News, commentary & industry best practice for advancement professionals


The Weekend Briefing is distributed every Sunday evening by email to development officers around the country.

Written by Rob Cummings, The Weekend Briefing brings practical information and best practice in fundraising to development professionals who work without the resources and support enjoyed by larger institutions.

Yet the Briefing finds an audience among fundraisers at every level of experience and among organizations of every size.
The art and science of this noble profession unite us all.

You have indeed mastered the art of fundraising and the ability to share, delight, and inspire the rest of us.”

Every Sunday I look forward to The Weekend Briefing. Thank you for sharing your wisdom and providing an opportunity for fellow advancement professionals to learn week after week.”

“Thanks for your commitment to sharing your thoughts and reflections, and ideas, with all of us. No matter where we are in this work, it has value for us.

“I believe the Briefing serves to build our community by supporting fundraising professionals at all levels and from all kinds of institutions, effectively reminding even experienced professionals of key tenets, lessons learned and shared experiences. When I receive the Briefing, I think of colleagues around the country who are probably also smiling at your examples and stories and nodding their heads in recognition of the lesson shared, as I do. You reinforce that sense of community among us all.”




Rob Cummings’ career spans 39 years as a development leader for many of the Chicago area’s oldest and most respected institutions. Through his deep understanding of the field and his capacity to nurture the growth of development professionals, Rob has established a distinguished record of success in major gift solicitation and building strong fund raising programs.

Rob Cummings

Over much of the last decade, Rob transformed the development program of the Chicago Lighthouse for People Who Are Blind or Visually Impaired into one of the most respected of its kind in America, successfully spearheading a $17 million Centennial campaign and raising $25 million overall.

Beginning his career at St. Ignatius College Prep, Rob crafted the strategy for the first Campaign for St. Ignatius, funding the rebirth of that famed Chicago institution. His leadership at both Loyola University Medical Center and Saint Xavier University saw the first seven-figure gifts from living donors to each institution and a notable advancement of their fund raising programs. Rob served as national Vice President for Advancement for the Cristo Rey Network of schools and as chief development officer for the five Franciscan Alliance hospitals in Northern Indiana. He is now chief development officer for the Midwest Province of the De La Salle Christian Brothers.

Rob co-founded Chicago’s Archdiocesan Development Council and has been a regular speaker for virtually every major fund raising organization, including CASE and AFP. He is the recipient of the Distinguished Service Award from Big Brothers Big Sisters of Metropolitan Chicago, two Golden Trumpet Awards from the Publicity Club of Chicago, and the St. Ignatius Alumni Medal.

At present, Rob is completing work on his first book, “North Star: Stories of Best Practice in Fund Raising”. He is the author of “The Weekend Briefing”, a digest of news, commentary, and industry best practice distributed every Sunday night to 1,000 advancement professionals across the country. An alumnus of John Carroll University, Rob holds a bachelor’s degree in English.

He and his wife, Linn, have three grown children and reside in Lemont, Illinois.

Rob can be contacted at



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