About The Position

Lead the future of independent contractor earnings and tax operations as the Director of Earnings & Tax Excellence. In this role, you will architect innovative, compliant, and user-focused solutions that empower millions of gig workers to receive accurate earnings, meet tax requirements, and trust the systems supporting their livelihoods. This is a rare, high-impact opportunity to shape breakthrough fintech products at scale, blending strategy, technology, and compliance.

Requirements

  • Bachelor's degree in Business, Analytics, Statistics, or related field and 5 years' experience in data analytics, project management, business, or related area OR 7 years' experience in data analytics, project management, business, or related area.
  • Deep expertise in fintech, compliance, or tax technology, with a proven track record of building, launching, and scaling complex products that address regulatory and operational challenges in dynamic environments.
  • Advanced technical fluency, including hands-on experience collaborating closely with engineering and data science teams to develop ML/AI-powered platforms that deliver predictive insights and actionable recommendations to end users.
  • Demonstrated success designing and implementing solutions that meet or exceed regulatory requirements across multiple jurisdictions, maintaining transparency, auditable systems, and proactive risk management frameworks.
  • Strong experience leading and developing large, multidisciplinary teams in global settings, with an ability to foster a culture of innovation, accountability, and cross-functional alignment.
  • A results-driven approach, with a history of driving innovation, navigating ambiguity, and delivering measurable impact in highly regulated, fast-paced industries.
  • 3 years' experience using intermediate functionality of Microsoft Office.
  • 4 years' supervisory experience.

Nice To Haves

  • Consulting experience.
  • Experience working on cross-functional teams or projects.
  • Masters in Business.
  • Project Management Professional Certification.
  • Six Sigma Certification.

Responsibilities

  • Define and execute the long-term vision and strategic roadmap for contractor earnings and tax excellence, ensuring the development of future-ready platforms that drive both user satisfaction and regulatory compliance.
  • Build and oversee capabilities that guarantee accurate, timely disbursement of earnings, seamless tax reporting for contractors (such as 1099s and global equivalents), and transparent, user-centric experiences that foster trust.
  • Design and implement solutions that embed compliance-by-design principles, proactively minimizing regulatory risk while enhancing transparency and reliability for all users.
  • Identify and pursue opportunities for continuous innovation by leveraging competitor benchmarking, in-depth user research, and analysis of industry trends to ensure our offerings remain best-in-class.
  • Lead and align cross-functional teams—including product, engineering, compliance, analytics, and design—to deliver against key business metrics, translating complex requirements into intuitive, scalable solutions.

Benefits

  • Competitive pay and performance-based bonus awards.
  • Health benefits including medical, vision, and dental coverage.
  • Financial benefits including 401(k), stock purchase, and company-paid life insurance.
  • Paid time off benefits including PTO, parental leave, family care leave, bereavement, jury duty, and voting.
  • Short-term and long-term disability.
  • Company discounts.
  • Military Leave Pay.
  • Adoption and surrogacy expense reimbursement.
  • Live Better U education benefit program for full-time and part-time associates.

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What This Job Offers

Job Type

Full-time

Career Level

Senior

Industry

General Merchandise Retailers

Education Level

Bachelor's degree

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