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Leads Gusto’s commercial insurance servicing team, overseeing licensed account managers, service quality, escalations, carrier relationships, compliance, and performance metrics. The role develops SOPs, improves automation, partners with product and engineering, manages complex Workers’ Compensation servicing issues, coaches staff, and supports hiring and team growth. It requires commercial lines experience, strong Workers’ Compensation knowledge, carrier portal expertise, AI and automation fluency, supervisory compliance capability, and an active Property & Casualty producer license.

Owns end-to-end servicing for a small commercial insurance book, including endorsements, certificates, coverage questions, audits, billing disputes, cancellations, renewals, claims intake, and reinstatements. Serves as liaison among insureds, carriers, and licensed producers; uses payroll data for proactive coverage outreach; documents recurring cases as product requirements; partners with product and engineering on automation; and establishes SOPs, escalation paths, and service standards.

Conduct complex enhanced due diligence and KYC investigations for high-risk customers and entities. Research adverse media, sanctions, PEPs, source of wealth and funds, beneficial ownership, and geographic or industry risks. Prepare investigative summaries and SARs, resolve escalated alerts, make risk-based onboarding and exit recommendations, validate AI-generated research, improve investigative workflows, and mentor junior analysts.

Conduct complex fraud investigations involving account takeover, business email compromise, identity theft, payment fraud, and social engineering. Analyze transaction, authentication, communication, and external intelligence data; document investigative narratives; prepare Unusual Activity Referrals; recommend risk-based remediation; support customer and fund recovery efforts; use AI-enabled tools; collaborate with Risk, Compliance, Product, Engineering, and Data Science; and mentor junior analysts.

Manage and grow a portfolio of strategic accounting firm partners for Gusto Pro. Responsibilities include account planning, QBRs, partner acquisition, renewals, upsells, contract negotiation, enablement, product adoption, executive relationship management, pipeline reporting, and cross-functional product feedback. The role requires frequent partner engagement, AI-enabled workflows, CRM and sales software experience, and travel to partner meetings and industry events.

Finance Intern supporting Gusto’s Finance, BizOps & Strategy team through financial and operational reporting, cost and margin analysis, roadmap projects, and ad hoc analysis. The role partners cross-functionally with Customer Experience, EPD, and Corporate Development teams, translating financial data into business decisions. Interns will use Excel, Google Sheets, AI tools, and automation while communicating findings to non-finance stakeholders.

Lead full-cycle recruiting for design and specialized technology roles, from search strategy through offer acceptance. Build sourcing pipelines, advise hiring leaders with market and data insights, deliver high-touch candidate experiences, and partner cross-functionally to keep hiring moving. Use AI to improve sourcing and interview processes, flex into product management and data searches, and build Gusto’s San Francisco design community through events and relationships.

Manage and coach a pod of 10–12 quota-carrying Account Executives toward multi-product quota attainment, pipeline health, and activity targets. Conduct weekly one-on-ones, call reviews, roleplays, and development planning. Partner with RevOps, Product Marketing, Product, and Sales Enablement on sales strategy and positioning. Own two to three team OKRs and drive cross-functional initiatives supporting upsell and cross-sell growth.

Manage 401(k) plan conversions from initial handoff through asset transfer and first contribution. Gather documentation, reconcile data, guide plan sponsors and administrators, monitor activation and readiness benchmarks, prevent process delays, and serve as the primary client contact. Partner with Operations, Sales, and Legal on complex plan changes and compliance requirements while using AI tools to improve workflows and communications.

Own and expand Gusto’s third-party integrations, building reliable Ruby on Rails and Sidekiq backend services that synchronize data with partner platforms. Evaluate traditional APIs and AI agent protocols such as MCP, shape the technical roadmap, collaborate with Product, Design, and Data Science, establish engineering practices, review code, and mentor engineers. The role requires end-to-end project ownership in an ambiguous, evolving domain.