Job and Internship Listings

The Position

In 2023, CSI received a six-year $75 million investment through The Audacious Project, enabling significant organizational growth and a strong runway through 2028. With this foundation in place, CSI is now poised to build the next phase of its fundraising strategy, deepening major donor engagement, broadening philanthropic partnerships, and designing the infrastructure to sustain a $20 million annual budget over time.

Reporting to CEO Sheena Meade, the Chief Development Officer (or Vice President of Development, depending on experience) will co-design and lead the organization’s long-term fundraising strategy. This leader will partner closely with Sheena, an engaged fundraiser with a track record of building authentic relationships and mobilizing support, to cultivate high-impact philanthropy and expand the organization’s network of ultra-high-net-worth and institutional supporters.

The incoming CDO will have the opportunity to shape CSI’s next chapter of strategic growth, creativity, and sustainability with the opportunity to build out the development team. The Development Team currently consists of one filled Development Manager and a vacant Development Director role, plus resourcing for consultants. In addition, a portion of the organization’s Events Manager, Administrative staff and Marketing and Communications staff are allocated to support fundraising activities. Based on the direction of the organization’s fundraising strategy, additional positions may be added.

This is a unique opportunity for a few reasons:

• A strong runway and donor base: CSI has secured multi-year commitments through 2028 and an active network of ultra-high-net-worth supporters who believe in its mission.
• A CEO who fundraises: CSI’s CEO Sheena Meade is a dynamic partner with deep relationships and a clear commitment to fundraising success. Her vision is easy to connect with and inspiring.
• A chance to create and lead: As the organization’s first CDO, The new hire will co-design a fundraising strategy with the CEO, build a team, and set a course for long-term sustainability.
• A movement to believe in: The work of Clean Slate changes lives at scale and offers a unique opportunity for impact through philanthropy.

The Chief Development Officer will serve as both a strategist and lead operator, directly managing donor relationships, driving day-to-day fundraising activities, and ensuring seamless execution of all development efforts.

Strategic Fundraising Leadership

• Partner with the CEO and COO to design and implement a long-term, diversified fundraising strategy that grows operating revenue toward $20 million annually over time.
• Work closely with the CEO to engage her powerful network and strategic vision, maximizing her time with donors and ensuring coordinated follow-up and stewardship.
• Build, mentor, and lead a high-performing development team and identify future staffing and consulting needs.
• Develop a fundraising roadmap that balances major gifts, foundation support, and creative new revenue channels.

Major Donor and Institutional Engagement

• Manage and grow a portfolio of major donors and philanthropic partners, cultivating authentic relationships that reflect CSI’s values and bipartisan approach.
• Expand CSI’s ultra-high-net-worth network and introduce new donors to the movement for second chances.
• Oversee and refine the organization’s donor communications, reporting, and impact storytelling with support from the Marketing & Communications team.

Partnership and Collaboration

• Work closely with the CFO and COO to align fundraising plans with financial forecasts and organizational goals.
• Collaborate with program and campaign leaders to connect donor interests to CSI’s strategic initiatives.
• Serve as an advisor to the CEO and Board on fundraising strategy, trends, and opportunities.

Organizational Storytelling and Event

• Partner with the Marketing & Communications team to showcase CSI’s impact through events, campaigns, and public platforms.
• Develop and implement a strategy for donor and prospect engagement events (e.g., Annual Convening, Lobby Day, intimate briefings).
• Elevate the organization’s philanthropic brand as an inviting home for creative, big-thinking donors who want to change systems and lives.

The Ideal Candidate

The ideal candidate for the Chief Development Officer position possesses the following competencies:

Cross Functional Leadership: Proven ability to work across departments to leverage the CEO’s relationships and passion; ensure fundraising and program goal alignment; exceptional financial stewardship and strong donor engagement.

Fundraising Delivery: A successful track record of meeting organizational fundraising goals year over year and executing multi-year fundraising strategies. Proven experience initiating and closing seven figure gifts from major donors, philanthropic investment groups and foundations.

Creative and Sees New Ways of Doing Things: A true passion for The Clean Slate Initiative’s mission and bipartisan strategy extended to philanthropic relationships. An orientation towards authenticity and movement building over transactional relationships. Experience engaging no-partisan donors and/or donors of a diversity of political affiliations.

Commitment to Authentic and Diverse Philanthropic Relationships: Has many ideas for new ways of raising revenue that balance the organization’s financial goals and values. Sees the opportunity that CSI has in being a brand-new organization that is delivering impact at scale. Familiar with investment and outcome focused donor giving including the level of rigor in measurement, reporting, and goal setting.

Experience and Skills

• Progressive fundraising experience, including several years leading a development function and closing seven-figure gifts.
• Proven success cultivating and stewarding major donors, foundations, and philanthropic investment groups.
• Strategic thinker who can balance vision with execution and design a realistic path to growth.
• Collaborative leader who values teamwork, authentic relationship-building, and shared success.
• Experience building or scaling development infrastructure and teams.
• Familiarity with bipartisan or multi-stakeholder funding environments is a plus.

Personal Qualities

• Deep commitment to CSI’s mission and belief in the power of second chances.
• Creative and entrepreneurial mindset with a desire to build something lasting.
• Integrity, curiosity, and emotional intelligence in approach to donor relationships.
• Ability to inspire confidence and optimism through collaboration and clarity.

Who We Are

Our Commitment to Inclusion: The Clean Slate Initiative is a 501(c)(3) public entity that passes and implements laws that automatically clear eligible records for people who have completed their sentence and remained crime-free and expand who is eligible for clearance. CSI is committed to attracting, developing, and retaining exceptional people, and to creating a work environment that is dynamic, rewarding, and enables each of us to realize our potential. CSI’s work environment is safe and open to all employees and partners, respecting the full spectrum of race, color, religious creed, sex, gender identity, sexual orientation, national origin, political affiliation, ancestry, age, disability, genetic information, veteran status, and all other classifications protected by law in the locality and/or state in which you are working. Lived experience with a record, or as a family member of someone with a record, is valued.

Compensation and Benefits

Salary: The Clean Slate Initiative is committed to transparent and fair compensation. The hiring range for this position is an annual salary range of $205,000 – $215,000 per year. The final salary within this range will be determined based on work location and relevant experience. Once an offer is made, we do not negotiate the compensation package.

Benefits: Comprehensive benefits package that includes 100% employer-paid health, dental, and vision insurance, a 6% employer match towards 401k retirement, pre-tax transportation benefits, and paid holidays, vacation, sick, and volunteer time off. This is a full-time position and is considered exempt for overtime purposes. This is a remote position and we are location agnostic regarding where in the US you are based. However, we will discuss a hybrid or in-office work location for candidates in proximity to our Orlando office.

You will need to:

• ‍‍Work collaboratively with a team in various time zones.
• Be close to a major airport with the ability to travel approximately 15-20%.
• Attend required quarterly onsite planning meetings in various locations.
• Attend at least 1 staff learning trip and our annual convening each year.

Timeline and Next Steps

If you are interested in this position, please click the button at the top of the page to be directed to DRG Talent. All applicants will receive an email confirming receipt of their application.

We encourage candidates of all backgrounds to apply even if you do not meet all of the qualifications outlined above. If you are selected to move forward for an initial screening call, we expect you to hear from us by February 2026.