Free The Sheep | Part-Time | Independent Contractor (1099) | Remote

About Free The Sheep

Free The Sheep is a fast-growing e-commerce comfort and lifestyle brand focused on creating products people love to wear, use, and experience.

Our flagship product, the Eden Hoodie™, has become a cornerstone of our business. We're now looking to expand our product assortment, introduce exciting new colors, patterns, and limited-edition collections, and develop entirely new products that increase customer loyalty, repeat purchases, and lifetime value.

We're looking for a creative, commercially minded, and highly hands-on Fractional Head of Product Design & Development who can help lead the next chapter of our product evolution.

This is not a traditional corporate leadership role. We're a fast-moving entrepreneurial company, and we need someone who can both develop the product strategy and execute the day-to-day work required to bring products to market.

The Role

You will own and help execute our product design and development roadmap, from identifying new opportunities and creating designs to coordinating tech packs, supplier sampling, revisions, and launch readiness.

You'll work closely with our founders, operations team, external technical design contractors, and manufacturing partners to turn ideas into commercially successful products.

Our ideal candidate understands that great product design is not just about aesthetics. It's about creating products customers want to buy, collect, gift, and come back to purchase again.

Key Responsibilities

1. Expand and Improve Our Existing Product Line

Analyze our best-selling products, customer preferences, reviews, sales data, and market trends.
Develop new variations of existing products, particularly our Eden Hoodie and related comfort products.
Create new colorways, patterns, prints, textures, and seasonal designs.
Identify opportunities for limited-edition collections, themed drops, and holiday releases.
Explore variations in materials, functionality, fit, construction, and product features.
Balance creativity with commercial potential, manufacturing feasibility, and profitability.

2. Lead New Product Development

Research and propose new product categories that complement our existing assortment.
Identify opportunities to increase repeat purchases, average order value, and customer lifetime value.
Explore adjacent categories such as comfort apparel, loungewear, blankets, bedding, accessories, and other lifestyle products.
Develop concepts, mood boards, sketches, designs, and product specifications.
Prioritize product opportunities based on customer demand, brand fit, expected profitability, and speed to market.
Turn approved concepts into actionable development projects.

3. Research Competitors and Market Opportunities

Continuously study successful brands in comfort apparel, lifestyle products, bedding, and adjacent categories.
Identify winning products, popular design trends, emerging categories, and product differentiation opportunities.
Analyze competitor pricing, launches, product drops, customer feedback, and merchandising strategies.
Identify gaps in our assortment and opportunities to introduce products that drive additional purchases.
Present actionable recommendations rather than simply compiling research.

4. Own Prints, Patterns, and Creative Product Design

Develop original prints, patterns, graphics, and product design concepts.
Design seasonal, thematic, and trend-driven collections.
Explore opportunities for collectible product drops and coordinated product families.
Collaborate with the team on potential licensed collections and partner-driven designs.
Ensure every design feels consistent with the Free The Sheep brand while introducing fresh ideas.
Prepare clear design files and specifications suitable for production.

5. Manage Tech Packs and Supplier Development

Work closely with our existing technical design contractor to create and finalize production-ready tech packs.
Communicate directly with suppliers and manufacturers to translate designs into physical products.
Coordinate sample requests, material selections, print techniques, specifications, and revisions.
Review product feasibility, costs, quality expectations, and production requirements.
Ensure suppliers have everything necessary to begin sampling quickly.

6. Drive Fast Sampling and Product Iteration

Own the sample development process from initial request to final approved sample.
Proactively follow up with suppliers to minimize sampling delays.
Review samples for quality, fit, feel, functionality, construction, and design accuracy.
Organize feedback and communicate clear revisions to manufacturers.
Coordinate multiple rounds of sampling when needed, with a strong focus on reducing turnaround times.
Maintain visibility into every product's development status, outstanding revisions, and expected delivery dates.

7. Own the Product Development Pipeline and Launch Calendar

Build and maintain a centralized product development tracker.
Keep track of concepts, designs, tech packs, suppliers, sampling rounds, approvals, costs, and production readiness.
Collaborate with our founders, marketing team, and operations team on a rolling product launch and drop calendar.
Plan product releases around holidays, seasonal demand, marketing opportunities, and inventory timelines.
Identify bottlenecks early and keep development projects moving.
Provide regular, concise updates on what's being developed, what's delayed, and what's ready to launch.

8. Help Build a Product-Led Repeat Purchase Strategy

Think beyond one-time purchases and help build reasons for customers to return.
Develop new complementary products, matching collections, seasonal colorways, and limited-edition releases.
Identify opportunities for bundles, gifting, product extensions, and collectible designs.
Use customer feedback and sales performance to determine which products and variations deserve further investment.
Collaborate with the marketing team to develop product concepts that are visually compelling and easy to market.

Who We're Looking For

5+ years of relevant experience in consumer product design, apparel, textiles, accessories, home goods, or product development.
Experience taking physical consumer products from concept through sampling and production.
Strong creative design skills, particularly in prints, patterns, colorways, and product variations.
Experience working directly with overseas manufacturers and suppliers.
Familiarity with tech packs, textiles, materials, manufacturing processes, and sample development.
Ability to manage multiple product development projects simultaneously.
Strong commercial instincts and an understanding of what drives consumer purchasing behavior.
Familiarity with direct-to-consumer brands, e-commerce trends, and product launch strategies.
Proficiency in relevant design software such as Adobe Illustrator, Photoshop, or comparable tools.
Excellent organization, follow-through, and communication skills.

Most importantly, you must be an executor. We are not looking for someone who only builds strategy decks, manages agencies, or delegates work. We need someone comfortable designing products, communicating with factories, chasing samples, reviewing revisions, and keeping projects organized.

Bonus Qualifications

Experience designing hoodies, fleece products, oversized apparel, blankets, bedding, or comfort-oriented consumer products.
Experience developing licensed merchandise, character-inspired collections, or limited-edition collaborations.
Experience with high-growth Shopify or DTC brands.
Strong understanding of customer retention and product assortment strategy.
Existing relationships with reliable apparel, textile, or home goods manufacturers.
Experience building seasonal collection calendars and limited-edition product drops.

Engagement Details

Type: Part-time, fractional independent contractor (1099).
Location: Remote.
Hours: Approximately 15–25 hours per week, with flexibility based on development cycles.
Compensation: Competitive, based on experience and scope.
Team structure: Hands-on individual contributor working directly with founders, contractors, suppliers, and operations. No dedicated team to manage.
Opportunity: Potential to expand the engagement as the business and product assortment grow.

What Success Looks Like

Within your first 90 days, we'd like you to:

Complete an audit of our existing products, customer feedback, and competitor landscape.
Present a prioritized roadmap of new product opportunities and extensions of existing products.

Free the Sheep jobs

Fractional Head of Product Design & Development