Contractor Operations and Payroll Specialist

Apply Digital Ltd.; Santiago; Hybrid; CLP 18,000,000 - 30,000,000; Full time

Benefits offered by this job

Flexible work arrangements

Generous vacation policy

AI upskilling support

Customizable benefits

Job summary

APPLY is seeking a Contractor Operations and Payroll Specialist to own end-to-end payroll for contractors, including multi-country invoicing and funding. The role partners with PMO and Finance to ensure accurate payments and compliant workflows across currencies.

Candidates should bring experience in payroll, AP, and contractor lifecycle management, with a proactive mindset and strong Excel/Google Sheets skills. Based in Latin America or Santiago, Chile, with hybrid/remote flexibility.

Qualifications

• 3+ years of payroll, accounts payable, contractor management with multi-country workforce.
• Hands-on experience generating contracts and managing the contractor lifecycle.
• Strong understanding of timesheet-to-invoice-to-payment workflows.
• Experience paying across currencies and jurisdictions is a plus.
• Advanced spreadsheet skills and comfort with large data sets.

Responsibilities

• Generate and issue contractor agreements with internal stakeholders.
• Manage amendments, renewals, and terminations for contractor records.
• Validate onboarding docs and maintain records in Deel/HiBob.
• Coach contractors through onboarding to ensure work readiness on time.
• Coordinate contractor timesheets, invoices and payments across entities.
• Prepare journal entries and support month-end close for contractor population.
• Identify workflow improvements to reduce manual effort and errors.

Skills

Payroll experience

Accounts payable

Contractor management

Multi-country workforce

Timesheet-to-invoice workflow

Journal entries & month-end close

Advanced spreadsheets (VLOOKUP, Pivot)

Google Sheets

Communication skills

Detail-oriented

Ownership mindset

Process improvement

Tools

Deel

HiBob

Job description

ABOUT APPLY

APPLY is the Agentic Customer Experience (ACx) partner for the world's most ambitious consumer and entertainment brands. We bring together deep domain expertise across Retail, CPG, Sports, and Media with AI-native delivery capability, designing and delivering agentic solutions that turn CX vision into commercial reality. We are the partner of choice for brands like Arc'teryx, NFL, Lululemon, and Kraft Heinz. For more information, visit applydigital.com.

LOCATION:

APPLY is hybrid/remote-friendly. The preferred candidate should be based in Latin America, preferably working in hours that align to ET (Eastern Timezone) or PT (Pacific Timezone).

Candidates located in Santiago, Chile are able to work out of our Santiago office as remote/hybrid employees. Candidates located outside of Santiago, Chile will be fully remote employees.

THE ROLE:

As a Contractor Operations and Payroll Specialist you will play a critical role in making sure every contractor who works with APPLY is contracted correctly, paid accurately and on time, and receives an experience held to the same standard as our employees. Reporting to the Payroll Manager, you will own the end-to-end payroll cycle for our contractor population: individual contractors and contractors engaged through third-party agencies. This is a great opportunity for someone who is experienced in Accounts Payable, contracts administration, and payroll processing and is ready to develop an integral specialization for APPLY’s business.

RESPONSIBILITIES:

• Generate and issue contractor agreements for individual contractors and third-party agency contractors, collaborating with legal counsel, PMO and our contractor management vendor when necessary

• Manage amendments, renewals, extensions and terminations, keeping contract records current and audit-ready.

• Collect and validate onboarding documentation and maintain contractor records in Deel and HiBob.

• Coach contractors through onboarding processes and tasks to be work-ready on time.

Payment Management

• Partner with our PMO and Finance teams to make sure contractor timesheets are recorded accurately and on time; validate hours against contracts, rates and approvals.

• Translate approved contractor hours into accurate invoices and resolve variances before payment.

• Prepare, review and release contractor payments on schedule, across currencies and payment methods.

• Investigate payment inquiries and process adjustments, off-cycle payments and corrections to resolve payments discrepancies.

• Manage contractor payment funding across legal entities, forecasting cash needs ahead of each pay run.

• Prepare journal entries for contractors on the month-end close schedule.

• Identify and implement improvements to contractor workflows, reducing manual effort and error across contracting, timesheets, invoicing and funding.

Communications & Support

• Serve as the primary point of contact for contractors and agency partners on invoices and payment questions.

• Respond to inquiries and escalations with accuracy, empathy and discretion, and escalations appropriately.

• Maintain up-to-date process guides and FAQs so contractors and project managers know their responsibilities and deadlines.

REQUIREMENTS:

• 3+ years of experience in payroll, accounts payable, contractor management with a multi-country workforce.

• Hands-on experience generating contracts and managing the contractor lifecycle.

• Strong understanding of timesheet-to-invoice-to-payment workflows.

• Working knowledge of journal entries, accruals, intercompany and multi-entity accounting, and month-end close; comfortable partnering with Finance on reconciliations.

• Advanced spreadsheet skills (VLOOKUPs, Pivot Tables, etc.), preferably Google Sheets, with the ability to reconcile large data sets accurately.

• Fluent spoken and written English, with excellent communication skills and the ability to explain contracts, deadlines and payment issues clearly.

• High attention to detail and a compliance and audit mindset, with the discretion to handle confidential banking, tax and compensation data.

• A high-ownership, proactive mindset, with the curiosity to improve processes and adopt new tools.

Nice to Have

• Experience with Deel, HiBob or comparable global contractor platforms.

• Experience in a professional services, agency or consulting environment with a large contractor population.

• Experience paying across currencies and jurisdictions, and a working awareness of contractor classification and compliance risks.

• Hands-on experience using generative AI tools (such as Claude) to build or improve workflows, reporting or process documentation.

LIFE AT APPLY

People are at the core of everything we do at APPLY. We provide you with modern tools, systems and approaches, value your time, safety, and health, and strive to build a work community where you can thrive and grow. Here are a few benefits we offer to support you:

Agentic Delivery:

Our people work in a modern way to deliver client outcomes. Broaden your skills on a range of engagements with international brands that have a global impact.

An inclusive and safe environment:

We’re truly committed to building a culture where you are celebrated and everyone feels welcome and safe.

AI & Strategic Upskilling:

Accelerate your professional growth with generous training budgets and mentorship, with a specific focus on Agentic AI expertise and the critical human skills required for the future of work.

Generous vacation policy:

Work-life balance is key to our team’s success, so we offer ample time away from work to promote overall well-being.

Customizable benefits:

Tailor your extended health and dental plan to your needs, priorities, and preferences.

Flexible work arrangements:

We work in a variety of ways, from remote, to in-office, to a blend of both.

APPLY is a safe, respectful, and inclusive community where differences are celebrated. We are committed to equal opportunity and fostering a workplace where everyone belongs. Learn more in our Diversity, Equity, and Inclusion (DEI) section. For recruitment accommodations, please email [e-mail].