A Framework for Communications and Fundraising Collaboration: PLAN™

By Olga Moshinsky Woltman

It’s not uncommon for communications and fundraising functions to report to separate departments. While it may seem logical on paper, this setup sometimes hinders collaboration. Competing priorities, lack of understanding and benign neglect can get in the way.

Without a deeper understanding of fundraising and direct response fundamentals, communicators generally focus on broad awareness and prioritize organizational wins over unmet needs. It is not uncommon for fundraisers to undervalue the strategic role of communications, treating it as a short-order cook rather than a partner in driving engagement and revenue. Occasionally, there’s also a subtle resentment that communications and marketing functions do not bear the same pressure of direct revenue goals.

There is much to be gained by bridging this gap between these core functions. When communications and fundraising operate in lockstep, beyond mere cooperation, they complement each other and drive greater impact. Building a genuine partnership requires a sustained and deliberate effort rooted in goodwill, empathy and shared goals.

Introducing PLAN™ Collaboration Framework

Changing organizational structure to bring communications and fundraising into a single team can help bridge the gaps, but these types of shifts can be disruptive, impractical and sometimes unwise. A more collaborative approach can achieve the same goal. Having been both a fundraiser and a communicator, I’ve experienced firsthand the challenges and tensions that arise between these teams. Stepping back as a consultant has given me an even broader perspective on what helps them work better together.

Drawing on these experiences, I developed the PLAN™ framework to strengthen collaboration, align efforts and ensure both teams support each other’s needs.

The PLAN™ framework is built around four key elements: partnership, leadership, alignment and narrative. The framework is not a one-and-done checklist, but a wholistic and ongoing commitment to collaboration. With all four elements in place, both teams are better equipped to support each other, strengthen their results and, ultimately, advance the organization’s mission. Even with three of the four elements in place, it is possible to significantly improve collaboration.

Partnership: Setting Intention

The foundation of collaboration is the explicit choice to work together by coming to the table with empathy and an open heart for the greater good. True partnership is built on trust, open communication and chemistry. The key to success is to involve the right people — individuals who are secure in their respective expertise and genuinely committed to working together.

Partnership isn’t about checking a box. It is about willingness to work together from start to finish, from budgeting and goal-setting to planning and ideation to execution and evaluating results.

Marketing and communications teams should be brought in early to help shape strategies and decisions rather than just executing tasks. Understanding and involvement provides context and buy-in that allows communications teams to craft messages and develop materials that resonate with donor motivations. At the same time, transparently sharing fundraising goals gives everyone on the team a sense of ownership.

In true partnerships, successes are shared, and failures are collective. It’s important to come together to debrief and assess what worked, what didn’t, and how to refine strategies for future success.

Don’t neglect partners and agencies. It is also important to involve external partners in this process to set the tone to work as a unified unit.

Leadership: Setting the Tone

Collaboration doesn’t just happen. It’s shaped by leadership. When leaders actively prioritize teamwork between marketing and communications and fundraising, it sets the tone and shifts the culture from working in silos to working in sync. This isn’t about mandating that teams play nice, it’s about showing through actions that working together creates better results.

Strong leadership means modeling collaboration in action, breaking down silos, encouraging open dialogue and making sure both teams feel valued. Leaders should help teams envision a better way of working, step in when things go off track and celebrate shared wins. This commitment has to be authentic. Nothing erodes trust faster than empty gestures and lip service.

At its core, leadership is about creating an environment where communications and fundraising see each other as partners, not obstacles. To reinforce this, leaders can facilitate joint planning, set shared goals and ensure regular touch points between teams. When that happens, everything else falls into place — whether it is strategy, execution or impact.

Alignment: Taking Practical Steps

Alignment is a nice idea, but it requires infrastructure to put it from theory into action. It’s the operational layer that ensures teams aren’t just aware of each other’s work but actively working together. Without these processes and built-in ways of doing the work, over time good intentions can fizzle out.

The best part? This is where anyone — regardless of their role on the team — has the opportunity to make small changes and improvements that signal your commitment. These may be just the nudge others need to begin contributing to smoother operations and stronger collaboration.

Transparency and open access are key. Gatekeeping behaviors creates bottlenecks and undercut trust, making it harder to get things done. The goal isn’t just to communicate but to build habits and muscle memory that keep everyone on the same page. Here are some practical ways to make alignment part of the day-to-day:

• Joint planning sessions. Holding quarterly and campaign-specific planning sessions helps teams align on goals, strategies and timelines before work begins.
• Regular check-ins. Scheduled and ad hoc conversations at all levels keep teams connected and prevent small issues from becoming big problems. These day-to-day interactions also help build bonds and trust.
• Standardized processes. Clear, documented workflows set expectations, so no one is left guessing about roles or deadlines.
• Visibility into deliverables. When teams understand what’s coming and when — without having to awkwardly ask about status yet again — it cuts down on frustration and last-minute scrambles.
• Shared calendars and timelines. A common view of key dates and campaigns helps everyone plan ahead and spot potential conflicts early.
• Collaborative editorial planning. It’s important for communications teams to invite input from fundraising and other departments to ensure messaging aligns with broader goals.
• Content and template libraries. A shared resource hub with stories, metrics, templates and testimonials makes it easier to create consistent, high-quality materials.
• Dashboards and metrics. Tracking performance together ensures both teams are working toward the same key performance indicators and measuring what matters.
• Feedback loops. Campaign post-mortems are a chance to assess what worked, what didn’t and what to tweak next time.

