Transforming Major Gift Fundraising with a Multichannel Donor Journey

Understanding major gifts and donor journeys 

What constitutes a major gift?

A major gift is a significant philanthropic contribution that is crucial in advancing a nonprofit’s mission. While the value of a major gift varies by organization, the major gift threshold can be determined based on factors such as:

• Annual budget and operating costs – A major gift should be relative to the nonprofit’s financial scale.
• Donor history and gift patterns – What qualifies as a major gift for one organization may be a mid-level or standard donation for another.
• Fundraising goals and campaign needs – Some organizations define major gifts differently depending on specific campaigns or funding priorities.
• Community and sector norms – Nonprofits in different fields (e.g., arts, education, and healthcare) may have different expectations for major gift levels.

Examples of how major gifts vary by organization

• A grassroots nonprofit with a $500,000 annual budget may define a major gift as $1,000 or more, as such a contribution significantly impacts their operations.
• A mid-sized nonprofit with a $5 million annual budget might classify major gifts as $10,000 or more, based on typical donor capacity, giving patterns, and campaign goals.
• A large institution (such as a university or hospital) with a $100 million+ budget may consider $100,000, $500,000, or even $1 million as the threshold for a major gift.

While major gifts can come from individual donors, foundations, grantor organizations, or corporate partners, this guide primarily focuses on individual major donors—those whose giving capacity and engagement history position them as key philanthropic partners. By leveraging donor data and engagement insights, fundraisers can create personalized strategies that align with donor capacity and philanthropic priorities.

Defining major donor journeys

Donor journeys refer to the experience a donor has with an organization, from initial awareness to ongoing engagement. Understanding this journey allows nonprofits to tailor their strategies to meet donors where they are, fostering deeper connections and sustained support. While any prospect or donor can follow their own journey, here are some examples of major donor journeys based on those who have a higher capacity to give.

Examples of major donor journeys

Major donors don’t follow a one-size-fits-all path. Their engagement varies based on their giving history, interests, and relationship with your nonprofit. Below are three common major donor journeys that organizations should consider when developing engagement strategies.

New major donor journey

A prospect with the capacity to make a major gift learns about your organization—perhaps through an event, peer introduction, or mission-driven storytelling. Their journey involves personalized engagement, relationship-building, and a strategic ask that aligns with their philanthropic values.

Did you know? On average, nonprofits raising less than $10 million per year are cultivating at least 24 donors for a first-time major gift.

Major donor retention and upgrade journey

A committed donor has supported your organization with a major gift for years, but has yet to expand their impact. Encouraging continued engagement through meaningful recognition, shared impact stories, and aligned giving opportunities can lead to increased support or new involvement.

Lapsed major donor reactivation journey

A previously engaged major donor has not given in several years. Whether due to shifting interests, financial changes, or a lack of recent engagement, reactivating their involvement requires thoughtful re-engagement, mission updates, and opportunities that inspire renewed support.

Recognizing these donor journeys is just the beginning. To cultivate and sustain major donor relationships, nonprofits must implement a multichannel engagement strategy that nurtures donors at every stage. Next, we’ll explore common challenges fundraisers face in major gift development, followed by a deep dive into how nonprofits can apply a data-driven major donor journey approach (without fear) to enhance engagement, retention, and impact.

Common fears in major gift fundraising: Turn your roadblocks into roadmaps

Despite the critical role of major gifts in nonprofit success, many fundraisers face hesitation and uncertainty during the process. Whether it’s identifying the right donors, making the ask, or handling rejection, these fears can create roadblocks to securing transformational gifts. The good news is that these challenges can be overcome with strategic approaches and a donor-centered mindset.

Here are some common fears, challenges, and solutions that fundraisers can face when working to secure major gifts from new and existing donors. Later, we will connect these concepts to major gift donor journeys.

Fear #1: Measuring success in major gift fundraising

Challenge: Quantifying success in major gift fundraising can be ambiguous, leading to uncertainty about the effectiveness of strategies.

Solution: Tracking and analyzing key performance indicators (KPIs) can help fundraisers assess progress, refine their approach, and ensure long-term major gift success. Consider the following strategies:

• Donor retention – Track the rate at which major donors continue their support over time.
• Gift upgrades – Monitor increase in donation amounts from existing major donors.
• Engagement metrics – Assess the frequency and quality of interactions with current and prospective major donors.
• Touchpoint analysis – Evaluate the effectiveness of various communication channels in reaching and resonating with donors.

Fear #2: Identifying potential major donors 

Challenge: Identifying individuals with both the capacity and willingness to make significant contributions can be daunting.

Solution: Leveraging data-driven insights and donor engagement tracking can help fundraisers identify and prioritize prospective major donors more effectively. Key strategies include:

• Data analysis – Utilize donor management systems to analyze giving histories and identify patterns.
• Wealth screening – Employ tools that assess a prospect’s financial capacity to give.
• Engagement tracking – Monitor interactions to gauge a prospect’s interest and readiness to contribute.

