.png)
Robert Montgomery is a highly accomplished nonprofit executive with over 30 years of experience in organizational leadership, fundraising, and community development. He has written and published a book about his experiences as a nonprofit executive that is now available on Amazon.
Robert has held pivotal leadership roles at organizations such as the United Way and Boys & Boys Clubs, where he managed a diverse portfolio of programs and generated significant revenue through innovative fundraising initiatives. He orchestrated a remarkable financial turnaround, eliminating $200,000 in debt and securing major gifts to ensure sustainability. He spearheaded a 57% increase in corporate giving, and raised millions for local charities through strategic campaigns and public speaking engagements.
Robert’s fundraising journey began as a minister at the Chicago Church of Christ, where he honed his skills in relationship management and grassroots mobilization. His ability to inspire and engage stakeholders has been a hallmark of his career, enabling him to raise millions for causes ranging from affordable housing to refugee assistance.
A visionary leader, Robert holds a Bachelor of Arts in Urban Planning from the University of Illinois at Urbana-Champaign and a Master of Urban Planning and Policy from the University of Illinois at Chicago. His mission is to create blueprints for success that empower underprivileged communities through self-sufficiency, collaboration, and mutual inspiration. With a proven track record of transforming organizations and amplifying their impact, Robert continues to drive change by uniting strategic planning with unwavering dedication to service.
Client Testimony
Working with Robert Montgomery has been such a valuable experience for me and for Don’t Stop Belizein. He has been instrumental in helping us think more strategically about our fundraising approach and donor outreach.
Robert brings a depth of expertise and clarity that has helped us refine our priorities, strengthen our message, and plan ahead with confidence. His thoughtful guidance has given me concrete steps and a bigger picture vision for how to engage donors more effectively and sustain our mission over time.
I’m grateful for his support and highly recommend Robert and Rosemoor LLC to anyone looking to strengthen their fundraising strategy and donor engagement.

Grant Writing Services
Rosemoor LLC empowers nonprofits to secure grant funding by managing the entire grant lifecycle from start to finish. We begin by conducting in-depth research to identify the most aligned funding opportunities based on your mission, programs, and capacity. We then craft compelling, tailored proposals that highlight your organization’s impact while ensuring strict compliance with funder guidelines. Beyond securing awards, we handle post-award grant management, including reporting and stewardship, so you can focus on delivering your mission. With Rosemoor LLC as your partner, you gain a strategic, hands-off approach to grant funding that maximizes success and sustainability.
A
Grant Research
Rosemoor will help your organization identify and secure grants by carefully researching funders whose missions and guidelines align with your goals, ensuring each opportunity is a strong match for your programs, capacity, and funding needs.
B
Grant Applications
Rosemoor will expertly guide you through the entire grant writing process. Crafting compelling narratives, developing strong proposals, and completing applications with precision to maximize your chances of securing funding while saving you time and effort.
C
Grant Reporting
Rosemoor will ensure your grant compliance and foster strong funder relationships by managing timely, high-impact reports, meeting all deadlines, and strategically stewarding grantors to maximize ongoing and future funding opportunities.
Major Gift Solicitation: 4 Step Process
The major gift solicitation process for a nonprofit involves identifying, cultivating, and soliciting high-capacity donors who can make significant contributions to advance the organization’s mission. It begins with researching and prioritizing prospective donors based on their giving history, capacity, and alignment with the nonprofit’s goals. Cultivation is key for building relationships through personalized communication, engagement opportunities, and demonstrating impact. Once a strong connection is established, a tailored ask is made, often in person or through a meaningful proposal that aligns the donor’s interests with a specific funding need. Stewardship follows, ensuring donors feel valued through recognition, updates, and ongoing engagement to foster long-term support. The process relies on thoughtful strategy, relationship-building, and clear communication to secure transformative gifts.
Rosemoor will manage your major gift solicitation process and help you build a pipeline of prospective donors, ensuring efficiency and accountability. We will oversee prospecting, track donor research, engage touchpoints, and administer solicitation readiness in a structured online data system. We prioritize prospects, schedule cultivation steps, and coordinate a steady flow of solicitation meetings for your executive director (ED), and board members, based on monthly goals, such as a desired number of asks per month. By aligning the ED’s availability with the pipeline’s most promising opportunities, Rosemoor ensures consistent donor outreach while avoiding gaps or overload. Regular pipeline reviews help adjust strategies, track progress toward revenue targets, and maintain momentum in securing major gifts. This disciplined approach maximizes the ED’s time and increases the likelihood of successful solicitations.
1
Goals & Stats
Determine number of prospective donors
2
Donor Mining
Accumulate a list of prospective donors
3
Planning
Research and develop customized proposals
4
Execution
Conduct solicitation visits

