Fractional Director of Operations (AI-First OS) → COO Track (Remote)
- $60k – $90k • No equity
- |Remote (Canada •+2)
- |5 years of exp
- |Contract
Remote only
Not Available
About the job
Company: Cocoon
Stage: $1.7M+ revenue (2025) | Scaling to $2.5M+
Location: Remote (LATAM or US time zones)
Commitment: 15–25 hrs/week | 4–6 months | Potential full-time COO path
About Cocoon
Cocoon is an AI-first curated marketplace connecting design-led spaces with the creative industries (fashion, production, art, corporate).
We are finalizing Stage 1 of the business and preparing to scale to new cities.
Our broader mission:
We believe design, architecture, and art should be accessible to everyone. Cocoon is building the operational infrastructure that will eventually support social architecture initiatives expanding access to extraordinary cultural environments.
The Role
We are hiring a senior operations leader to architect and implement our AI-first operating system.
This is a hands-on builder role combining:
- Systems architecture
- Automation
- Financial rigor
- Multi-team leadership
- This is not a consulting engagement.
What You’ll Own
- Architect and implement our AI-first OS
- Automate CRM → bookings → logistics → finance workflows
- Streamline bookings operations (sales + logistics) for speed and margin
- Build structured concierge and vendor databases
- Install KPI dashboards across departments
- Lead 2026 budgeting and forecasting
- Oversee day-to-day operations during transition
- Reduce dependency on clerical finance work through smart systems
Ideal Profile
- 5+ years in startup or marketplace operations leadership
- Strong automation stack (Make/n8n/Relay + Notion/ClickUp + CRM)
- AI workflow integration experience
- Financial modeling & KPI fluency
- Proven experience managing multi-functional teams
- Comfortable leading team leads
- Calm, structured, execution-oriented
- Proficient, business-level English (written & spoken)
Why This Role Matters
- You will design the operational backbone that enables Cocoon to:
- Scale geographically
- Increase margins
- Reduce founder bottlenecks
- Professionalize infrastructure
- Transition toward long-term executive leadership
- This role has a clear path to evolve into COO.
To Apply
- Please include:
- The most complex system/automation you’ve built (tools + measurable impact)
- Weekly availability (hrs/week)
- Expected monthly compensation
- Location / time zone
We are looking for a serious builder who wants to architect infrastructure at scale.
About the company
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