Senior Manager, Regulatory Compliance and Licensing

As a seasoned compliance leader, you know that strong regulatory functions depend on clear ownership, capable teams, disciplined execution, and sound judgment. You bring meaningful experience leading regulatory compliance operations in a highly regulated environment. You can translate complex requirements into practical processes, challenge and support subject matter experts, and build the management systems needed to execute regulatory obligations consistently. You are equally comfortable developing teams, engaging with regulators and external partners, partnering with Legal and business leaders, and communicating risks and priorities to senior leadership.

Responsibilities

Provide people and operational leadership across Regulatory Compliance and Licensing Operations within Product Compliance; Set clear priorities, ownership, operating rhythms, and performance expectations; Develop team members and build capabilities for consistent regulatory execution; Establish clear ownership, documented processes, effective controls, escalation paths, and backup coverage for critical regulatory obligations; Reduce single points of failure through cross-training, business continuity planning, and knowledge management; Ensure timely, accurate, and compliant execution of key obligations, including PEO and other applicable licensing, CPEO certification, ESAC accreditation, regulatory reporting, government filings, and regulatory examinations; Oversee interactions with regulators, government agencies, auditors, and external partners; Lead the function in monitoring and interpreting regulatory developments and assessing their impact on products and operations; Partner with Payroll Compliance, Legal, Product, Engineering, Operations, and other stakeholders on implementation of regulatory requirements; Partner on strengthening controls and remediation, and support audit and examination readiness; Serve as a senior advisor on regulatory requirements, operational impacts, and risks; Build, coach, and develop an engaged, high-performing team, and assess capabilities and capacity

Requirements

10+ years of progressive experience in regulatory compliance, licensing, tax compliance or research, compliance operations, or a related field; 5+ years of people leadership experience, including leading teams responsible for complex regulatory or compliance obligations; Experience leading regulatory compliance programs in a highly regulated environment; Strong regulatory judgment and demonstrated ability to translate complex requirements into operational processes, controls, and clear ownership; Demonstrated experience strengthening or scaling compliance operations, including process documentation, business continuity, controls, and performance management; Experience working with government agencies, regulators, auditors, Legal, and cross-functional business partners; Demonstrated ability to identify and manage regulatory, operational, and business continuity risks; Strong people leadership, coaching, and performance management skills; Exceptional written and verbal communication skills, including the ability to communicate risks and priorities to senior leaders; Proven ability to influence and drive outcomes across functions

Nice to have

Experience in PEO, payroll, HR technology, fintech, SaaS, or another regulated technology-enabled environment; Experience with CPEO certification, ESAC accreditation, state PEO licensing, or similar regulatory programs; Experience leading regulatory change management, or a comparable regulatory interpretation function; Experience strengthening compliance functions through organizational, process, or control improvements; Familiarity with internal audit, SOX, SOC, or other control and assurance frameworks; Experience using technology, automation, or AI to improve compliance operations

Benefits

Welcoming and casual environment; great benefits; wellness program offerings; company retreats; ability to interact with and learn from leaders in the startup community; Total Rewards and perks offered to team members