Origin Stories

For decades, the industry has developed talent organically in stores, distribution centers, training programs, rotational programs and internships. These experiences exposed employees to the mechanics of retail firsthand, putting them in close proximity to customers and management. Many of today’s most recognized retail leaders began their careers in those environments.

The stories of hero journeys to the top are retail lore. Think of Mike Gould, former Bloomingdale’s CEO, and Mark Cohen, TRR’s contributor and former CEO of multiple retail brands, who got their start at the now-legendary Abraham & Straus Executive Training Program. The dedication, loyalty, and ground-level expertise shaped by good training programs are praised as keys to unlock grooming future CEOs and shepherding them into an organization’s future. For investors, executive training signals leadership which has intimate knowledge of the inner workings of their organizations. For emerging leaders, it can paint the picture of a future Cinderella story, from the ground floor to the corporate suite.

Retail has historically developed leaders from within, for better or worse. In 2026, however, the pathway these merchant princes are taking looks entirely different. Entry-level jobs continue to be a revolving door, if retail can even attract next gens to the profession. The roles of the store and the store associate do not appear to be popular career choices for young graduates. Megabrand tech companies are the siren calls of many well-educated next gens, despite the fact that retail tech has opened opportunities for a host of young workers looking for tech-based careers.

Combined, these forces are creating an uncertain future for the pipeline of talent to produce retail’s next generation of leadership. The graduating class of 2026 will be met with a job market that is smaller, more automated, and structurally different than the one that produced current retail leaders. Why isn’t retail considered a viable career option for next gens? Why is it perceived as a dead-end for sales associates, a temporary way station? Or to be blunt, why is retail so far behind in making itself an attractive, fulfilling career?

Internship and Mentoring

Historically, internships have been the preliminary exposure point and starting rung for many college students looking to enter the retail and fashion industries. Hiring rates have taken a steep decline in past years. As a positive sign, however, the National Association of Colleges and Employers (NACE) expects employers to increase hiring of interns by nearly 4 percent this year.

Despite the projected increase in internship opportunities, conversion rates into full-time employment are difficult to assess due to the lack of transparency. Free or very low-cost labor doesn’t sit well with ambitious Gen Zs. Add to that, internships in an industry hub like New York, Los Angeles, or Paris come with substantial housing and living expenses. Internships as the main trajectory for identifying future retail leaders have become a fool’s errand for many young hopefuls.

Mentoring, particularly reverse mentoring, is an effective strategy to develop future leaders. Whether mentorship programs are established within retail organizations or coached externally, they are effective at bridging theory to practice. Mentoro is a non-profit focused on mentorship and career development within the fashion and retail industries. Programs like this reflect a growing recognition that career advancement often depends as much on access, exposure, and professional networks as it does on technical capability. The Robin Report’s own Lead Like Her series was created to help elevate honest conversations around leadership and provide visibility into career journeys across the industry with successful models for future leaders.

Climbing the AI Career Ladder

In the next few weeks, a fresh batch of hopefuls will be entering the workforce. Admittedly, the job market today is not the same as it was for past generations. Headlines report a miserable job market, and for retail in particular, it has contracted. Although April jobs data showed a surge in hiring in the retail sector, retail employment is still down, and 2025 experienced the largest rate of overall job cuts since 2020. The retail industry was among the hardest hit, with 92,989 job cuts announced, an increase of 123 percent from the prior year. These cuts are not limited to the sales floor; technology is driving a significant refocus of talent at the management level.

Electronic Shelf Labels (ESLs), self-checkout systems, robotic fulfillment centers, computer vision, and other AI applications are reshaping roles in retail. In some experiments, AI has been used to fully run retail locations ranging from a vending machine to an entire boutique store. Although these models are novel and science fiction-esque, the projections are not. The Bureau of Labor Statistics (BLS) projects that cashiers will have the largest occupational job decline in the coming decade, with a projected loss of over 300,000 jobs. Also on that list of high occupational declines are front-line retail supervisors and retail salespeople.

This poses an existential crisis for retail. Do sales associates have a place in the tech-fueled store of the future? And if entry-level retail jobs disappear and the bottom rungs of the corporate ladder are removed, what will be the entry point for future talent to start climbing? For the college student looking to get started on their ascent this summer, their entry-level prospects have never been more competitive.

Some retailers are strengthening their leadership ladders. These retail programs follow different philosophies and each updates traditional systems.

• URBN’s Made to Measure Merchant Leadership program is an immersive accelerator for early-stage career merchants. Its Apprenticeship program is run in partnership with Drexel University. It is a two-year program that covers full tuition, room and board, and pairs coursework with rotations across URBN brands, and an employment offer at the end of the program. Additionally, URBN offers a variety of tracks and development programs for its employees, including a Store-to-Home-Office
• Macy’s Store Management Executive Development Program is a two-year rotational assignment. This structure applies the “four-wall” philosophy of business; effective management requires an ability to understand sales, customer experience, visual merchandising, logistics, and business administration.
• Walmart has evolved heavily over the past few years and now offers one of the most notable incentive structures in the industry. An increased minimum wage, store manager bonus packages, and tuition assistance programs are offered by the largest employer in the U.S. The retailer employs 2.1 million associates worldwide, with 1.6 million in the U.S., deomnstrating that programs can work at scale.

Filling The Gap

Although a few retailers are working to build a viable leadership pipeline, these cases are few and far between. Even within organizations that have established internship programs, tuition initiatives, or rotational tracks, the broader industry still faces a retention problem. In a shrinking job market, the roles that remain are plagued by a high churn rate. The retail industry has the second-highest quit rate of any major industry sector at 2.7 percent. Replacing these employees comes at a steep cost, up to $10,000 per employee.

The churn rate reveals a systemic problem in cultivating the next generation of retail leaders. Next gen employees are redefining workplace expectations and goals. TRR recently reported on Gen Z bosses who are ironically unbossing themselves. Next gen employees have unabashedly reset the rules of retail management. Aside from resisting leadership roles, the traditional career ladder was never the goal for many next gen workers. Portfolio careers, a mix of part-time roles, freelance work, side projects, and selective full-time commitments, have become a deliberate choice rather than a fallback. In fact, 64 percent of American Gen Zs believe having multiple revenue streams is essential for financial security, called “income stacking.”

When workers’ interests spread across roles, where does their focus lie? This is particularly challenging for an industry with a high retention problem. Even with established pipelines, workers may not want to stay long enough to climb them. It also highlights a mismatch between what the industry is offering, and what the next generation is optimizing for. One of the biggest risks of the high churn rate is how to protect and preserve institutional knowledge. Retail leaders are challenged with archiving legacy knowledge that can serve as living, relevant histories, best practices, and playbooks.

The Legacy Rewrite

Here are some alarming stats:

• Retail has the second-highest quit rate of any major industry.
• A 0% recommendation rate on a flagship development program.
• 93,000 announced job cuts in 2025.

These are the results of a system that does not adapt and has stopped cultivating talent. Whether retail can reverse this is unclear, which may only give way to more tech optimization and retail becoming less human. Add to that, the technology reshaping the store is moving faster than the talent systems can respond to it. If that gap widens, the store of the future may have fewer people in it, both customers and employees, not more capable ones. The next generation of workers is redefining what a career looks like, and the industry is still largely following a talent development story with a pipeline strategy built 40 years ago. At some point, soon, the story and the system need to be rewritten.