others throughout the organization
  • Hire and develop a strong, high performing team 
  • Successful development, implementation and rollout of new training and sales programs in partnerships with relevant stakeholders
  • Operationally efficient and compliant stores based on standard operating procedures


However you identify, whatever your path to get here; Leap celebrates diversity and is committed to maintaining a safe, rewarding and inclusive environment where Leapers thrive individually and as a team.  In order to achieve our mission, building the world's largest network of branded retail stores – powered by data, systems and scale; we need to work hard to foster a diverse community to support the brands and customers we serve. These aren't just words, this is who we are. We know that our differences are what make our organization special and are paramount to our culture. Your age, skin color, beliefs, sexual orientation, nationality, disability, parental status, vet status, gender identity are valued.



Read More

Apply for this position

Apply with
We've received your resume. Click here to update it.
Attach resume as .pdf, .doc, .docx, .odt, .txt, or .rtf (limit 5MB) or Paste resume

Paste your resume here or Attach resume file

To comply with government Equal Employment Opportunity and/or Affirmative Action reporting regulations, we are requesting (but NOT requiring) that you enter this personal data. This information will not be used in connection with any employment decisions, and will be used solely as permitted by state and federal law. Your voluntary cooperation would be appreciated. Learn more.