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Fractional CMO (Retail) — Build & Own a High-Performance Marketing Engine - Contract to Hire

June 29, 2026

Description If you’ve never built a marketing machine from zero to scale in a competitive retail environment, this is not for you. We are building Directly.io — and we are looking for a true operator, not a consultant. Directly.io is a next-generation supply chain platform designed to replace the traditional distributor model by giving brands direct access to a fully integrated, end-to-end retail ecosystem in the U.S. market. Combining infrastructure, AI-powered operations, and embedded execution teams, it enables brands to seamlessly enter, operate, and scale across retail and e-commerce without relying on fragmented intermediaries. Someone who has already done it. Someone who knows exactly what to build, in what order, and how to execute without friction. ⸻ The Opportunity This is a high-leverage, strategic role with direct impact on the trajectory of the company. You will not be “advising.” You will be designing, building, and owning the entire marketing system. From positioning to acquisition, from structure to execution — you are responsible for making it work. ⸻ Scope of Work You will lead and execute across • Positioning & Brand Architecture Craft a clear, differentiated market position that converts • Acquisition Strategy & Execution Paid, organic, partnerships — designed for scale and efficiency • Growth Systems & Funnels Build a coherent, high-performance acquisition engine • Marketing Operations Tracking, attribution, tooling, performance visibility • Go-To-Market Execution From strategy to deployment — fast, structured, measurable ⸻ Non-Negotiable Retail Expertise You must have deep, hands-on experience in retail. We are not interested in adjacent experience. You understand • DTC and/or marketplace dynamics • Product-driven growth and conversion mechanics • Customer behavior in competitive retail environments • Scaling acquisition with real budget constraints and performance pressure If this is not your background, do not apply. ⸻ Profile We’re Looking For • Former or current CMO / Head of Marketing / Senior Growth Operator • Proven track record of building and scaling marketing systems • Strong execution capacity (not just strategic thinking) • Comfortable operating in high-expectation, fast-paced environments • Ability to own results end-to-end ⸻ This Is Not For You If • You are purely strategic and don’t execute • You rely on teams to “figure it out” • You’ve only worked in low-performance or slow environments • You cannot clearly demonstrate past results ⸻ Application Requirements (Strict) We only review high-quality, substantiated applications. Include 1. Concrete case studies → What you built, how you built it, and the measurable results 2. Retail experience breakdown → Companies, role, scale, channels managed 3. Your operating approach → If you had to build a marketing system from scratch today, what are your first 3 moves and why? 4. Proof of execution → Metrics, dashboards, examples, or anything tangible Apply To this Job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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