Welcome to Winning Thoughts, the official blog of Winning Strategy Group—we’re so glad you’re here.

Early December is often overlooked in fundraising. Most nonprofits and campaigns focus on Giving Tuesday, then save their energy for the final week of the year. But the truth is simple. Early December is one of the most strategic windows on the calendar, and the organizations that use it well consistently raise more at year end.

We are excited to announce two new partnerships that speak directly to the heart of the work we do at Winning Strategy Group: The Caldwell Institute for Public Safety and The Caldwell Foundation for Public Safety! Both founded by nationally recognized public safety advocate, commentator, and strategist Gianno Caldwell.

At Winning Strategy Group, we help clients turn the energy of Giving Tuesday into strategic momentum. Here is what you should be doing in the days immediately after.

Thanksgiving is a moment to slow down, take stock, and recognize the people who make our work possible. In fundraising and communications, we spend so much time planning, producing, and pushing that we sometimes forget the simplest truth. Generosity begins with gratitude.

Matching gifts are one of the most reliable ways to boost response and increase average gift size. When donors know their contribution will go twice as far, they feel like they are doubling their impact. It works. But like any strong tool, it can lose its power if it is used too often or without clarity.

At Winning Strategy Group, we help clients build a simple, reliable one week countdown plan. When you follow it, you decrease the stress of the day itself, increase donor engagement, and build momentum that carries you into December.

Email still raises more money than almost any other digital channel. But only when it’s done right. It’s not about sending more emails. It’s about sending the right ones, at the right time, with the right message, and the right design to make giving simple. At Winning Strategy Group, we’ve built thousands of emails across dozens of campaigns and causes. We’ve learned what gets clicks, what gets conversions, and what goes straight to trash..

If your fundraising messages go to everyone, they don’t really speak to anyone. Mass appeals are easy to send, but hard to make successful. Donors respond when your message feels like it was meant for them, not for the entire world. At Winning Strategy Group, we’ve seen what happens when clients take segmentation seriously. They raise more money, retain more donors, and build stronger long-term relationships. Here’s how to make it work.

Every campaign, every cause, every mission worth fighting for has one thing in common. A story. It’s not the spreadsheet or the slogan that moves people—it’s the emotion. Donors don’t give to organizations. They give to stories that reflect who they are and what they value. At Winning Strategy Group, we help clients build their fundraising around that truth: story first, everything else second.

here’s no faster way to reach a supporter today than through a text message.It’s immediate, personal, and nearly impossible to ignore. At Winning Strategy Group, we’ve watched SMS move from a nice-to-have tool into one of the most reliable engines for fundraising and voter engagement. Whether you’re running a campaign or raising money for a nonprofit, text messaging has become one of the most effective ways to cut through the noise and get results. Here’s how to make it wor

At Winning Strategy Group, our clients see the finished product—a polished direct mail package, a precisely targeted ad campaign, a record-breaking fundraising email. What they don’t see is the entire process that makes those wins possible.

Every fundraiser loves new donors. They’re exciting, they expand your reach, and they make the metrics look great.But here’s the truth: if you’re constantly chasing new supporters while losing the ones you already have, you’re not growing—you’re leaking. At Winning Strategy Group, we tell our clients a simple truth: donor retention beats donor acquisition every time.

As the year winds down, the pressure ramps up. For nonprofits, campaigns, and causes, the last 60 days of the year can make or break your fundraising goals. At Winning Strategy Group, we call this period the final stretch—a crucial window when smart strategy and execution can multiply results. Here’s how to capture that year-end momentum and finish strong.

At Winning Strategy Group, we’ve seen how powerful donor appreciation can be. When gratitude becomes part of your year-round communication—not just a post-donation afterthought—it transforms your fundraising results.

In a world dominated by digital screens, it’s easy to assume that traditional mail has lost its edge. But here’s the truth: direct mail remains one of the most effective tools in fundraising and marketing.

We’re thrilled to share that Winning Strategy Group is partnering with Students for Liberty on a new engagement!

Digital fundraising has changed the game for nonprofits, campaigns, and causes. With a few clicks, donors can support your mission from anywhere in the world. But while online giving is easier than ever, getting donors to take action has become harder.

One channel is never enough. Here's why multichannel campaigns work - and how you can build one that wins.

Looking ahead, here are three big trends that will define 2026—and how you can prepare now.