Enhanced Due Diligence Investigations Analyst

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role: Gusto is seeking a Senior Enhanced Due Diligence (EDD) Investigations Analyst to support our Financial Crime Compliance (FCC) program. This is an individual contributor role within the EDD Investigations team, focused on conducting the most complex due diligence reviews to identify, assess, and mitigate regulatory, financial crime, and reputational risk. In this role, you will independently perform in-depth EDD investigations for the highest-risk customers and most complex entity structures, using a combination of human judgment, open-source intelligence, and AI-enabled tools. You will provide specialized risk analysis to internal partners and make well-supported recommendations on onboarding, monitoring, and exit decisions, balancing regulatory obligations and customer experience. EDD at Gusto presents unique and intellectually engaging challenges. Our platform supports hundreds of thousands of small businesses across diverse industries, ownership structures, and geographies, which means no two investigations look exactly alike. From onboarding through ongoing monitoring, you’ll work through nuanced risk profiles and layered entity structures that require rigor, sound judgment, and adaptability. This role is ideal for someone who can balance a high volume of reviews with deep, independent investigative work on complex matters, and who uses AI as a core part of how they work to improve both efficiency and quality. About the Team: The Enhanced Due Diligence Investigations team conducts thorough reviews of higher-risk customers and activities, from the point of onboarding through ongoing monitoring. The team performs Know Your Customer (KYC) reviews to verify that new customers are legitimate businesses, and evaluates ownership and control structures, source of wealth and funds, adverse media, sanctions exposure, and other risk indicators to ensure Gusto meets regulatory expectations and maintains platform integrity. Here’s what you’ll do day-to-day: • Independently conduct enhanced due diligence reviews for the highest-risk customers in accordance with internal procedures and regulatory expectations, including periodic and event-driven reviews • Perform in-depth open-source research and documentation analysis to assess adverse media, sanctions and PEP exposure, industry and geographic risk, source of funds and wealth, and beneficial ownership and control structures • Evaluate the most complex or multi-layered entities, synthesize findings into clear investigative summaries, and draft Suspicious Activity Reports (SARs) when appropriate • Investigate and independently resolve EDD-related alerts involving sanctions exposure, adverse media, PEPs, marijuana-related businesses, or other elevated risk indicators, making sound, risk-based recommendations and escalating to EDD leadership where guidance is needed to resolve an issue • Independently perform KYC reviews during customer onboarding, verifying business legitimacy, identity, and beneficial ownership, and resolving complex or escalated cases, including those with opaque ownership structures, high-risk indicators, or conflicting information, with minimal guidance • Leverage AI-enabled tools to accelerate issue spotting, alert triage, research, and documentation, providing clear context and constraints through prompt refinement while maintaining human judgment and accountability • Critically review and edit AI-generated research or summaries to ensure accuracy, completeness, and regulatory soundness, applying Gusto's AI policies and data protection standards when handling sensitive information • Identify opportunities to improve investigative workflows, contribute to EDD desktop guides and training materials, and surface insights on emerging trends to support continuous program improvement • Mentor junior analysts on open-source research, beneficial ownership analysis, and risk documentation through case reviews and structured feedback Here’s what we're looking for: • 5+ years of experience conducting enhanced due diligence, AML investigations, KYC, customer due diligence, or similarly deep investigative or research-driven work • Strong investigative writing skills with the ability to independently summarize highly complex fact patterns and risk assessments • Excellent research and analytical skills, including comfort working with large volumes of information • Extensive experience conducting open-source research and adverse media analysis • Deep familiarity with regulatory expectations related to EDD, SAR reporting, and customer due diligence • Ability to apply sound, independent judgment in ambiguous or higher-risk scenarios • Strong organizational skills and attention to detail, comfortable managing multiple complex cases simultaneously • Experience using AI-enabled tools as part of day-to-day investigative workflows, including refining prompts and validating outputs • Collaborative mindset and ability to work effectively with cross-functional teams • Experience mentoring or providing structure