Sales Trainer

Sales/B2B Dodgeville, Wisconsin

Lands’ End® is a classic American lifestyle brand with a passion for quality, legendary service, real value and a simple two-word promise to stand behind everything it sells: Guaranteed. Period.® Lands’ End delivers timeless style for Men, Women, Kids and the Home. With over 50 years of experience, Lands’ End is renowned for its culture of service for the customer and is recognized as an innovator in the industry. Lands’ End is publicly traded and listed on NASDAQ under the trading symbol (LE).

Lands' End Business Outfitters is a trusted brand partner for companies of all sizes, offering businesses a better choice through quality, high-value apparel and promotional products. From single entrepreneurs to members of the Fortune 500®, Lands' End Business Outfitters offers tailored and business casual apparel for office wear, trade shows, company events and more. Lands' End Business Outfitters also offers an extensive variety of promotional products that enhance a company's image and message.

As the Business Outfitters Lands’ End Sales Enablement Specialist, you will develop and present sales training programs for all areas of the Outfitters business to support the overall business development and retention goals. You will implement tools and training to further enable us to develop a world class sales organization. You will also work in collaboration with our sales leaders to develop sales tools and guidelines to support the process across the Outfitters division and ensuring those are being utilized to the fullest in each area of the division.

 Key Responsibilities:

  • Deliver sales training to all segments of the Outfitters business groups including sales managers, inside and outside sales teams and inbound Outfitters consultants.
  • Plan, coordinate and deliver new hire training and partner with other supporting areas to help onboard and ramp new field sales representatives. Travel in field to conduct training- 10%.
  • Identify learning objectives based on Outfitters business objectives, review current content and develop new course content, teaching methods, and instructional procedures for sales training. Continuously evaluate progress and results to ensure sales training activities continuously evolve and develop.
  • Assist in LMS and E-learning- identify and create content for online training.
  • Identify external sources for complimentary training content to enhance existing training materials.
  • Maintain continual awareness of business strategy and objectives; recommend sales training techniques and approaches to Outfitters management to assist in meeting sales goals.
  • Develop and enhance tools and guidelines to support the sales process.
  • Develop and execute a monthly sales coaching plan with collaboration of the Outfitters sales managers.
  • Identify, measure, and communicate progress against overall sales metrics for the division.
  • Ensure compliance of the sales process across all areas of the organization and measurement of compliance.


Successful candidates should have the following knowledge, skills and abilities:

  • Minimum 4 years sales training experience preferred
  • Field Sales experience preferred but not mandatory
  • Excellent interpersonal and communication skills, both verbal and written.
  • Ability to think strategically and drill down in to the details
  • Demonstrated project management skills as well as strong analytical and problem-solving abilities
  • Extensive experience in designing educational methodology and creating a learning environment for adult learners
  • Knowledge and understanding of Lands’ End culture
  • Ability to learn material quickly, turn around and train others ensuring all material is consistent with LE culture and values
  • Capable of working in a fast-paced ever changing environment and ability to coordinate multiple projects simultaneously
  • Proficient in developing and leading change management methodologies and techniques as well as communication management techniques and processes
  • Proven organizational skills
  • Flexible and able to adapt and lead others through change with a positive attitude
  • Ability to identify opportunities for process improvement
  • Systems savvy; Proficient in PC and Microsoft applications
  • Bachelors degree in related area (Business Management, Human Resources, Supervisory Management) or equivalent experience strongly preferred.
  • Ability to travel- approximately 10%