With DonorPerfect’s DonorSearch integration, you can perform prospect research and wealth screenings to uncover major donors in your system and network.

Pro tip: Run annual reports to catch automatic or non-recurring gifts from donors to see if they reach major donor status at your nonprofit. Recurring donors could be hidden major donors!

Fear #3: Determining the appropriate solicitation amount for a major gift

Challenge: Asking for too much or too little could jeopardize the donor relationship and the potential gift.

Solution: Conducting thorough research and aligning the ask with a donor’s capacity and interests can increase the likelihood of a successful solicitation. Fundraisers should consider:

• Research – Investigate the donor’s giving history and capacity.
• Capacity assessment – Align the ask with the donor’s financial ability and philanthropic interests.
• Alignment with donor interests – Ensure the proposed project or initiative resonates with the donor’s passions.
• Range – If deciding on a single number after your research is challenging, consider presenting a range based on your donor’s giving history and capacity. For example, “Would you consider a gift between $50,000 and $75,000?” This provides flexibility while encouraging the donor to consider the higher amount.

Pro tip: Leverage data-driven insights like capacity range based on wealth (estimated 5-year giving capacity range based upon a combination of real estate, stock information, business revenues, political giving, and pension info) to refine your solicitation strategy. Analyzing a donor’s past giving history, wealth screening indicators, and engagement trends can help determine an appropriate ask amount. Use engagement models and predictive modeling to align your request with the donor’s giving potential while ensuring it feels both aspirational and achievable.

Fear #4: Handling rejection with major donors

Challenge: The emotional toll of rejection can deter fundraisers from making initial contact or making future asks if communication or visits do not have positive outcomes.

Solution: Reframing rejection as an opportunity for learning and relationship-building can help fundraisers maintain donor engagement and refine future approaches. Consider these steps:

• Seeking feedback – Understand the reasons behind the decision to refine future approaches; ask clarifying questions about communication preferences. 
• Maintaining engagement – Based on their preferences, continue to involve the donor in your organization’s activities, and share impactful mission updates. 
• Adjusting strategies – Be flexible and willing to modify the approach based on donor feedback and changing circumstances.

Pro tip: Often, a donor is not able to give at the moment (not the right time) or is thinking about their budget (the right amount) so be patient and understanding while trying to secure a meeting or major gift funding.

Fear #5: Avoiding common pitfalls in major gift fundraising

Challenge: Even experienced fundraisers can fall into common traps that can jeopardize donor relationships and major gift opportunities. From misjudging timing to relying too heavily on a single approach, these missteps can lead to disengagement, lost gifts, or donor fatigue.

Solution: Being mindful of these pitfalls and adopting best practices can help fundraisers navigate major gift cultivation more effectively. Here’s what to watch out for:

• Asking without permission – When working with major donors, don’t assume you know their preferences or decision-making timeline. Instead, ask permission at key moments to ensure alignment and that trust is being built. Instead of sending an unsolicited proposal, say:
  • “Would it be helpful if I put together a proposal outlining potential impact areas?”
  • “Would you be open to discussing how your philanthropy could help us achieve this vision?”
• Over-rehearsing the ask – While preparation is key, sounding overly scripted can make conversations feel transactional rather than relational. Aim for confidence, not perfection, and allow room for natural dialogue.
• Using impersonal outreach – Generic mass emails or templated solicitations can make donors feel like just another name on a list. Instead, personalize communication based on past interactions, interests, and giving history.
• Reaching out to lapsed donors without context – Jumping straight into a solicitation without acknowledging a donor’s absence can feel abrupt. Instead, rebuild the relationship first by sharing impact updates and expressing genuine appreciation for their past support.
• Soliciting too soon – Asking for a major gift before the donor is ready can backfire. Focus on relationship-building first, ensuring the donor is engaged and aligned with the mission before soliciting a donor.
• Relying on a single communication channel – Donors engage in different ways, so only using email or phone calls can limit connection. Implement a multichannel strategy that includes direct mail, social media, in-person events, and personalized digital outreach to reinforce engagement.

By addressing these common fundraising fears, taking calculated risks, and embracing a thoughtful, donor-centered approach, fundraisers can create personalized donor journey roadmaps to cultivate stronger relationships and improve major gift outcomes.

With DonorPerfect, you can create simple, sophisticated reports to analyze your fundraising efforts and summarize donor information, giving history, and engagement notes.

Implementing a multichannel major donor journey strategy 

While any donor can engage with your nonprofit, major donors have unique engagement paths that require tailored strategies. Whether they are new major donors, upgrading their gifts, or reactivating after a lapse, understanding their journey ensures fundraisers can personalize outreach, deepen relationships, and secure long-term commitment.