These aren’t just best practices — they’re the foundation of a smoother, more effective collaboration that makes everyone’s job easier.

Narrative: Creating a Unified Approach

The narrative is where everything comes together. Isn’t this why we set out to build collaboration between communications and fundraising in the first place? Organizational narrative is where all of these efforts come together to craft the story of the organization, aligned with various goals and balancing messaging about the need for ongoing support and the tangible impact that donations make.

The “what" and “when" of planning are the easy parts. Starting with the audience in mind is the important part. Understand their needs and motivations, and define objectives for each segment. In other words, what are we trying to accomplish? By considering the audience first, teams can shape messaging that speaks directly to their motivations, guiding them toward the desired actions. These decisions will drive the organization’s overarching story.

It’s also crucial to consider the channels you’re using. What works, which channels and platforms does the audience use and how do they engage with them? The same person reading an email engages differently than they do on social media.

Spoiler: Not everything translates well across all channels. You may decide that some channels do not serve a purpose at all and do not offer you value. It’s important to identify these issues early and reallocate precious resources.

Lastly, how do you know all of these efforts are working? Well, data is your guide. Using data to measure performance and track results helps you continuously optimize your efforts. Data does not pick sides. It’s there to help guide decisions and refine your approach.

The takeaway here is not just what you include in the narrative, but the fact that planning is done collaboratively with different perspectives around the table.

Turning Ideas Into Action

The PLAN™ framework is just a starting point, not a one-and-done checklist. Think of it as a living, breathing guide to building stronger collaboration between communications and fundraising. It’s about creating systems that, over time, become ingrained in the daily rhythm of work. Achieving all elements right away isn’t the goal. Any step forward that moves teams toward greater collaboration is progress. Sometimes change happens quickly, alongside other organizational shifts, and sometimes it’s gradual.

Take the PLAN™ framework and make it your own. Start small, make adjustments where you can, and keep pushing for improvement. Your partnership isn’t just a nice-to-have — it’s essential to unlocking the full potential of your mission.

Olga Moshinsky Woltman is widely recognized in the nonprofit sector for expertise in communications, fundraising and organizational strategy. A frequent contributor to industry podcasts and publications, and host of the People of Substance by LemonSkies podcast, Olga also serves on several nonprofit boards. She can be reached at owoltman@lemon-skies.com.

Your End-of-Year Campaign Starts Now: The Importance of Starting Your Planning Early

By Alyssa Ackerman

While the end of the year may feel far away, those behind the most successful fundraising programs are already planning for year end. Strategic planning now can have a lasting impact on your campaign performance come December when stakes are high and opportunities are plentiful.

The months leading up to the end of the year are critical for testing, acquisition and preparing the core elements of your campaign. This is the time to focus on bold testing strategies, building your audience and laying the groundwork for any tactics that require a longer lead time.

Bold Testing Strategies

By the time year-end fundraising season arrives, your donation forms, calls to action and creative assets should be fully optimized. This doesn’t mean you can’t test in December, but it does mean you should avoid high-risk tests during a period when performance matters most. Instead, develop a structured testing calendar now to ensure that only top-performing strategies make it into your year-end campaign.

Identifying which key metrics need improvement is essential to developing the most effective testing plan. Have you noticed a decline in your average gift? Testing different ask strings might help lift performance without decreasing your conversion rate. Or perhaps your page completion rate has dropped. This could signal it’s time for a complete redesign (if you want to go big) or incremental changes to your donation form to increase page completion rate. By evaluating the trends you’re seeing in your key performance indicators prior to giving season, you can test your way to the most optimal performance come December.

Building Your Audience

Another area of focus as you begin to plan, should be acquisition. At MissionWired, for example, we’ve seen investments in audience growth help organizations scale up during the end of year — but not only at the end of the year, for the long term. Several members of our digital co-op who invested to grow their audiences ahead of December, saw significant payoff during year-end fundraising, with some members seeing more than 40% of their email revenue come from co-op delivered leads.

Continuing to acquire new, low-dollar donors and mid-level prospects is critical to the long-term health of your program. There are audiences that you’re not yet connecting with and people with an interest in your work you’re not yet asking to support your cause. By investing consistently in acquisition, you can keep the door open to find and engage the supporters who will become your next sustainers and mid-level donors. And these investments pay off massively in key moments like end of year.

Laying the Groundwork

Some of the most effective end-of-year fundraising tactics require advance planning, so it’s essential to start laying the groundwork now. If your program is feeling the effects of crowded inboxes, and you’re exploring ways to diversify your outreach through paid media or SMS, those efforts should begin well before December. Channel diversification takes time to plan, test and implement effectively.

Similarly, if you’re hoping to secure a matching gift for your campaign, now is the time to pitch the idea internally and identify potential partners or funders. Whether you’re aiming for a specific match amount or a compelling donor incentive, early alignment with stakeholders is key to making it happen.

Planning to include video content or enlist a celebrity supporter? These are powerful strategies that can elevate your campaign but they come with longer timelines for coordination, production and approval. Start pitching these ideas and moving them through your internal processes now to ensure they’re ready to go when it matters most.

The Bottom Line

Your end-of-year campaign doesn’t start in December — it starts now. With smart testing, intentional acquisition and early planning, you’ll set yourself up for a record-breaking season and long-term fundraising success!

As vice president at MissionWired, Alyssa Ackerman partners with nonprofit partners to drive donor engagement and fundraising growth through direct response. She can be reached at alyssa.ackerman@missionwired.com.

