Licensing Program Manager

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 offers payroll processing for hundreds of thousands of businesses and their employees, and that activity is supervised by state money transmission regulators across the country. Our financial services licenses are foundational to how Gusto operates, and keeping that portfolio current, accurate, and examination-ready is mission critical. Gusto is looking for a hands-on regulatory compliance professional to own the day-to-day management of Gusto's licensing portfolio. You will run the licensing lifecycle end to end across NMLS and non-NMLS states: applications, renewals, amendments, change notices, periodic reporting, surety bonds, and ongoing license conditions. You will also serve as a core contributor in state examinations, managing request lists, evidence, and commitments This is an individual contributor role reporting to the Head of Financial Services. At Gusto, Legal & Compliance operates as an AI-native team. You will use and help improve AI-enabled licensing workflows, including our licensing and examination registries, filing calendars, and regulatory change tracking, with appropriate human-in-the-loop controls for accuracy and accountability. About the Team: Gusto’s Legal & Compliance team partners closely with product and engineering teams to enable innovation, facilitate responsible company growth, accelerate Gusto’s roadmap, and deliver compliant products to our customers. We are passionate about applying AI-native ways of working, thoughtful compliance risk management, and a daily service mindset to improve the experience of small business owners and their employees. Each team member is an owner, a trusted advisor, and a meaningful contributor to Gusto’s mission. Here’s what you’ll do day-to-day: • Own day-to-day management of Gusto's money transmitter (MTL) and related state financial services licenses, maintaining a current system of record for every license, condition, and deadline. • Manage Gusto's NMLS company record end to end (MU1, MU2, MU3 filings, amendments, and disclosure updates), and run the annual NMLS and state renewal cycles. • Prepare and file new license applications, expansion filings, and change notices or amendments, partnering with counsel and managing regulator approvals for changes in control, officers, or business activities. • Own the quarterly NMLS MSB Call Report and state periodic, annual, and transaction volume reports, coordinating with Finance and Treasury on financial statement, net worth, and investment reporting. • Manage the surety bond portfolio and the regulatory filing calendar, ensuring on-time filings with documented evidence for examination. • Serve as a key contributor on state and multi-state examinations, managing request lists, evidence collection, document production, and quality control. • Support examination findings and license conditions through to closure, coordinate high-risk data requests, and manage regulator correspondence, escalating substantive matters. • Monitor state money transmission developments (MTMA adoption, NMLS/CSBS and rule changes) and assess their impact on Gusto's licenses and filings. • Translate licensing requirements into clear procedures, checklists, and guidance for cross-functional partners. • Use AI-enabled tools to automate filing prep, deadline tracking, and evidence assembly with documented human review, and identify gaps to make the program more scalable and examination-ready. Here’s what we're looking for: • 5+ years of experience in regulatory compliance, licensing, or regulatory operations at a fintech, payments company, money services business, or regulated financial institution, including at least 3 years managing money transmission licenses; experience with additional state license types (lending, servicing, collections, PEO) or at a high-growth fintech operating through sponsor bank or embedded finance partnerships is a plus. • Experience with PEO licensing is a plus, particularly for candidates who have operated across both MTL and PEO licensing regimes. • Paralegal background preferred, especially with experience on regulatory filings, licensing documentation, or change of control notices. • Hands-on NMLS expertise, including MU1, MU2, and MU3 filings, the annual renewal cycle, the MSB Call Report, and Electronic Surety Bonds. • Working knowledge of state money transmission requirements, including net worth, permissible investments, surety bonds, change of control, authorized delegates, and periodic reporting. • Direct experience supporting state or multistate regulatory examinations, including request list management, evidence assembly, and findings remediation; familiarity with CSBS multi-state examination frameworks like One Company One Exam and MMET is a plus. • Rigorous documentation discipline: every filing accurate, every deadline tracked, every submission retained. A Notary Public commission, or willingness to obtain one, is a plus. • Strong organizational and project management skills, with the ability to manage high-volume, de