Administrative & Support Services Expert Contributor | Freelance

Crossing Hurdles; United States; Remote; USD 10,000 - 12,000; Full time

Job summary

Crossing Hurdles is seeking Administrative & Support Services experts to work remotely on a task-based AI training project. You will craft realistic workplace tasks using your real professional experience and provide supporting evidence and ideal deliverables.

This is not generic data labeling; it requires professional workflows and documentation. You will develop scenarios across business operations, customer support, HR, payroll, and scheduling, and define evaluation criteria to assess AI

Qualifications

• Strong expertise in Administrative & Support Services or related field.
• Experience handling real-world, multi-step workflows.
• Familiarity with U.S. workplace practices and terminology.
• Strong analytical thinking and attention to detail.
• Ability to create and interpret professional reports, spreadsheets, schedules, HR documents.
• Excellent written English and professional communication.
• Ability to work independently in a remote environment.

Responsibilities

• Use a real admin or support workflow you have personally handled to create a realistic task.
• Create scenarios involving business ops, customer support, staffing, payroll, HR, scheduling, or service delivery.
• Provide anonymized supporting materials such as reports, spreadsheets, schedules, HR documents, payroll materials, or policies.
• Complete the task yourself and deliver the ideal professional deliverable or solution.
• Define clear evaluation criteria to assess the accuracy, completeness, and quality of an AI-generated response.
• Ensure tasks reflect realistic professional reasoning, decision-making, and workplace practices.
• Work independently and complete assigned tasks within the required timelines.

Skills

Administrative & Support Services

Real-world workflows

US workplace practices

Analytical thinking

Reports & documents

Written English

Remote independent work

Job description

Job description

Employment Type: Freelance / Contract (Work from Home)
Qualification: Relevant professional experience in Administrative Services, Business Operations, Customer Support, HR Operations, Staffing, Payroll, or related fields
Project Duration: Task-based freelance project
Time Commitment: ~4 hours per task
Compensation: 10,000 per accepted task

About the Role

We are hiring Administrative & Support Services Experts for a remote, task-based AI training and evaluation project. The selected experts will use their real professional experience to create realistic workplace tasks that help AI systems understand how administrative and support professionals actually work. This is not a data-labeling, generic content-writing, or academic question-answering role. The work involves creating realistic professional scenarios, providing supporting evidence, developing the ideal solution, and defining evaluation criteria.

Key Responsibilities

• Use a real administrative or support-services workflow you have personally handled to create a realistic workplace task.


• Create professional scenarios involving business operations, customer support, staffing, payroll, scheduling, HR operations, service delivery, or administrative workflows.


• Provide safe, anonymized, or realistic supporting materials such as reports, spreadsheets, schedules, customer records, HR documents, payroll materials, policies, or other relevant files.


• Complete the task yourself and create the ideal professional deliverable or solution.


• Define clear evaluation criteria to assess the accuracy, completeness, and quality of an AI-generated response.


• Ensure tasks reflect realistic professional reasoning, decision‑making, and workplace practices.


• Work independently and complete assigned tasks within the required timelines.

Required Skills

• Strong professional expertise in Administrative & Support Services or a related field.


• Experience handling real‑world, multi‑step professional workflows.


• Familiarity with U.S. workplace practices, standards, terminology, or U.S.-facing/global operations is highly preferred.


• Strong analytical thinking and attention to detail.


• Ability to create and interpret professional reports, spreadsheets, schedules, customer records, HR documents, or other relevant materials.


• Strong written English and professional communication skills.


• Ability to work independently in a remote environment.


• Comfortable working on AI training and evaluation projects.

Relevant Backgrounds

Business Operations | Administrative Operations | Customer Support | Customer Operations | HR Operations | Staffing | Payroll | Workforce Management | Service Delivery | Scheduling | Shared Services | Related Roles

U.S.-Based Company Experience

Experience with companies such as Concentrix, TTEC, TaskUs, ADP, Kelly Services, Robert Half, ManpowerGroup, or Randstad can be relevant.

These companies are provided only as examples for reference. Candidates with experience in any similar U.S.-based company or U.S.-facing/global organization are welcome to apply.