How Can Your Tech Stack Support Omnichannel Marketing? Omnichannel Marketing, Building Blocks and Challenges

By Sally Heaven and Charlotte Kresse

Omnichannel marketing is the goal for nonprofits when deciding the best form of communication with supporters. So, how do we get there?

What is Omnichannel Marketing?

“Omnichannel” is a term that you’ve probably heard a lot. To make sure we’re all starting from the same place, let’s define it.

Omnichannel marketing creates a seamless, consistent experience for your supporters across every engagement channel. We’re talking online and offline, email and direct mail, SMS (text), social media, telemarketing, events, the website — the whole nine yards.

Imagine your supporter reads an email from you, views a Facebook post, opens up a letter and talks on the phone to a fundraiser. Regardless of what they read, hear or see, the message is consistent and cohesive. Your supporter always knows “Hey, it’s that organization that does great work!" They never feel like “Wow, this letter sounds like it was written by a totally different person than the email I saw earlier .”

What Are the Building Blocks?

It’s easy to describe what omnichannel marketing is. But achieving it isn’t always simple. Let’s peel back the layers and see what goes into creating a truly omnichannel experience.

A clear journey. The messaging for omnichannel should meet your supporters where they are. If a person is brand new to your organization, the messaging they see should reflect that they’re new with a welcome, and should invite them to make a gift as one of their first actions! But if your supporter has been a longtime subscriber and donor, you should communicate a different message that takes into account what they’ve done in the past.

It requires data. Your organization probably uses a variety of software solutions that make up your tech stack to segment direct mail, create call lists, target your email and time a text message to arrive at the right time. That means getting the data from point A (the engagement channel solution) to point B (a centralized location where it can intermingle with data from other channels), and then back out to points C, D and E to get the right message (other engagement channels).

The next best action. Have you ever visited a store’s website to browse products and then immediately received an email or a text inviting you to come back and make a purchase? You can bet that the store knows who you are, their central location for data knew you came to the website, and their journey for you said “Send that person an email now!" These are called event-based triggers for marketing.

Consistent messaging. Your organization has a mission and a voice. Every program should reflect that voice, but it requires commitment and oversight from someone in charge of the brand — especially if your messaging is currently fragmented. For example, if it’s easy to tell whether the development or political department wrote an email, turning this ship around will take time and attention.

Omnichannel marketing creates a seamless, consistent experience for your supporters across every engagement channel.

Why Is This Challenging?

Seeing what goes into an omnichannel marketing strategy can help us understand why it’s not simply as easy as snapping our fingers and saying “Poof! We’re omnichannel.” Here are some technical reasons why organizations might be struggling to implement omnichannel.

Their existing technology doesn’t support it. Some organizations have a donor database that is really good at managing their donors. Some organizations have a constituent relationship management solution that manages all supporters and subscribers. In the last couple of decades, we’ve seen organizations try to cram all of their data from all their diverse channels into one relational database as that central location. It doesn’t always work, because the custom fields might be limited or the data model might not support it.

Data schemas are different. A database tool accepts data in tables, called a “schema,” and they have definitions around format. Here’s a simple example: Sometimes the same field in different tools isn’t formatted the same way. A phone number in one database might be formatted as “(555) 555-1212” while “5555551212” in another system. Even though these are both phone numbers, you might need to transform the data from one system to another so the tool can understand it.

Data integration can be a heavy lift. Data integration is complex. In order to know whether Jane Smith in one system is the same Jane Smith in another system, nonprofits need to know that these Jane Smiths are the same person, but this other Jane Smith is not that Jane Smith. And let’s not even start talking about duplicates.

Organizational culture and resistance to change. Going from “the way we’ve always done it" to “something new" is hard. Change is difficult. Moving to omnichannel needs a patient, wise and process-oriented champion with enough organizational leadership experience to keep everyone going even when the going gets tough.

Now we know true omnichannel marketing is complex and can be challenging. How do we get started? In part two of this series, “How Can Your Tech Stack Support Omnichannel Marketing? — Solutions to Power Your Omnichannel Marketing,” we’ll talk about solutions — all the way from free and do-it-yourself to not free but incredibly powerful and built for purpose.

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Part2: Let’s Talk Solutions to Power Your Omnichannel Marketing

We previously told you about “Point B”— centralized location for your supporter data where it can intermingle with your other data, become improved with more knowledge, and then trigger the best next message and action for that supporter.

What is that centralized location? Here’s where it gets fun. These solutions require that your organization spends time thinking about your supporters, what kind of journey you want them to have when they join your organization, and what messages and touchpoints are included for each campaign. This is usually the job of a dedicated marketing individual or team.

1. Spreadsheets. Everyone’s favorite data centralization tool is spreadsheets! The most common are Microsoft Excel and Google Sheets. If you don’t have a data analysis, visualization, and segmentation solution as part of your organization’s technology stack, you can absolutely get started by using spreadsheets to consolidate data from different systems, map it, and connect it by using pivot tables and charts. Then you take the segments you create and use them for your emails, texts, phone calls, and mail.

Pros: Your organization already has spreadsheets, so this solution doesn’t cost additional money. (It does take up a lot of staff time and you need someone who is an expert at spreadsheet formulas.)

Cons: You will have to create every connection between data yourself, and continually refresh your spreadsheets. If you have extremely complex operations, this solution probably won’t work for you. Most likely, a small number of people can actually do this, so reports can’t be generated on demand by just anyone. You will also need to manually export the segments you create and push them into your engagement tools.

