Finding Your Story: A Conversation with Jessica Siegel of Sing Creative

I first met Jessica Siegel when we were both at the Jewish United Fund. She worked on creative communications projects that made people feel something — not just words or stats on a page. Even back then, it was clear Jessica had a gift for helping organizations express their purpose in ways that inspire action.

Today, she’s the founder of Sing Creative Group, a boutique marketing and communications firm that helps nonprofits and foundations bridge the gap between good work and great storytelling. Jessica and her team partner with organizations across the country to uncover their voice, clarify their message, and connect more deeply with donors, volunteers, and the public.

As Jessica puts it, “The best marketing isn’t about being louder, it’s about being clearer and more connected.”

Over the past decade, she’s led branding, communications, and PR strategies for organizations tackling everything from education equity to reproductive justice. Her work blends strategy with empathy, helping small and mid-sized nonprofits build visibility that lasts long after a single campaign or crisis moment.

When she’s not working with clients, Jessica writes about storytelling, visibility, and the emotional side of mission-driven work. Reminding us that authenticity and strategy can (and should) coexist in a noisy world.

As impressive as starting her own business, she also co-founded North Shore Neighbors Say Bienvenidos, a group that coordinates with local neighborhoods to provide food, clothing, and shelter to asylum seekers who have been bused to the area. Jessica is a vocal advocate in her community, often speaking at local meetings about the impact of migrant arrivals and how neighbors can help.

When we sat down recently, we talked about one of our favorite topics: storytelling. Nonprofit messaging is shifting from impact reports to impact stories. As Jessica noted, “There’s nothing wrong with including some stats, but they’re far more powerful when woven into a good story.”

Beyond “We Change Lives”

If you’ve worked in nonprofit communications, you’ve probably heard the phrase “we change lives.” You’ve probably heard it a thousand times. The trick, Jessica says, is showing people how your organization changes lives. Showing what impact looks like in real life.

“You don’t want your fundraising story to sound like an academic essay,” she said. “Tell one story: how it helped one family, one person. When you say too much, people tune it out.”

Start with Listening

Nearly every project at Sing Creative begins with a messaging guide.

“We look through the lens of donors, volunteers, and prospects,” Jessica explained. “Once we understand each group, it’s easier to create design pieces and communications that connect.”

She’s also noticed a shift in how nonprofits tell their stories: “It’s less about the tearjerker videos and more about empowerment. People like to see progress, success through a journey.”

Jessica added, “We want the donor to know: this great thing happened because of your help.”

Go Through the Window, Not the Front Door

Jessica shared one of her favorite lessons from journalism school, “Go in through the window, not the front door.”

You want to nail down the specifics in storytelling; the details make people care.

“When you look through the window,” she added, “you can see the full picture:  what challenges someone faced and what it took to help them move forward. As you share that journey, you show donors both the impact of their philanthropy, and a clearer insight into the broader need.”

“Impact stats are important,” Jessica explained, “but focus on the message. Tell your story and have a call to action. You can always add, ‘For our full impact numbers, view our report.”

Keep It Short, Powerful, and Scroll-Stopping

Attention spans are short.

“People are reading this on their phones, at lunch, on a train, after a long day of work or parenting,” Jessica said. “Make it easy to read.”

That means:

●   One strong story, not several half-stories.

●   Clear, conversational language.

●   Easy to read (and listen to).

●   A call to action that’s direct and visible.

The Heart Behind the Work

When asked what drives her, Jessica smiled and answered, “I always wanted to do mission-based work. It makes me happy and proud to help organizations that do good. It’s energizing when we help a nonprofit tell their story in a more engaging way.”

Like many leaders, she’s also learned to balance ambition with sustainability. “I want to solve all the problems,” she laughed. “But I’ve learned to focus on my zone of genius and let my talented colleagues do the same. I trust them and that makes my job easier.”

Final Word

If your organization is struggling to stand out, Jessica’s advice is simple:

1. Tell one story.

2. Make it human.

3. Keep it clear.

To learn more about Jessica and Sing Creative, visit: www.singcreativegroup.com 

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I help nonprofits raise more money through education, coaching, and strategic planning. I also lead high-impact professional development, coaching programs, and retreats for companies of all sizes. If you’re ready to strengthen your fundraising strategy, turn board members into advocates, or build a comprehensive legacy giving program, let’s talk.