Operations Lead & Executive Assistant (Chief of Staff Track)

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

LocationRemote, South Africa, Colombia, or Argentina

ScheduleFull-time, aligned with U.S. Pacific Time (PT)

Employment TypeFull-Time Independent Contractor

Reports ToFounder & 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.