2. Your existing donor database or CRM. We did say these aren’t always the best tools for bringing together data from different systems in an easy or seamless way, but it can be done to some extent. If there’s no room in your budget this year to buy new tech, then you can use the custom fields, attributes, and codes in your existing database to accommodate the types of data you want to analyze and use the existing segmentation or query tool.

Pros: It’s tech you already own, and you probably have some people on your staff who are experts at using the database or CRM. With some thoughtful solution design, you can probably uncover some insights that might otherwise have eluded you. If your database or CRM is integrated with your engagement tools, you might be able to push those segments into your email, SMS, and other tools fairly easily.

Cons: Some databases have limited numbers of fields and codes available. Some have unlimited numbers. Either way, you’ll be creating many more visible codes in your system that may not be core to its function of managing donor data, so things could get cluttered. Also, your database team may only have limited time to help solution design and manage the additional requests. Finally, if your database or CRM is not integrated with your engagement tools, you’ll need to get the segments in there manually.

3. Build your own new database. I know, this sounds like a lot! But these days there are many cloud-based tools that look like the spreadsheets we all know and love, but actually allow you to create real, relational databases and manage workflows. It’s not a full-fledged visualization platform, but some cloud-based solutions like Airtable, Smartsheet, Notion, or Quickbase, which are best known for their project management chops, can absolutely be designed to help analyze data in a central location. These solutions do cost money to manage larger amounts of data, but usually not a whopping amount.

Pros: A cloud-based solution that is truly relational allows for a lot of flexibility in designing the solution. Some products include AI features to help you with your build or data analysis. A cloud-based solution also scales more easily than regular spreadsheets. You might be able to integrate this system with your engagement tools to transfer segments.

Cons: The tech savvy and learning curve to construct a working tool from these products is fairly high. It’s probably not something people on your staff without prior experience in this area can casually pick up. You will also need to evaluate the security of a cloud-based solution if you intend to bring into it Personally Identifiable Information (PII). And if you can’t integrate with your engagement tools, you’ll need to manually transfer segments there.

Data security and privacy: Anytime you bring a new tool into your technology stack, you’ll need to make sure that the solution complies with data privacy and security standards and requirements. This work has likely already been accomplished for your in-house business applications and your donor database or CRM. If you purchase a new cloud-based data solution, it’s on you to make sure it’s up to your security standards.

4. Your agency: Your direct response agency most likely has a lot of knowledge about bringing data together, gleaning insights, performing segmentation, and presenting information in an understandable and actionable way. It’s part of the core service they provide to you when managing your direct response activities. Many agencies have built their own segmentation tools, or customized a commercially available tool in order to serve their clients. It’s worth describing what you want to do and seeing if they can provide it.

Pros: Your existing relationship with an agency and the trust you already have in them with your data is valuable. Agencies are great at communicating and listening to clients to figure out what they need and whether they can help. Plus, they might already have a process or an integration built to your engagement tools.

Cons: Depending on what type of tools your agency has in-house, they might not be able to accommodate every use case you’re looking for. And if you have data scientists on your team, they might prefer tools they can manage directly.

5. Data Warehouse, Data Lake, Data Lakehouse, Visualization Platforms. So much data, so many places to store it!

• A data warehouse is, in essence, a giant and powerful database where all data that comes into it is “structured" — that is, the data exists in rows and columns, it is defined, transformed if necessary, and matched up to other data, so we know THIS Jane Smith from email is the same as THAT Jane Smith from direct mail.
• A data lake can contain all kinds of data: structured, unstructured, text documents, video, web logs, the whole nine yards. Sounds messy, right? It is, but the great thing about a data lake is that if you use a data lakehouse you can use AI to analyze the data and draw conclusions and make models from it.
• A data lakehouse is like a data warehouse, but it can also connect to and use the data in a data lake. You get the best of both worlds.
• A visualization platform lets you construct charts, graphs, dashboards, and other types of visualizations of the data that’s contained in a lakehouse or warehouse. It’s like “Create Chart" in Excel, except with realllllly big data sets.

Pros: Powerful data storage and visualization capabilities. The ability to slice and dice large data sets and render them instantly visible in graphs, charts, and other artifacts that illustrate points and insights about your data. Compatibility with your engagement tools is a requirement to look into, as well.

Cons: You’ll need significant budget for this, both to pay for software and for an expert to help you set it up. You’ll also need someone on your staff with skills to maintain and manage the stack, and to create new views.

6. A Customer Data Platform. A Customer Data Platform (CDP) for marketing is the pinnacle of omnichannel marketing. A CDP is a product designed to help nonprofits unify supporter data across all channels. A marketing CDP can trigger the next right action for each specific supporter according to the customer journey and defined campaigns. The CDP accomplishes this mission statement of omnichannel: “Send the right message to the right person at the right time .”

Pros: Your CDP can leverage automation, machine learning, artificial intelligence, and all the latest tools to make sure the right actions happen at the right time and to the right people. With built-in learning and more data, your CDP will get better over time.

Cons: It takes time and expertise to work alongside experts to configure a CDP, imagine the journeys, and create campaigns. And of course, a CDP costs money, so you’ll need to budget for it. Moving to a full-fledged CDP can cause resistance because change is hard.

Change Management: For any change to process, technology, or both, managing the change and its impact on your people is important to ensure a successful project. Implementing a CDP requires careful planning and attention to how your staff will experience this change. Your leadership and commitment will be key factors for success.

Sally Heaven is co-founder of Raise HECK. After spending seven years working at a nonprofit in online advocacy and 13 years in built-for-purpose nonprofit software, she co-founded Raise HECK to help organizations choose and use the best technology to fit their missions. Reach Sally by email at sally@raiseheck.com.