By leveraging CRM tools like DonorPerfect, nonprofits can automate key touchpoints along the donor journey—personalized thank-yous, engagement tracking, and tailored appeals based on giving behavior. Learn more in The Donor Journey — a free guide from Cherian Koshy, CFRE, and the experts at DonorPerfect.

Here’s how a multichannel donor journey approach applies to major donors at different engagement stages:

Major donor journey scenarios 

1. New major donor journey: Engaging a first-time major gift prospect without fear

Scenario: A prospective donor attends a university’s scholarship lunch and expresses interest in establishing a named, endowed scholarship to support undergraduate students. Aside from being a one-time event attendee, there are no other details about this prospect in your nonprofit CRM.

Multichannel engagement strategy

Immediate follow-up:

• A personalized thank-you email from the director of development or development team leadership, thanking them for their interest
• A handwritten note from a current scholarship recipient sharing how donor support makes a difference

Personalized education and engagement:

• A curated impact report on existing scholarships, showcasing student success stories
• An exclusive invitation to meet faculty members leading the scholarship program

Seamless transition to solicitation:

• A one-on-one meeting to discuss scholarship funding options (endowed, multi-year, or annual gifts)
• Gift range presentation to align with their financial capacity and philanthropic goals

Key outcome: The donor makes a $50,000 initial commitment to name an annual scholarship fund and is welcomed into an exclusive donor recognition society, with a plan to meet student scholarship recipients.

2. Major donor upgrade journey: Moving a loyal major donor to a higher giving level while navigating some hesitation around endowments

Scenario: A donor has contributed $25,000 annually for five years to a non-endowed fund, but has not increased their giving. The donor recently attended a capital campaign event and expressed interest in expanding their support, but has hesitations about giving to an endowed fund versus an annual fund.

Multichannel engagement strategy

Reinforce their impact:

• A custom impact report showing the direct effects of their previous gifts
• A personalized thank-you video from the executive director highlighting their role in the organization’s success

Introduce an upgrade opportunity:

• A special briefing call to discuss new initiatives that align with their interests
• A peer-driven approach, such as a board member who has also increased their giving reaches out to share why they upgraded to support an endowed fund, a way that will support the program in perpetuity

Create a transformational giving proposal:

• A proposal offering naming opportunities (e.g., a scholarship fund or an educational program)
• Strategic follow-ups across different channels via email, in-person meetings, and direct mail, reinforcing the donor’s potential impact

Key outcome: The donor increases their annual commitment to $50,000 to support immediate needs, and pledges an additional $250,000 to the capital campaign’s endowed fund to establish a new, named scholarship fund.

3. Lapsed major donor reactivation journey: Re-engaging a previously engaged major donor

Scenario: A donor who previously gave $100,000 annually has not made a gift in three years. They have stopped attending events and haven’t responded to recent solicitations.

Multichannel engagement strategy

Authentic acknowledgment and warm reconnection:

• A personalized letter from a board member, acknowledging their past generosity and inquiring about their current interests to better understand why they stopped giving or to learn about new passions
• A no-ask outreach call to check in, share updates, and express gratitude for their past support

Exclusive re-engagement opportunities:

• A private tour or VIP event invitation showcasing a new initiative
• A custom impact update showing how their past gifts still contribute to the nonprofit’s mission

Thoughtful gift reintroduction:

• Instead of immediately soliciting a large gift, offer a small, targeted giving opportunity that aligns with their past philanthropy.
• If they respond positively, transition to a larger discussion about long-term giving.

Key outcome: After some meaningful discussion, the donor re-engages with a $25,000 renewal gift and agrees to explore a larger commitment in the next fiscal year.

Key takeaways

• A major donor’s journey is non-linear—they engage at different stages, across different channels, and at their own pace.
• Leveraging a multichannel approach ensures that fundraisers are meeting donors where they are, rather than following a rigid step-by-step process.
• Personalized engagement and technology-driven insights create seamless donor experiences that maximize long-term giving potential.
• Major donors don’t just give once—they can become your strongest advocates when cultivated and stewarded effectively.

To learn more about donor journeys, check out our latest blog: Donor Journeys: What They are & How to Personalize Them. 

Most donors expect ongoing, personalized interactions across multiple channels. Adopting a donor journeys fundraising strategy allows nonprofits to build deeper relationships, increase donor retention, and secure transformational gifts that drive mission impact. A well-executed multichannel donor journey strategy ensures that every major donor feels heard, valued, and inspired to continue supporting your organization for years to come.

DonorPerfect’s powerful donor management tools empower nonprofits to track engagement, personalize outreach, and steward major donors with confidence. Ready to transform your fundraising strategy? Download your free Donor Journey guide today and start building stronger donor relationships.