Director of Business Operations – E-Learning/Test Prep (Remote)

Seeking: Director of Business Operations — for Fast-Growing E-Learning Company

Chiefly connects top talent with innovative internet businesses. We’re excited to present this opportunity:

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Role Snapshot:

• Title: Director of Business Operations
• Position: #2 / Integrator (partnering directly with CEO)
• Compensation: $100,000 – $200,000 (USD)

Company Overview:

• Industry: Test Preparation (E-Learning / Ed-Tech)
• Stage: Fast-growing profitable bootstrapped startup
• Revenue: Multi-million $ (rapidly increasing)
• Team Size: 5 people
• Location: 100% Remote (US-based preferred)

Critical Requirement:

Small Company Experience is Essential

• You must have significant experience in small, fast-paced companies (ideally <20 employees)
• This role requires hands-on execution, not just strategy!

If your experience is primarily with 500+ person companies, this is unlikely to be a good fit (unless you joined during the early stages)

Why Apply:

• Work with visionary CEO (bestselling author & world-class tutor)
• Substantial autonomy in shaping team, operations, and strategy
• Drive impact in a high-growth, mission-driven ed-tech company

Challenges You’ll Face:

• Your performance will be highly visible – directly impacting the company’s success
• High-pressure environment, fast-paced
• Self-direction & comfort with uncertainty
• Building business systems from scratch
• Fast-paced learning environment

Requirements

What We’re Looking For:

Experience:

• 5+ years in online business (ed-tech, info-products, or e-learning preferred)
• Proven track record scaling operations and managing teams
• Strong business acumen: OKRs, budgets, metrics, vendor management

Skills:

• Intelligent, extremely fast learner
• Proactive problem-solver who takes massive action
• Exceptional communication with transparent candidness

Mindset:

• Balance of hunger, scrappiness, and strategic thinking
• Comfort with ambiguity and ground-up building

Key Responsibilities:

• Free up CEO’s time and focus
• Build and manage a growing team
• Oversee business operations and financials
• Support ambitious growth targets

Reporting:

• You’ll report directly to the CEO.

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Is this you?

Don’t just apply – convince us you’re the leader we need.

Apply here and show us why you’re the perfect fit!

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Brought to you by Chiefly – connecting elite executive operators with high-performing internet businesses.