Charlotte Kresse is also co-founder of Raise HECK. She has worked on Capitol Hill, at a national nonprofit supporting affiliates’ digital marketing, a direct response agency, a software company and then co-founded Raise HECK to bring her diverse experience directly to organizations to help them maximize their solutions. You can contact Charlotte by email at charlotte@raiseheck.com.

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Ignite Fundraising Results with AI

Nonprofits are being asked to do more with less. Whether you’re managing national campaigns or regional donor outreach, the challenges are the same: reach the right people, on the right channels, with the right message while keeping costs down and maximizing returns. At the same time, donor expectations are rising. Donors want relevance, expect personalization, and respond to authenticity not marketing.

AI enables a new operating model for fundraising, one that automates what’s manual, simplifies what’s complex, and accelerates every stage of campaign execution. This isn’t just about working faster, it’s about transforming how fundraising gets done. According to Forrester, agencies using AI reduce time to market by over 80% and cut production costs in half. Global brands deploying AI at scale see up to 70% better performance. That kind of lift isn’t theoretical, it’s real, and here for nonprofits.

SMARTER ENGAGEMENT. LESS WASTE. BETTER RESULTS.

AI-powered fundraising starts before a campaign ever launches. Predictive models assess your donor file, scoring individuals based on behavior, recency, frequency, and capacity so you focus only on those with the highest likelihood to act.

Use cases include:

• Identifying the top 10% of prospects most likely to donate in an upcoming campaign.
• Flagging loyal donors at risk of lapsing, so you can intervene early.
• Re-ranking lapsed names to prioritize those with the best reactivation scores.

In practice, we helped a major healthcare nonprofit reduce acquisition costs by 7% by removing unlikely responders from their mail plan. Another organization used machine learning to shift focus toward monthly givers, increasing net revenue by 9% without increasing spend. The lesson? Smarter decisions driven by AI consistently outperform “what worked last year .”

PERSONALIZATION THAT SCALES

Fundraising personalization used to mean dozens of creative versions, complex A/B testing, and high-pressure production timelines. Now, generative AI automates the creation of tailored content freeing your team to focus on strategy, not spreadsheets.

AI lets you:

• Generate copy for any channel that is aligned to each donor’s motivation: impact, community, recognition, urgency.
• Automatically follow up on donor interactions, such as thank-you letters and tax receipts, in the right tones or languages.
• Rapidly develop multiple variations of subject lines, calls-to-action, and message models to determine what creates the most engagement and results.

This isn’t hypothetical. Our clients are already using generative AI to deliver dynamic copy at scale. Messages sound more personal because they are. And the results speak for themselves:

• 20% reduction in acquisition costs, on average.
• 30% lift in net revenue across multiple campaigns.
• Up to 100% improvement in reactivation ROI using AI-generated targeting and creativity.

AUTOMATED CHANNEL STRATEGY

Another advantage of AI? It automates which donors are contacted and how. Instead of generic segmentation rules or rigid cadence charts, AI models adapt to live performance data. They recommend:

• Which donors should receive print vs. digital.
• Who should get both and when.
• When to suppress names to avoid fatigue or wasted cost.

In one case, a nonprofit eliminated nearly 50% of underperforming names in their digital campaign by replacing them with reactivation candidates selected by AI with no increase in budget. The results? Higher conversion, stronger ROI, and lower per-donor cost.

That’s the future of campaign orchestration: smart, adaptive, and automated.

AI-POWERED FUNDRAISING DIFFERENTIATION

To win today, nonprofits must go beyond tactical applications. AI isn’t a feature, it’s a foundation. And transforming fundraising outcomes means embedding AI into five key areas:

1. Human Review of AI-Generated Content Fundraisers guide, approve, and refine AI outputs so the brand stays intact and the voice stays genuine.
2. Hyper-Segmentation via ML & AI Create dynamic audiences that update automatically based on behavior, giving history, and predictive scores.
3. Data Enrichment for Modeling Combine your CRM with external data, commercial overlays, modeled demographics, and intent signals to sharpen audience insights.
4. Automated Premiums and Fulfillment Link AI-based segmentation to backend systems for personalized incentives across print and digital with fulfillment handled automatically.
5. End-to-End Print + Digital Integration Coordinate your multichannel programs with precision so that the message, creative, and channel aligns to donor preference and delivers performance.

This is how leading nonprofits are unlocking higher performance with AI.

TAKE THE NEXT STEP

AI fundraising isn’t just possible. It’s already being deployed by health, environmental, humanitarian, animal welfare, and advocacy organizations today. The results are measurable. The process is proven. And the opportunity is now. At Market Holdings, our agency brands are applying AI across hundreds of campaigns. From building smarter models to generating creative content to managing complex print and digital workflows we’ve automated the hard parts so you can scale what works.

Let’s talk about how we can do the same for you.

Fundraising AI isn’t coming. It’s here. Let’s use it to grow your mission.

Fundraising AI isn’t coming IT IS HERE.

Let’s use it together to power your mission forward.

Pushing the Envelope: Team Brainstorming Works

By Steve Fleshman

Trying to beat your control? Need some inspiration for a new appeal or acquisition package? Here is something I’ve been doing with my clients — both internal and external — for many years.

What I call “pushing the envelope" is a group brainstorm focused on generating ideas without judgment. The goal isn’t to find the perfect solution — it’s to spark as many ideas as possible and build on the best ones.

At its best, it’s collaborative, fast-paced and full of unexpected breakthroughs. At its worst, it’s a fun collaboration and a team-building exercise.

