Jessica Cloud, Real Deal Fundraising
Jessica Cloud, CFRE, is the founder of Real Deal Fundraising. She helps nonprofit CEOs and boards raise more money and build sustainable revenue systems without exhausting their staff.
Who are you, who do you serve, and what are you focused on right now?
I'm Jessica Cloud, CFRE, founder of Real Deal Fundraising. With over 20 years of fundraising experience (mostly in higher education), I help nonprofit CEOs and boards raise more money and build sustainable revenue systems without exhausting their staff.
Most of the organizations I serve are mid-sized nonprofits with small development teams. They care deeply about their mission and have a board that wants to help with fundraising, but the structure, expectations, and strategy around fundraising are often unclear. That's where I come in.
My work focuses on helping boards and leadership teams get aligned around fundraising so it becomes a shared responsibility rather than something that quietly sits on one staff member's shoulders. Through audits, planning, and ongoing advisory support, I help organizations clarify their fundraising culture, build realistic revenue plans, and mobilize both staff and board members around relationship-based fundraising.
Right now, I'm spending a lot of time helping nonprofit leaders strengthen the governance side of fundraising and answering real-world questions from fundraisers every day. If you spend any time on TikTok, you'll probably run into me there. I regularly share short videos (@realdealfundraising) where I break down fundraising strategy, respond to nonprofit questions, and talk through the situations fundraisers face behind the scenes.
What led you into this work?
Early in my career at the University of Southern Mississippi Foundation, we brought in a consultant to develop a strategic fundraising plan for the organization. At the time, I was running the annual fund and had already built a detailed strategic plan for that program.
During the process, the consultant reviewed my work and told me it was so solid he didn't want to rewrite it. Instead, he asked to include it in his final report as an appendix, fully credited to me, so he could point to it as an example of what a clear and actionable fundraising plan looks like.
That moment stuck with me. It was the first time I realized that the skill I had developed wasn't just about managing a program. I had a knack for building strategy and presenting it in a way that made sense to leadership and could actually be put into practice.
Years later, when I started Real Deal Fundraising, I came back to that realization. Nonprofits don't just need big ideas about fundraising. They need clear plans that people can understand and use. That's the work I love doing now.
What was one of the hardest parts of building your career or business?
One of the hardest parts of building my business was trying to do it during a season of life when my time and energy were already stretched thin.
For many years I held demanding leadership roles in fundraising while raising two kids. I cared deeply about building my consulting practice, but between work and family responsibilities it was difficult to give it consistent attention. I would write, teach, and market for a while, then burnout would creep in and I'd step away. Opportunities still came in from time to time, but each time I returned to it, I felt like I was starting from scratch.
Over time I realized two things. First, seasons matter. My kids are older now and much more independent, which has opened up space to invest more consistently in my work. Second, I've learned how to work smarter. I batch content, automate parts of my marketing, and build systems that allow the business to keep moving forward without requiring constant effort.
Burnout taught me something valuable. A sustainable career or business is built through systems and patience, not just effort.
What's a project you're proud of?
A large comprehensive university was seriously considering shutting down their student calling program. The program had generated less than $50,000 in trackable gifts, and the internal processes were working against them. When I reviewed their systems, I discovered their credit card process required nineteen separate steps for a donor to complete a gift.
Instead of recommending they abandon the program, I helped them rethink the infrastructure behind it. We identified new technology that simplified the giving process and made it much easier for donors to complete gifts during calls.
Credit card gifts rose to more than 36 percent of all pledges. The average gift increased from about $85 to over $125. And the program went from five-figure returns to more than $394,000 pledged in a single year.
That project is a great reminder that fundraising problems are often system problems.
What are you building right now?
I'm refining the core consulting services I offer to nonprofit leaders and boards around a clear progression that helps organizations move from confusion to coordinated action. It starts with evaluating how the board and leadership team currently approach fundraising, then moves into facilitated planning that aligns everyone around realistic goals and clear responsibilities. From there, I often stay involved as an advisor while they implement the plan so the momentum doesn't fade.
I'm also growing the content side of my work. My newsletter, articles, and daily videos let nonprofit leaders learn from me long before they ever become clients.
What belief about consulting or nonprofit work has changed for you?
Early in my career, I absorbed a belief that is pretty common in nonprofit work: that caring about the mission means you should be willing to sacrifice your time, your energy, and sometimes even your well-being.
Over time, I saw talented fundraisers burning out and leaving the field. I saw organizations struggle with turnover and instability. It became clear that sacrificing people in the name of the mission doesn't actually serve the mission at all.
Now I believe strong fundraising programs are built on sustainable systems, clear strategy, and leadership that respects the people doing the work. When organizations take that approach, they raise more money and keep talented professionals in the field longer.
What advice would you give someone earlier in their journey?
Go ahead and choose a niche.
Spend some time figuring out what part of the work genuinely energizes you: the conversations you enjoy having and the problems you like solving. Then build your messaging around that.
For a long time, I believed that since I had experience across so many areas of fundraising, I should showcase all of it. The result was messaging that felt scattered. When you try to speak to everyone, people struggle to understand exactly how you help.
Once you narrow your focus, your message becomes clearer and the right people start recognizing themselves in what you're describing. And here's the secret: choosing a niche in your marketing doesn't mean you'll never do anything else. Opportunities from your network will still appear. The difference is that people will know exactly why they should come to you in the first place.