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Chicago, IL - Sales Trainer

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Leaf Home
Full Time position
Listed on 2026-07-08
Job specializations:
  • Sales
    Sales Representative, Business Development, Sales Consultant, Sales Development Rep/SDR
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

Meet Leaf Home, the leading provider of technology-driven home solutions that is on a mission to make home ownership easy. With more than 50% of consumers worried about the cost and effort of home maintenance, we focus on delivering remarkable, end-to-end experiences. Trusted by more than 1 million homeowners across the US and Canada, Leaf Home is America’s largest direct-to-consumer full-service provider of branded home services and products.

Leaf Home and its products, including the patented Leaf Filter gutter protection system, have earned numerous awards and recognition from Good Housekeeping, Qualified Remodeler, Angi, Consumer Reports, This Old House, and other consumer review platforms.

Benefits

Industry-best compensation packages | Competitive health, dental, and vision insurance | 401k with company match | Paid Time Off including paid parental leave | Individualized career development programs | Childcare assistance | Employee assistance programs, including legal, financial planning, and counseling | Employee discount marketplace | Employee Resource Groups such as Vet Connect, DEI Committee, Women’s Committee

Apply today and together we will unlock millions of customers' dream homes and your dream career at Leaf Home.

Position Summary

The Sales Trainer is responsible for supporting all aspects of recruiting, onboarding, training, and development of Sales Representatives and Sales Consultants in the assigned market. This position will be responsible for one market with the opportunity to expand to multiple markets in the future where needed. The Sales Trainer works closely with Sales Operations Managers to meet or exceed established goals within the assigned market.

Focus areas include meeting or exceeding recruiting and onboarding of new sales personnel, revenue and sales targets, quality customer experience metrics, etc.

Essential Duties And Responsibilities
  • Participate in the development, implementation, and delivery of coaching and training plans that support the market and corporate goals and objectives utilizing the Company’s proven selling system.
  • Ensure Sales Representatives and Sales Consultants meet or exceed established sales and quality KPIs.
  • Support Sales Operations Managers with in-field training and development of Sales Representatives and Sales Consultants.
  • Help identify individual Sales Representative and Sales Consultant development opportunities, provide feedback and recommendations to Sales Operations Managers, and provide support towards closing identified developmental gaps.
  • Identify process deficiencies and inconsistencies and recommend improvements to support a unified and consistent sales process and customer experience.
  • Conduct in-person group training sessions with Sales Representatives and Sales Consultants on identified training opportunities.
  • Provide focused training on new technology platforms to improve efficiency, data integrity, and compliance.
  • Conduct ride-alongs with new and experienced Sales Representatives and Sales Consultants for quality assurance and training purposes.
  • When necessary, directly complete in-home sales demonstrations and provide sales quotes to customers.
  • Travel throughout the assigned market.
  • Performs other duties as assigned by supervisor.
Experience And

Minimum Qualifications
  • High school diploma or equivalent.
  • 2+ years of experience in direct selling, outside sales, or a related field.
  • 1+ years of experience in training and coaching outside sales representatives.
  • Ability to translate training documentation into real-world and practical applications.
  • Experience managing conflict resolution and motivating others to perform at a high level.
  • Ability to frequently travel within the assigned market.
  • Ability to juggle various work activities and shift their attention from one task to another to meet the demands of different stakeholders without “dropping the ball.”
  • Ability to thrive in a fast-paced, high-energy, team-oriented environment and have a “roll up your sleeves” and “win every day” mentality.
  • Hold oneself accountable and responsible while being self-driven in accomplishing goals.
  • Detail-oriented and can focus on task at hand by finding the most…
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