Senior Compliance Manager

Senior Compliance Manager

Salary Range: $110,000 – $120,000

Reporting to: Executive Vice President/Chief Operating Officer (EVP/COO)

Location: Remote (East Coast preferred)

Start Date: Immediate

End Date: December 2026 with potential to continue

Position Summary

Way to Win is seeking a Senior Compliance Manager to support advocacy, political, and programmatic operations across the organization’s multi-entity structure. This role will work closely with the Executive Vice President/Chief Operating Officer (EVP/COO) and collaborate across program, communications, political, and operations teams to ensure compliance with federal, state, and local regulations governing lobbying, advocacy, charitable organizations, and political activity.

The Senior Compliance Manager will oversee lobbying compliance, independent expenditure reporting, regulatory registrations, and internal compliance review processes, while also helping identify and mitigate compliance risks associated with advocacy campaigns, messaging, vendor contracts, and program activities.

This role will also manage charitable solicitation registrations, business registrations, and related regulatory filings, working with internal teams and external vendors to ensure accurate and timely compliance across jurisdictions.

The Senior Compliance Manager will serve as an internal resource to staff across departments, helping ensure Way to Win’s work is conducted in accordance with applicable legal and regulatory frameworks while supporting the organization’s long-term strategy and mission.

This is an exempt position. Exempt employees are expected to work the appropriate and necessary time required to complete key assignments and responsibilities.

Essential Duties and Responsibilities

Compliance Review, Grantmaking, and Contract Operational Support (45%)

• Conduct initial compliance reviews of grantmaking strategies, messaging, advocacy scripts, campaign materials, program initiatives, and communications content to identify potential regulatory risks prior to legal review.
• Review grant recommendations, regranting structures, and funding allocations across c3, c4, PAC, and LLC entities to ensure alignment with applicable legal and compliance requirements.
• Conduct initial compliance reviews of messaging, advocacy scripts, campaign materials, program initiatives, and communications content to identify potential regulatory risks prior to legal review.
• Review consultant and vendor contracts to identify potential compliance considerations related to lobbying, advocacy, political activity, and regulatory obligations before routing for legal review.
• Collaborate with program, communications, and political teams to ensure proposed activities align with applicable compliance guidelines.
• Flag potential compliance risks early and work with leadership to address them before activities are implemented.
• Support the development of internal processes to improve compliance oversight across the organization.

Lobbying, Political Compliance, and Gift Rules (30%)

• Prepare and oversee lobbying registrations and periodic reports across multiple jurisdictions for review and approval by the EVP/COO.
• Maintain and manage a comprehensive lobbying reporting calendar, coordinating with internal staff and partners to collect required reporting information.
• Manage the organization’s lobbying time tracking system, including onboarding staff, maintaining accurate records, troubleshooting issues, and coordinating updates with IT.
• Review lobbying time reports and related expenses to identify activities that may trigger new lobbying registrations or reporting obligations.
• Support independent expenditure reporting, including tracking political spending activity and preparing required campaign finance filings in compliance with federal, state, and local regulations.
• Maintain internal guidance and resources related to lobbying rules, ethics regulations, and political compliance requirements.
• Respond to internal inquiries from staff regarding lobbying, advocacy, and political compliance considerations.
• Monitor changes in laws and regulations affecting lobbying, advocacy, independent expenditures, and political activity.
• Assist in gathering documentation and materials required for regulatory audits or reviews.

Charitable Solicitation and Business Registrations (20%)

• Serve as the primary internal contact for vendors supporting state and local charitable solicitation registrations, annual filings, and business registrations.
• Coordinate with vendors and internal teams to prepare and submit required filings in jurisdictions where Way to Win operates or conducts fundraising activities.
• Develop processes to gather necessary information from internal teams and partners to ensure accurate and timely filings.
• Research jurisdiction-specific registration and reporting requirements and update internal compliance processes accordingly.
• Maintain organized records of filings and registration statuses across jurisdictions.

Materials, Guidance, and Training Support (5%)

• Support the preparation and delivery of compliance trainings and guidance materials for internal teams.
• Maintain internal resources related to lobbying compliance, advocacy regulations, political reporting, and organizational compliance policies.
• Assist with preparing compliance guidance for staff engaged in advocacy, fundraising, communications, and political activities.

Knowledge, Skills, and Abilities

• Strong understanding of lobbying regulations, political compliance rules, and ethics requirements.
• Knowledge of legal frameworks governing organizations exempt under Sections 501(c)(3), 501(c)(4), and 527 of the Internal Revenue Code.
• Familiarity with independent expenditure reporting and campaign finance regulations.
• Experience managing regulatory reporting processes and compliance tracking systems.
• Strong project management and organizational skills with the ability to track multiple regulatory deadlines.
• Excellent written and verbal communication skills and ability to collaborate across teams.
• Ability to work independently within a fast-paced, deadline-oriented environment.
• Strong attention to detail and ability to handle confidential information with discretion.
• Strong analytical and problem-solving skills with sound judgment in identifying compliance risks.

Education and Experience

Required

• 3-5+ years of experience in advocacy, lobbying, political, or nonprofit compliance
• Experience with regulatory filings and compliance tracking systems
• Familiarity with Salesforce, Google Workspace, or similar systems

Preferred

• Working experience with independent expenditure reporting or campaign finance compliance
• Working experience managing charitable solicitation registrations and business registrations
• Experience working within multi-entity nonprofit or political organizations on bookkeeping functions

Resumes should be emailed directly to careers@waytowin.us

Way To Win offers a fully remote environment and is proud to offer a robust benefits package:

• Health Care - Comprehensive and robust 100% employee and family paid health care coverage to all employees.
• Retirement Plan - employees are fully vested in the company’s retirement plan 90 days after their start date. Way to Win contributes 6% of the base salary to the employee’s retirement account, regardless of whether the employee contributes or not.
• Life, Short-term Disability, Long-term Disability, and AD&D - Employer-paid Life Insurance, Disability and AD&D.
• Unlimited Paid Time Off.
• Office Closure - 30 days of holiday time, this includes a Spring break, Summer break, Thanksgiving break and an EOY break.
• FSA - Three different tax-deferred FSA accounts (funded by employees) – Health, Commuter (transit/parking — including UberPool), and Dependent Care.
• HRA ($2,000 p/y)
• Family Leave -12 weeks of paid Family Leave for the birth, adoption, or fostering of a child after one full year of employment.