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How to Hire the 5 Ecommerce Roles That Will Make or Break Your Brand

OPERATORS · May 20, 2026 · 67 min

Summary

Hiring top-tier talent in ecommerce is notoriously challenging, and this episode dives into the five roles that can truly make or break an ecommerce brand: Head of Product, Head of Growth, Head of Amazon, Creative Strategist, and Head of Influencer. The discussion challenges conventional wisdom, asserting that while Head of Growth is commonly perceived as the hardest, a visionary Head of Product is often the most critical and difficult to replace, especially for long-term brand expansion and innovation. Ecommerce operators will gain insights into the strategic importance of these roles and the nuanced skills required for each.

Key takeaways

Themes

founder & leadershipproduct & merchandisingsupply chain & operationsai & automation

Topics covered

ecommerce hiringhead of producthead of growthhead of amazoncreative strategisthead of influencerorganizational structureai in supply chainproduct development strategy

Episode description

“The right person does nothing but print money.” Sean Frank, Matt Bertulli, Curtis Matsko, and Katy Mimari get into a heated debate on the hardest roles to hire in ecommerce. Nobody agrees. And that’s exactly the point. The conversation tears through five make-or-break positions: (1) head of product, (2) head of growth, (3) head of Amazon, (4) creative strategist, and (5) head of influencer. Along the way, they expose why CMO is the shortest-tenured C-suite role for a reason, how a wedding photographer became a top-performing CMO, and what it takes to lock down great talent before they go build something on their own. Powered ByFulfilhttps://9ops.co/fulfil Saras Analyticshttps://bit.ly/9OP-Ytdesc Postscripthttps://9ops.co/postscript Richpanelhttps://9ops.co/richpanel Northbeamhttps://www.northbeam.io/ Aftersellhttps://9ops.co/4i3bb5 Operators Newsletterhttps://9operators.com/

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Frequently asked about this episode

What does this episode say about founder & leadership?
A visionary Head of Product is arguably the most challenging and crucial hire, as their absence can severely stifle innovation and growth, transcending typical product development to strategic category expansion.
What does this episode say about product & merchandising?
Don't underestimate the difficulty of hiring for roles that require a blend of creative vision, strategic execution, and market understanding, such as Creative Strategist and Head of Influencer.
What does this episode say about supply chain & operations?
The definition of 'hard to hire' can be category-specific; brands with inherent expansion opportunities (e.g., baby products to toddler) might find product roles easier, while those in saturated or niche markets face greater challenges.
What does this episode say about ai & automation?
For scaling brands, consider restructuring your organization to elevate product development to an equal tier with marketing and operations, allowing for more strategic focus and avoiding it being solely a marketing function.
What does this episode say about founder & leadership?
Leverage AI tools, such as Claude with Fulfill, for supply chain optimization and custom dashboard creation to free up your team for more strategic, high-value tasks.

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