Everyone sees the world differently. A mix of backgrounds and job roles brings fresh angles to familiar problems.

There isn’t a monopoly on good ideas. Someone says “turquoise envelope" or tosses out a half-formed thought. Another person builds on it and then someone else adds another. That’s where the magic happens.

When I worked at a large credit card company, our team receptionist came up with the best package, which became a winning control.

And when a group helps shape a solution, the entire team is more likely to support it and help bring it to life. Brainstorming can break the ice and help people feel more comfortable speaking up in the future.

Who Should Be in the Brainstorm Session?

The ideal group size is four to eight people, but anyone could be a vital part of the session.

Not sure who to invite? Use this quick checklist as a guide:

• Different departments. Variety equals better input. Just be sure to avoid jargon and acronyms, as those unfamiliar with direct mail lingo may feel confused and clam up because they don’t know the meaning of a Johnson Box or a CTA.
• People close to the problem. They see what others don’t.
• A fresh pair of eyes. Outsiders often ask the smartest questions.
• Creative thinkers. Energy-boosters think outside of the box.
• The scribe. Personally I like this to be a graphic designer, but don’t let them draw anything at this point. If they are like me, they’re losing in Pictionary because they’re drawing a perfect coffee cup while the other team has already yelled out “coffee break .”
• A facilitator. Someone to guide the session and keep it balanced.

Tips for a Productive Session

Carbohydrates are key. Provide drinks and snacks, keeping all dietary restrictions in mind.

Begin with a few warmup exercises. Consider brainteasers to break the ice.

Start with a clear goal. What problem are you solving? I find a simple creative brief helps everyone focus. Keep it simple but concise. That’s your North Star.

Create a judgment-free zone. No idea is too out there. The weirder, the better — at least to start. The Talon zipper company of Meadville, Pennsylvania, held a brainstorming exercise to try to find new uses for their product. The session was going nowhere until one participant said, “I think we should build a zipper to the moon .” That set the mood for creative ideas, and no one thought their idea would be ridiculed.

Use a structure. Have everyone call out their idea, write it on a sticky note and place it on the wall, or go around a circle so everyone contributes.

Keep it short. Between 30 and 60 minutes is usually enough. Shorter sessions keep energy levels high.

Capture every idea. Use a whiteboard, doc or someone’s phone to track everything. You never know what will click later.

Sketch a final idea. At this point, your graphic designer can be put to work thumbnailing your top solution package. I’m not talking about that perfect envelope, but something representational of the full packages.

Follow up. After the session, narrow down the ideas and keep the team in the loop on next steps.

Common Pitfalls to Avoid

Try to avoid letting one or two people dominate the conversation. Keep the session balanced. Ask quieter team members directly for input if needed.

If criticism creeps in, shut down judging early. Idea-vetting comes after brainstorming, not during. But be careful, because this can cause the critical person to shut down if you make them a pariah.

Don’t just talk. Have a clear direction; a clear question or goal gives the session structure and purpose.

Pushing the envelope is more than a meeting — it’s a space where creativity thrives and collaboration shines. When done well, it’s a low-pressure way to bring out the best in your team.

So next time you hit a wall, don’t try to push through it alone. Get a few people together, ask the right questions and let the ideas flow.

You might be surprised by what you come up with — together.

Steve Fleshman is founder and creative partner of DR2. If you want to know the solutions to the warmup exercises or talk brainstorming, he can be reached at steve@dr-2.com.

Digital Exclusive

Your Data Deserves an Annual Check-Up

By Anne Paschkopić

Every year, I go into my doctor’s office for my annual physical. It’s not a particularly exciting or enjoyable experience, but I do it anyway because I know it’s important for my health.

Here’s my pitch: why not do the same thing for your email data?

Whether you’re a small organization doing the most with the least, a large group with complex, intricate interconnected systems, or somewhere in-between, everyone can benefit from taking the occasional step back to check whether everything is in order.

Like any good doctor’s visit, your data check-up should cover three main areas:

Vital Signs

Focus on the parts of your program that may be overlooked most of the time. These often fall into one of two categories. First, the ones you use every day and so might not notice gradual changes over time. Two, those that were set up so long ago that you assume they’re working… but are they?

• Audience criteria: Take a deep dive into the queries, lists, searches, or data extensions that you use to target, suppress, and define your email audiences.
  • Look at each piece of logic with a skeptical eye: does this really mean what I think it does?
  • Leave no stone unturned: if your audience has nested queries, or relies on data points synced from another system, check those too.
• Automations: I too have been guilty of saying “set ’em and forget ’em!" but in truth, automations should never be forgotten. Check that they’re still running smoothly by checking:
  • Are the right supporters are entering?
  • Are they moving through choice points correctly?
  • Are they exiting as planned — and in the right volume?
• Consent: Check your opt-in process:
  • Iis it implemented correctly?
  • Across different types of pages…
  • and data streams?
  • Can someone who opted out opt back in, and vice versa?
• Look at the missing pieces. Looking at what’s not there can sometimes reveal missing pieces that would otherwise go unnoticed.
  • Who isn’t receiving emails?
  • Who joined without a welcome series, or lapsed without going through the renewal automation?
  • Who’s opted out…or has no status at all?

Sore Spots

Do you have a sneaking suspicion you have more donors than are captured in your “Active Donor" group? Is your post-action donation conversion rate way below M+R’s benchmark for your sector and you have no idea why? Does it feel like your advocacy action going viral last month should’ve translated to way more new email sign-ups?

