CASE STUDY

Prospect Sierra: AI-Powered Advancement

Simon Tumansky
April 29, 2025
4
min read

School Profile

Prospect Sierra is a progressive TK-8 school operating across two campuses in the SF Bay Area. The school's mission is to inspire and equip students to create a more inclusive and just world through deep and meaningful intellectual engagement, self knowledge, and care for others.

Challenge

Prior to implementing ChalkBooks, Prospect Sierra's advancement team faced significant inefficiencies in their prospect research workflow. The school relied on a database system that was going unsupported and used a traditional wealth screening service that required extensive manual preparation. The process was time-consuming and cumbersome, involving hours of updating spreadsheets with constituent information and multi-day waits for results to process and be shared with the school.

"For the wealth screening it took a few hours... I had to put together a list of all our incoming families, fill in a spreadsheet with names, spouses' names, addresses and different things like that, upload it to the system, and wait for the results. Then I would run a summary and identify prospects we wanted to meet with." - Annual Giving and Alumni Relations Manager

After receiving the screening results, the team still needed additional time to identify and research prospects they wanted to meet with, creating yet another list and set of narratives for each potential donor.

Solution

Prospect Sierra implemented ChalkBooks' comprehensive advancement and prospect intelligence solution, including the Generative AI CRM and the AI Prospect Researcher tool. The school particularly values the CRM designed specifically for independent schools, which allows them to link family members in a way that reflects school relationships. ChalkBooks’ AI Prospect Researcher eliminates the manual data preparation that previously consumed so much of their time.

AI Prospect Researcher Implementation

The school started  incorporating the AI Prospect Researcher into their advancement operations this year, often using it for pre-meeting research on families. The tool allows them to instantly access constituent information with a simple name search, eliminating the multi-step process previously required for wealth screening. Using AI Prospect Researcher, members of the advancement team receive comprehensive information in minutes that helps prepare for conversations or brief others who will be meeting with the prospect.

"The ease of use and the fact that it saves so much time is mindblowing."

Results

Prospect Sierra has already experienced significant benefits from using the AI Prospect Researcher. The dramatic time savings in prospect research allows the team to be better prepared for constituent meetings. They've also achieved more efficient record keeping and donor management, enhanced monthly reporting capabilities for business office reconciliation, and streamlined pledge tracking and follow-up.

"ChalkBooks stands out because of the people who are behind it and I think that really makes a difference. It makes us feel comfortable as users and we know if something is wrong they will respond and help and give a solution."

Future Plans

The advancement team plans to expand their use of the AI Prospect Researcher in the coming school year. As they wrap up the current academic year, they intend to develop more comprehensive research strategies, increase the frequency of using AI Prospect Researcher, and explore additional AI capabilities as they develop.

Why ChalkBooks?

"We were excited about the fact they were created specifically for schools. They have knowledge of and understanding of schools in a way that a larger or more generic system doesn't have because their databases are for fundraising but fundraising in education, especially at the elementary and middle level, is different."

Prospect Sierra selected ChalkBooks over other options after careful consideration. They were drawn to ChalkBooks because it was created specifically for schools, with a demonstrated understanding of education fundraising needs. The school appreciated the responsive and personalized customer service they received throughout the selection process, as well as ChalkBooks' agile development approach to accommodate customer requests. The AI integration pointed to continued innovation that excited the advancement team.

Conclusion

By implementing the Generative AI CRM and AI Prospect Researcher, Prospect Sierra has positioned its advancement program for greater efficiency and effectiveness. The dramatic time savings and ease of use provided by AI Prospect Researcher has already impressed the team, who have plans to leverage it more strategically in the future.

" [ChalkBooks] is great…and we are very happy with the partnership."
Simon Tumansky
CEO & Founder
LinkedIn logo
April 29, 2025
4
min read