Operations Lead & Executive Assistant (Chief of Staff Track)

About the job
Operations Lead & Executive Assistant — Chief of Staff Track

Compensation

South Africa: $2,500 – $3,000 USD/month
Colombia / Argentina: $2,000 – $2,700 USD/month

Location: Remote, South Africa, Colombia, or Argentina

Schedule: Full-time, aligned with U.S. Pacific Time (PT)

Employment Type: Full-Time Independent Contractor

Reports To: Founder & Fractional CFO

About The Company

Our client is a growing fractional CFO advisory firm serving approximately 30 startup and growth-stage clients, from early-stage companies through Series A and Series B.

The founder operates the advisory firm alongside a senior executive role in the entertainment industry. As the business continues to grow, he is looking for a highly capable operational partner who can bring structure, organization, and leverage to the company.

This is an opportunity to join a growing business at an early stage and develop into a long-term leadership position.

Role Overview

The Operations Lead & Executive Assistant will serve as a trusted operational partner to the Founder & Fractional CFO.

The role will initially focus on executive support, inbox and calendar management, client follow-up, documentation, and keeping day-to-day priorities organized. As the candidate develops a strong understanding of the business, the position will expand into broader operations, process improvement, CRM management, client experience, business development, and strategic project execution.

This is not a traditional Executive Assistant position.

The ideal candidate is highly proactive, organized, commercially aware, and capable of taking an outcome and independently figuring out how to make it happen.

The long-term goal is for this person to grow into a Chief of Staff role, becoming the founder’s operational right hand and taking increasing ownership of the firm’s day-to-day operations.

Key Responsibilities

Executive Support

Own and organize the founder’s inbox, including prioritization, follow-up, and professional correspondence
Manage the founder’s calendar across multiple priorities
Protect focus time and proactively resolve scheduling conflicts
Prepare the founder for meetings by organizing relevant information, action items, and follow-ups
Maintain visibility across priorities, deadlines, and outstanding commitments
Proactively identify loose ends and ensure they are closed

Client Operations

Coordinate follow-up with the firm’s approximately 30 clients
Track outstanding client requests, financial documents, statements, and reports
Follow up with clients to ensure requested documentation is received
Help coordinate client onboarding and ongoing client communication
Maintain organized client records and workflows
Identify bottlenecks and escalate issues requiring the founder’s attention
Help ensure clients receive timely, professional communication

Business Operations

Learn the firm’s existing workflows and identify opportunities to improve efficiency
Build and maintain repeatable processes and Standard Operating Procedures (SOPs)
Create systems that reduce manual follow-up and prevent tasks from falling through the cracks
Take ownership of operational projects from concept through completion
Improve organization, accountability, and visibility across the business
Identify opportunities for automation, delegation, and process improvement

CRM & Growth Support

Maintain and organize the company’s CRM
Keep client information, contacts, statuses, opportunities, and follow-ups current
Track prospective clients and business development activity
Support outreach to prospective customers
Coordinate marketing and business development initiatives
Schedule discovery calls and maintain prospect follow-up
Help maintain visibility into the company’s sales pipeline and growth opportunities

Chief of Staff Development

As trust and capability grow, the role will expand toward:

Acting as the founder’s operational right hand
Taking ownership of open-ended business initiatives
Breaking larger priorities into actionable projects
Driving projects forward independently
Coordinating across clients, vendors, and other stakeholders
Identifying operational gaps before they become problems
Helping determine what should remain with the founder versus what can be delegated
Taking increasing ownership of the firm’s overall operations

Hard Skills

3+ years of experience in Executive Assistance, Operations, Project Management, Client Success, or a related role
Experience supporting a founder, executive, business owner, or senior leader strongly preferred
Experience within professional services, finance, accounting, consulting, technology, or an agency environment preferred
Exceptional written and spoken English
Strong calendar and inbox management experience
Strong client communication and follow-up skills
Experience managing multiple workflows and competing priorities
CRM experience and strong data organization skills
Proficiency with Google Workspace and/or Microsoft 365
Comfortable learning modern productivity and project management platforms
Experience with HubSpot, Notion, Asana, ClickUp, or similar tools is a plus
Comfortable using AI tools such as ChatGPT or Claude to improve productivity and workflows

Soft Skills

Highly proactive and self-directed
Exceptional organizational skills
Strong judgment and discretion
High agency and ownership
Resourceful problem solver
Strong attention to detail
Excellent written and verbal communication
Comfortable communicating with executives, clients, and business owners
Able to operate independently without excessive supervision
Adaptable in a fast-growing environment
Comfortable with ambiguity and changing priorities
Long-term oriented and motivated by professional growth
Interested in developing into a leadership role

About The Candidate

The ideal candidate has moved beyond purely task-based administrative work and is ready to become a true operational partner.

They should be able to receive an objective rather than a checklist and determine the steps required to accomplish it.

This person should naturally notice what is missing, what is overdue, what needs follow-up, and what could be improved.

The successful candidate will have the maturity and communication skills to interact directly with clients and senior business leaders while also having the operational discipline to manage the details behind the scenes.

Most importantly, they should have the ambition to grow with the company and eventually take on meaningful responsibility as a Chief of Staff.

Career Progression

Months 1-3: Executive Assistant & Client Operations

Inbox and calendar ownership
Client follow-up
Document tracking
Meeting preparation
Administrative organization
Learning the firm’s clients, systems, and operating rhythm

Months 3-6: Operations Lead

SOP development
CRM ownership
Process improvement
Operational project management
Business development coordination
Increased independent decision-making

Year 1+: Chief of Staff

Broader operational ownership
Strategic project execution
Founder support and prioritization
Cross-functional coordination
Independent management of business initiatives
Building the operational infrastructure required for continued growth

Why This Role Matters

The founder is balancing the growth of the fractional CFO practice with a demanding executive career outside the business.

This hire is intended to create meaningful leverage.

By taking ownership of the company’s operational complexity, client follow-up, organization, systems, and execution, this person will allow the founder to spend more time on the highest-value activities, including client relationships, strategic decisions, and business growth.

For the right person, this is an opportunity to grow from executive support into a genuine Chief of Staff position with significant autonomy and ownership.

Schedule

Full-time, U.S. Pacific Time (PT) alignment required.

Candidates must be comfortable working hours that provide substantial overlap with the founder’s Pacific Time workday.

South African candidates should specifically understand that this may require a later working schedule in South Africa.

As the candidate becomes fully trained and takes greater ownership of the business, there may be flexibility to optimize the schedule around the company’s operational needs.

Location

South Africa, Colombia, and Argentina preferred.

Candidates must have reliable internet, a professional remote working environment, and the ability to consistently work the required U.S. Pacific Time schedule.

Operations Lead & Executive Assistant (Chief of Staff Track)