Application Guide

How to Apply for Chief Financial and Administrative Officer

at The Clean Slate Initiative

šŸ¢ About The Clean Slate Initiative

The Clean Slate Initiative (CSI) is a newly independent nonprofit (est. 2024) leading a rare bipartisan effort to automate record sealing for the 70ā€“100 million Americans with arrest or conviction records. With a 48-person remote team, active campaigns in red and blue states, and a growing focus on the South, CSI offers a unique chance to blend financial stewardship with criminal justice reform at a pivotal growth moment. Working here means shaping the infrastructure of a multi-entity organization (501(c)(3) and 501(c)(4)) while directly expanding economic opportunity for millions.

About This Role

As Chief Financial and Administrative Officer, you will own the financial, operational, and administrative backbone of a fast-scaling national nonprofit and its affiliated 501(c)(4). You will design and lead budgeting, compliance, HR, IT, and risk management across a remote, multi-entity structureā€”while ensuring every dollar and process supports CSIā€™s ambitious legislative and implementation goals. This is a hands-on executive role for someone who thrives in building systems from scratch and wants their financial leadership to directly fuel social impact.

šŸ’” A Day in the Life

Your day might start with a quick check-in with the finance team on cash flow and grant reporting, followed by a meeting with program leads to refine the budget for a new state campaign. After lunch, youā€™d review HR policies for a remote hire in the South, then join a board finance committee call to present the latest multi-entity financials. Youā€™ll end the day troubleshooting an IT security question and updating the executive team on compliance deadlinesā€”all while keeping CSIā€™s mission to expand record relief at the center of every decision.

šŸš€ Application Tools

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Interview Prep

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šŸŽÆ Who The Clean Slate Initiative Is Looking For

  • Proven experience as a CFO/COO or senior finance leader in a multi-entity nonprofit (ideally with both 501(c)(3) and 501(c)(4) experience) and a track record of scaling financial infrastructure from $10M+ to $25M+ budgets.
  • Deep knowledge of nonprofit accounting (GAAP, fund accounting, grant compliance, Form 990) and experience managing audits, 990s, and board finance committees for separate boards.
  • Demonstrated ability to lead administrative functionsā€”HR, IT, operations, and complianceā€”in a fully remote, geographically dispersed organization, with a bias toward building equitable, transparent processes.
  • A strategic partner to program and executive teams who can translate campaign and advocacy goals into financial models, dashboards, and risk assessments, and who is passionate about criminal justice reform and racial equity.

šŸ“ Tips for Applying to The Clean Slate Initiative

1

Highlight any experience with 501(c)(4) organizations or multi-entity structuresā€”CSIā€™s dual-board model is uncommon and central to this role, so name specific examples of managing separate legal entities, inter-entity agreements, and compliance.

2

Quantify your scaling experience: instead of 'managed budgets,' say 'grew annual budget from $8M to $22M while adding 30 staff across 15 states, implementing new accounting software and a remote HRIS.'

3

Connect your financial leadership to CSIā€™s missionā€”mention how youā€™ve supported advocacy or direct-service organizations, and why automated record sealing resonates with you personally or professionally.

4

Address the remote-first context directly: describe how youā€™ve built financial controls, onboarding, and team culture across time zones, and how you use technology to maintain accountability without a central office.

5

If youā€™ve worked with bipartisan or politically diverse stakeholders, emphasize itā€”CSI operates in red and blue states, so demonstrating neutrality and collaboration across ideological lines is a plus.

āœ‰ļø What to Emphasize in Your Cover Letter

Your cover letter should emphasize: (1) your hands-on experience building financial and administrative systems in a multi-entity nonprofit, ideally including a 501(c)(4); (2) a concrete example of scaling operations during rapid growth (e.g., new state campaigns, staff expansion) while maintaining compliance and audit readiness; (3) your ability to partner with program and executive leaders to translate strategy into budgets and forecasts; and (4) your personal commitment to criminal justice reform and how you see financial leadership as a tool for equity and impact.

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šŸ” Research Before Applying

To stand out, make sure you've researched:

  • ā†’ Study CSIā€™s legislative victories and current campaign statesā€”understand the difference between Clean Slate laws and implementation efforts, and how they affect the organizationā€™s budget and staffing needs.
  • ā†’ Research the distinction between 501(c)(3) and 501(c)(4) organizations, especially lobbying and political activity rules, since CSI operates both and youā€™ll need to ensure compliance while maximizing advocacy impact.
  • ā†’ Review CSIā€™s recent growth: the 2024 independence, 48-person staff, and expansion into the South. Look for public financials (990s, annual reports) to understand their funding sources and budget size.
  • ā†’ Learn about the broader clean slate movement, including key partners like the Clean Slate Initiativeā€™s coalition members, to speak credibly about the landscape and how finance can support advocacy.
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šŸ’¬ Prepare for These Interview Topics

Based on this role, you may be asked about:

1 How would you design a financial and administrative infrastructure for a newly independent nonprofit with a 501(c)(3) and 501(c)(4), including separate boards, shared services, and compliant cost allocation?
2 Describe your experience with fund accounting, grant compliance, and audit preparationā€”what systems and controls have you implemented to ensure clean audits across multiple entities?
3 CSI is expanding its programmatic focus from legislation to implementation, notification, and narrative change. How would you approach budgeting and forecasting for these new, sometimes unpredictable, advocacy and campaign activities?
4 How have you built and led administrative functions (HR, IT, operations) in a fully remote organization, and how do you ensure equity, transparency, and efficiency across a dispersed team?
5 Give an example of a time you identified and mitigated a significant financial or operational risk. How did you communicate it to the board and executive team, and what was the outcome?
Practice Interview Questions ā†’

āš ļø Common Mistakes to Avoid

  • Focusing only on traditional corporate finance experience without addressing nonprofit fund accounting, grant management, or multi-entity complianceā€”CSI needs someone who understands 990s, restricted funds, and board reporting.
  • Ignoring the 501(c)(4) aspect or treating it as an afterthoughtā€”this role explicitly covers both entities, and failing to discuss how youā€™d handle separate boards and lobbying rules signals a lack of preparation.
  • Presenting yourself as a purely strategic, high-level CFO without demonstrating willingness to roll up your sleevesā€”CSI is still building its infrastructure, so they need a hands-on leader who can both set strategy and execute administrative tasks.

šŸ“… Application Timeline

This position is open until filled. However, we recommend applying as soon as possible as roles at mission-driven organizations tend to fill quickly.

Typical hiring timeline:

1

Application Review

1-2 weeks

2

Initial Screening

Phone call or written assessment

3

Interviews

1-2 rounds, usually virtual

āœ“

Offer

Congratulations!

Ready to Apply?

Good luck with your application to The Clean Slate Initiative!

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