Chief of Staff – Operations & Execution

About the role

iTelLe, a company combining advertising, BPO/contact center operations and tech-enabled growth, is looking for an autonomous, resourceful operator to work directly alongside its President / CEO as Chief of Staff – Operations & Execution. The role turns the CEO's big visions into concrete plans, coordinates work across departments and drives execution. It is based in the Dominican Republic (preferred) with a hybrid schedule overlapping US Eastern Time.

Key responsibilities

• Operational execution and strategic alignment (about 70%): turn executive concepts and priorities into roadmaps with owners, timelines and measurable goals.
• Coordinate with department leads in BPO operations, Marketing, Finance, HR and IT so deliverables are met without bottlenecks.
• Build and maintain dashboards and brief updates showing project health (green/yellow/red), roadblocks and decisions needed.
• Identify recurring friction points, draft Standard Operating Procedures (SOPs) and use AI and automation to cut manual work.
• Act as a sounding board, offering options, trade-offs and recommendations rather than open-ended questions.
• Executive and personal flow (about 30%): manage the CEO's schedule, meetings and follow-ups across time zones, and oversee personal appointments, travel and milestones with discretion.

Required profile

• Fluent professional English, written and spoken.
• Quick learner who takes ownership of projects from start to finish.
• Comfortable working with senior leaders, holding peers accountable respectfully and challenging assumptions with facts and data.
• Absolute integrity and reliability with sensitive executive and business information.

Required skills

• Understanding of systems and ability to use modern AI tools to speed up work.
• Adoption of new software intuitively; no deep programming knowledge required.

What we offer

• $2,200 - $2,600 USD per month as an independent contractor, plus performance bonuses and growth incentives.
• Closer access to the CEO and hands-on exposure to company-wide strategy and operational scaling.
• A flexible, high-trust environment focused on results, judgment and initiative.