Now’s the time to take a closer look at those little problems that never rose to the level of immediate urgency, that you’ve been meaning to check into but never got around to, and to follow up on your hunches.

Recovery Plan

Work with your colleagues to correct (and test!) any logic errors you found. Consult your CRM’s support staff to understand and address any unexpected behavior.

If you discovered a pocket of subscribers who should be getting emails, but aren’t, make a careful plan to reincorporate them into your email list without risking deliverability. If that group is particularly large (more than 10% of your list size), particularly old (a year or more without an email), or both, consider using M+R’s Scout Quest data co-op to identify who on your list is still active with other nonprofits — and who’s not worth the risk.

While you’re at it, this is a great time to archive anything you’re not using: outdated email templates, old prospect lists, last year’s donation pages. (Just make sure those pages redirect to a live page somewhere!) It’s also a good opportunity to update (or create!) internal documentation.

And then, make an appointment with yourself in 2026 — for next year’s data check-up!

Anne Paschkopić is the Managing Production Specialist at M+R, where she fluently translates between strategy and CRM, demystifies deliverability, and heads up a production team capable of implementing the most complex multi-variant multi-channel campaign. When she’s not communing with Asana, she spends her free time knitting, petting cats, and watching women’s sports.

Digital Exclusive

Bridging the Gap with CARE: Staffing Strategies to Unify Fundraising & Tech Teams

By Justin Birdsong

The modern nonprofit fundraising apparatus, particularly in direct response, relies on rich, actionable data on donors and prospects that support intelligent, responsive segmentation, messaging tailored to donor expectations and interests, and carefully crafted donor experiences. Yet in conversations with nonprofit colleagues and clients, nearly all point to a disconnect between their fundraising teams and marketing technology/donor database teams as one of their most significant pain points.

When I tell the story of Skeleton Key’s consulting work, I find that what clients initially describe as a technology problem almost never turns out to be about technology at all. What we uncover beneath an organization’s self-described tech woes are usually interpersonal issues, where gaps or breakdowns in structure and process play out in human dynamics between teams. Whether about redefining ways of working (decision making, governance, collaboration) or navigating tensions inherent in managing cross-functional technology ecosystems (ownership, prioritization, strategic alignment), a CRM transformation creates opportunity for organizations to fundamentally reassess and realign their workflows and staffing to enable technology success — and protect their investment.

The Solution that Introduces New Problems

Over the last decade, many nonprofits have shifted away from fundraising-specific platforms like Blackbaud toward corporate-scale CRM and marketing technologies like Salesforce and HubSpot. This trend has cut our industry both ways, positioning nonprofits to leverage best-in-class engagement platforms to amplify fundraising efforts — particularly in digital and mass market channels — while introducing new data model challenges and tech product management questions many organizations aren’t prepared to address until after they’re live on a new CRM.

Unlike their nonprofit-specific counterparts, which often offer supporting services like user training, data management, or custom reporting, corporate-scale CRMs like Salesforce rarely come with a “service bureau .” Organizations moving to these platforms may have more sophisticated business requirements, and therefore higher expectations of what the tech will enable.

The gap between what fundraising teams expect from a new CRM and what that CRM offers opens quickly. Mismanaged expectations immediately following a CRM go-live can crater users’ trust in a system or its data so dramatically, it can take years to recover. It’s between this rock-and-a-hard-place that CARE found itself in 2023, leading them to approach Skeleton Key to help explore potential new organizational models to support its Salesforce NPSP fundraising CRM.

CARE’s Challenge & Opportunity

In 2023, CARE’s CRM Team (housed in its Digital/IT department) and fundraising department (Resource Development, or RD) were fatigued from multiple years of complex CRM migrations. They brought on nonprofit consultancy Cake Byte to assess CARE’s use of Salesforce, subsequently engaging me to lay out organizational design options. Following those preliminary designs, CARE engaged me to lead a full CRM Organizational Design Assessment through fall and winter 2023-2024, where I interviewed over 50 CARE staff members to understand goals and pain points related to CRM.

Working with CARE’s Chief Information Officer and AVP of Operations, Planning & Analysis in RD, we identified three critical issues:

1. Trust and communication were breaking down, with business requirements getting lost in translation between RD and Digital, and competing priorities becoming bones of contention.
2. Users felt unsupported while the CRM Team felt overwhelmed. RD support ticket backlogs had ballooned, but the CRM Team’s overly broad remit meant user support couldn’t take higher priority.
3. Data quality eroded trust while driving up workload, with no holistic ownership leading to duplicates and errors that reinforced mistrust in Salesforce data and increasing support ticket volume.

Our design preserved CARE’s Digital CRM Team structure while building crucial capacity within RD. We created role specialization opportunities for existing CRM technical staff and recommended additional capacity for marketing technology and data infrastructure. We also established a new Development Data & Systems (DDS) team in RD to serve as business-side partner to the Digital CRM Team.

This structure allowed shared, “programmatic" ownership of Salesforce NPSP, with technical teams focusing on administration while business-side teams led user support, training, and change management; prioritized and translated fundraising requirements; and provided dedicated data quality support. Commensurate with organizational investments across RD, we also roadmapped a phased, multi-year implementation of additional DDS roles to beef up the team’s business analysis, training, and analytics capacity over time. Crucially, we designed growth paths for existing staff rather than relying on net-new headcount, seeking to align staff interests and talents with CARE’s structural needs while retaining institutional knowledge.

