Leland
Direct Ashby career site

Retail & Merchandising Coach

Location
Remote (US)
Job type
Contract
Level
Senior
Listed
31 days ago

Skills & highlights for this role

  • retail strategy
  • merchandising strategy
  • inventory management

Also useful

  • sales forecasting
  • e-commerce integration
  • retail analytics

About Leland

Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously.

We're seeking an experienced retail and merchandising coach to work with students and professionals building careers in retail. This role includes teaching core skills in retail strategy, merchandising strategy, product assortment planning, visual merchandising, and pricing strategy, as well as inventory management, sales forecasting, supply chain management, and store operations.

Coaches also help students apply retail analytics, retail marketing, customer experience optimization, e-commerce integration, and AI fundamentals and automation to modern retail work. On the career side, coaches support resume review, cover letters, LinkedIn review, interview prep, and salary negotiation, as well as networking strategy and freelancing for those pursuing independent work.

Ideal candidates have professional experience in retail or merchandising, prior coaching or mentoring experience, and a clear, structured approach to breaking down strategic and operational retail concepts. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every student.

Why Leland?

  • The chance to join a world-class team helping people achieve their career and educational dreams
  • Work in a collaborative, high-energy environment where your contributions have a direct impact
  • Operate in a fast-paced, AI-native environment
  • We don't hire people who merely want to work for a great company; we hire people who want to make a great company
Read the original posting

From Leland's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

Rolev.ai is a job search and application tool for US job seekers. For this Retail & Merchandising Coach role at Leland, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.

  • See how you fit

    Openings from employer career sites are ranked against your whole resume—and searchable inside Claude, ChatGPT, and Cursor via Rolev.ai MCP.

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  • 1-Click Extension Autofill

    The Chrome extension fills the employer's Greenhouse, Workday, Lever, or Ashby form in 1 click. You review it and press Submit.

Common questions

Where is the Retail & Merchandising Coach job at Leland located?

Yes, this Retail & Merchandising Coach opening at Leland is listed as Remote (US). Always check Leland's application page for specific state eligibility or relocation policies.

What qualifications are required for Retail & Merchandising Coach at Leland?

For the Retail & Merchandising Coach role, Leland highlights experience with retail strategy, merchandising strategy, inventory management. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Retail & Merchandising Coach position at Leland?

This listing links directly to Leland's Ashby application page. You can apply directly on Leland's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.