Senior Director, Contractor Analytics & Compliance - Remote

Ladders; United States; Remote; USD 143,000 - 286,000; Part time

Benefits offered by this job

Medical, vision, and dental

401(k)

PTO including sick and parental leave

Disability insurance

Tuition reimbursement

Job summary

Ladders seeks a Senior Director, Business Analysis and Insights (Independent Contractors) to lead contractor earnings, tax, and compliance initiatives in a fast-moving Retail & Consumer Goods setting. Remote position with global partnership across finance, engineering, data science, and ops to deliver scalable, data-driven processes that support reporting accuracy and regulatory adherence.

The role combines strategic oversight with hands-on execution, guiding cross-functional teams to align with

Qualifications

• Bachelor's degree in a related field or 8 years of relevant experience.
• Deep expertise in fintech, compliance, or tax technology.
• Hands-on experience working with engineering and data science teams.
• Experience leading large, global, multidisciplinary teams.
• Ability to design solutions that meet regulatory requirements across jurisdictions.

Responsibilities

• Define and execute the strategic roadmap for contractor earnings and tax initiatives.
• Oversee accurate and timely disbursement of earnings and tax reporting for contractors.
• Design solutions that embed compliance and minimize regulatory risks.
• Drive continuous innovation through user research and competitor benchmarking.
• Lead cross-functional teams to deliver scalable solutions aligned with business metrics.

Skills

Fintech expertise

Regulatory compliance

Tax technology

Cross-functional leadership

Data collaboration

Education

Bachelor's degree or 8+ years experience

Job description

Ladders seeks a Senior Director, Business Analysis and Insights (Independent Contractors) to lead contractor earnings, tax, and compliance initiatives in a fast-moving Retail & Consumer Goods setting. Remote position with global partnership across finance, engineering, data science, and ops to deliver scalable, data-driven processes that support reporting accuracy and regulatory adherence.

The role combines strategic oversight with hands-on execution, guiding cross-functional teams to align with