Success also required addressing old cultural patterns alongside structural changes, with new leadership bringing industry expertise and best practices for co-managing technology programs. A dedicated user support role in DDS dramatically improved user experience, and a dedicated data quality role allowed fundraisers to spend more time on donor relationships than wrangling data issues. The DDS and CRM teams now meet weekly to discuss backlogs, roadblocks, and risks for quicker mitigation and proactive planning, with monthly sessions to maintain alignment between Salesforce development and RD’s evolving fundraising strategies.

Invest in Relationships, Not Just CRM

CARE’s CRM success depended on careful rethinking and reconfiguration of its people and processes, alongside its technology transformation. Technology alone cannot eliminate organizational blockers — sometimes, like in any relationship, we simply have to figure out better ways to cooperate with one another.

CARE’s experience can serve as a blueprint for integrated, cross-team technology management for organizations of any size. Even if CRM ownership is housed in the same team as its core users, bridging “translation and enablement" roles are essential to successful adoption and long-term growth of systems and workflows. But here’s the catch: systems typically reflect the level of harmony or discord of the organization around them, and systems can only help integrate teams when interpersonal obstacles to integration — workflows, structures, or cultures — are also identified and resolved as part of tech transformation. Organizations enjoying the least friction and most fundraising success with their CRM invest as much in staff abilities to manage change, build trust, and sustain dynamic partnerships as they do in the software itself.

Justin Birdsong is the Founder & Principal of Skeleton Key Strategies, unlocking agile nonprofits through technology, operations, and strategy consulting. He lives in Greenfield, MA with his husband and two cats. He’d love to hear from you at greetings@skeletonkeystrategies.com.

Digital Exclusive

The Rise of Sustainable Giving: What Fundraisers Can Learn from the Subscription Economy

By Dave Raley

Each year, fewer individuals in North America give to charity.

It’s a troubling trend. But in the midst of this generosity crisis, a bright spot is emerging-recurring giving.

And not just any recurring giving. Sustainable, donor-centric, relationship-driven giving-shaped by lessons from the rise of the subscription economy.

Over the last two decades, subscription-based businesses have revolutionized the way people interact with products and services. In doing so, they’ve changed consumer behavior and expectations. For fundraisers, this shift presents both a challenge and a remarkable opportunity.

The same dynamics driving the success of companies like Netflix, Spotify, and Amazon can be harnessed to build resilient, growing recurring giving programs.

In The Rise of Sustainable Giving, I identify six key shifts driven by the subscription economy. Here are the first three-and how you can apply them to create more meaningful and lasting donor relationships.

1. From Transactions to Engaging Experiences

The best subscriptions do more than fulfill a need-they spark joy, curiosity, and delight.

Think of Spotify. For $16.37/month, I don’t just “rent music .” I get a deeply personalized, engaging experience. Spotify knows what I like. It surprises me with new artists and helps me rediscover old favorites. It’s more than a service-it’s an experience I look forward to every day.

Now, imagine your sustainer program. Is it simply a recurring payment? Or is it a meaningful, emotionally resonant experience?

My wife and I became monthly donors to International Justice Mission nearly a decade ago-because of a powerful, moving experience at a live event. That one moment has translated into eight years of consistent giving and over $2,600 in support.

Takeaway: The most successful recurring programs begin with an experience that moves people. Look for ways to delight and engage supporters-at the beginning, and all along the journey.

2. From Ownership to Access

In the past, value was about ownership. Today, it’s about access.

Why own thousands of songs when Spotify gives you access to millions anytime, anywhere?

For nonprofits, this principle translates into creating value through access-access to meaningful stories, insider updates, behind-the-scenes insights, or even community events.

Access doesn’t have to be extravagant. It just needs to be real and relevant. Exclusive webinars, early invitations to events, personal thank-you messages, or a quarterly behind-the-scenes report can go a long way in making donors feel included.

Takeaway: Ask yourself, what can you give sustainers access to that makes them feel like insiders-more connected to the cause they care about?

3. From Anonymous Buyers to Known Relationships

Before subscriptions, many businesses barely knew their customers. But with recurring relationships, data, and direct communication, they’re able to tailor experiences in increasingly personal ways.

Netflix doesn’t just stream content. It curates it-based on what it knows you’ll love.

In the nonprofit world, we’ve always had some form of direct donor relationship. But now, expectations are higher. Donors want to be known. They want a relationship that reflects their values, interests, and engagement history.

Do you know when your recurring donors give? What inspires them to give more? Have they attended an event? Volunteered? Do they always respond to certain types of stories?

Takeaway: Sustainable giving starts with sustainable relationships. Use the data you already have to personalize communications and deepen the sense of connection.

A New Era for Giving-If We Choose to Embrace It

Today, sustainable recurring giving is more accessible to more nonprofits than at any other time in history.

But access doesn’t guarantee action.

It takes thoughtful design, compelling experiences, and a willingness to adopt new models rooted in relationship and value-not just in transactions.

If you want to build something resilient-something generous, predictable, and donor-centric-there’s no better time to start.

I’ve outlined all six shifts in Chapter 8 of my book, The Rise of Sustainable Giving. You can download that chapter for free or order the full book at www.SustainableGiving.org.

Let’s build something that lasts.

Dave Raley is an author and advisor, speaker and founder of Imago Consulting, an advisory firm that helps organizations grow sustainable giving. As a speaker and advisor, Dave has inspired thousands of nonprofit leaders to grow both personally and organizationally. He’s the author of The Rise of Sustainable Giving. Dave also writes a weekly innovation and leadership column called The Wave Report, and he’s the host of both the Sustainable Giving Podcast and the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands.