Job Overview
Location
Remote (US)
Job Type
Full-time
Category
Software Engineering
Date Posted
March 21, 2026
Full Job Description
đź“‹ Description
- • As the first dedicated Fraud & Risk Operations Lead at Fitt Insider Inc., you will play a critical role in safeguarding the company’s mission to enable consumers to pay for eligible health & wellness expenses using HSA/FSA funds. Your work will directly protect customers, partners, and the business from financial and reputational harm while ensuring seamless, low-friction approval experiences that support growth and trust in the platform.
- • You will own the end-to-end lifecycle of fraud and risk management—from real-time detection and investigation to remediation and prevention—building foundational systems, processes, and controls from the ground up in a fast-moving, mission-driven health & wellness fintech environment.
- • Day to day, you will detect, triage, and respond to fraud attacks such as card testing, account takeover, refund/chargeback abuse, and synthetic identity using internal and external tools; own incident response for risk events by containing, investigating, documenting, and driving remediation; and participate in on-call or escalation coverage as needed to ensure timely resolution.
- • You will conduct high-judgment investigations and make consistent allow/deny/hold decisions for transactions, accounts, and partner activity, while building decision frameworks and escalation paths that balance fraud loss, customer experience, and regulatory/compliance constraints.
- • You will own dispute operations end-to-end, including monitoring and responding to dispute inquiries/alerts, managing customer communications, gathering evidence, submitting representments, and managing deadlines; maintain clean case notes and audit trails; and analyze dispute reason codes and inquiry drivers to implement prevention tactics that reduce repeat disputes and friendly fraud.
- • You will define and track core risk metrics such as fraud loss, net loss, chargeback rate, approval rate, manual review rate, false positives, and backlog health; build reporting dashboards; and propose/implement controls including velocity rules, blocklists/allowlists, step-up verification, 3DS/issuer strategy, and policy updates.
- • You will collaborate closely with Product, Engineering, and Data teams to translate fraud patterns into tooling and product improvements—such as enhanced signals, rules, internal admin tools, and case management systems—and manage external relationships with processors, acquirers, fraud vendors, and card networks/issuers to drive root-cause fixes.
- • You will work cross-functionally with Ops/Support, Finance, and Legal to identify root causes of risk issues and ship sustainable fixes that stick, while advocating for the customer experience in risk decision-making.
- • In this role, you will have the unique opportunity to shape the fraud and risk function from zero to one, gaining deep expertise in payments risk, dispute management, and cross-functional systems design while making a tangible impact on a growing platform that supports consumer health and wellness.
- • You will develop leadership and strategic thinking skills by building scalable processes, mentoring future team members, and influencing product and policy decisions that affect millions of users and partner brands like Eight Sleep, WHOOP, Momentous, and Peloton.
🎯 Requirements
- • 3+ years of experience in fraud, risk, trust & safety, investigations, or payments operations within a fintech, payments platform, marketplace, or high-scale consumer product environment.
- • Strong payments fundamentals, including understanding of card-not-present risk patterns, dispute and chargeback mechanics (including inquiries), and how controls affect approval rates and customer experience.
- • Strong analytical abilities with comfort using SQL, building dashboards, and measuring the impact of interventions to drive data-informed decisions.
- • Demonstrated ability to navigate ambiguous, 0→1 operating challenges—defining processes, setting metrics, creating playbooks, and iterating quickly in fast-paced environments.
- • Excellent written and verbal communication skills, with the ability to remain calm, precise, and effective during high-pressure incidents.
- • High integrity and sound judgment when handling sensitive data and making customer-impacting decisions.
🏖️ Benefits
- • Opportunity to be the first fraud hire and build the fraud & risk function from the ground up, with significant autonomy and impact.
- • Fully remote work arrangement (US-based), offering flexibility and work-life balance.
- • Collaboration with mission-driven health & wellness brands including Eight Sleep, WHOOP, Momentous, Peloton, and others.
- • Exposure to cutting-edge payments, fraud detection, and risk management technologies and methodologies.
- • Professional growth in a high-impact role that combines operations, analytics, product, and cross-functional leadership.
- • Competitive compensation and benefits package aligned with industry standards for senior risk operations roles.
Skills & Technologies
Senior
Remote
About Fitt Insider Inc.
Fitt Insider Inc. is a media and data company that covers the business of fitness and wellness. Through newsletters, podcasts, market research reports and a searchable database, it tracks funding, M&A, emerging brands and consumer trends across gyms, nutrition, wearables, digital health and active lifestyle sectors, serving investors, operators and job-seekers with actionable insights.
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