A distinguished panel of retired nonprofit executives and fundraising leaders from the Pittsburgh region for a candid conversation on the evolution of philanthropy and the nonprofit sector. Drawing from decades of experience, panelists will reflect on how donor engagement, fundraising strategies, volunteerism, and community partnerships have transformed over the years. Attendees will gain valuable insight into the challenges and opportunities that have shaped the field, while exploring how emerging professionals can adapt to the future of philanthropy with innovation, authenticity, and purpose.
Breakout Sessions
(Click on the links to read a full desciption of the session)
20 Hacks for Small Shop Fundraisers
Fundraising in a small shop comes with its challenges. Limited capacity, less than ideal infrastructure, and not enough time in the day can leave the most dedicated professional spinning in circles. Whether you’re a seasoned professional working in a small shop for the first time or a fundraising newbie who is just getting their feet wet--learning new ways to make your work more efficient and streamlined (without just relying on AI!) is always valuable. Join Hannah Sherer and Andrea Glickman of Procopia as they share 20 hacks for fundraising success. This session will allow space for regular contributions from the group to make it a lively discussion and sharing opportunity.
Goals:
-Provide 20 bite-sized practical hacks for various aspects of fundraising, specially geared towards small nonprofits (less than 1M operating budget and/or a one or two person development team)
-Engage participants by structuring opportunities for reflection and sharing throughout the presentation
Topics covered:
-Grantseeking and grantwriting
-Corporate Giving and Sponsorships
-Prospect Research
-Major Gifts
-Small Shop Hurdles
-Annual Giving
-Digital Fundraising
-AI and other technologies to enhance fundraising
Materials provided:
-Copy of the slide deck
-Reflection questions
A Gift Officer's Guide to Engaging Your Board in Fundraising
Board members often want to be helpful. But without clear structure, tools, and the right guidance, that willingness doesn’t always translate into meaningful fundraising action. This session focuses on how intentional organizational design, paired with straightforward tools and relationship-based conversations, can improve board engagement in philanthropy.
This session will offer a fundraiser’s perspective on a Board Liaison model—where gift officers each support a small group of trustees, creating shared ownership that increases clarity, consistency, and accountability. Attendees will learn how this defined liaison role helps to normalize expectations for board members, supporting their role both as donors and as fundraisers.
We will explore how simple, low barrier tools, such as an annual check-in meeting and prospecting worksheet, can capture how board members prefer to help, who they are connected to, and what excites them most about the mission. These tools make follow-through easier for fundraisers and trustees and help move conversations from vague interest to specific, achievable action aligned with each board member’s strengths. Rather than asking every trustee to “ask,” this approach creates multiple, meaningful pathways for engagement that support stronger relationships and better fundraising outcomes.
Participants will leave with a framework for structuring board relationships, practical tools they can adapt immediately, and conversation strategies that help trustees show up as confident, effective partners in philanthropy.
A Heavenly Match: The Marriage of Planned Giving & Direct Marketing
Planned gifts don’t just happen; you have to ASK for them. You have all heard of the Great Wealth Transfer – with upwards of $120 billion passing between generations in the next few decades. It’s happening now, and if your organization is not marketing planned gifts, you are already late to the party. In this session, you’ll hear from seasoned direct marketing and gift planning leaders about how to use direct response to generate planned giving leads and increase your organization’s share of the Great Wealth transfer. We’ll share actual examples of campaigns that have produced strong results and discuss how your gift planning and direct marketing teams can work together.
AI Without the Guilt: Building Trust and Guardrails for Smarter Fundraising
AI is already in your inbox. The question isn't whether to use it—it's how to use it well. This session cuts through the hype and addresses what fundraisers actually worry about: Am I compromising donor relationships or privacy? Will this damage trust if they find out? Where are the real ethical lines?
We'll walk through practical principles for integrating AI into fundraising without sacrificing authenticity. You'll learn what AI can legitimately strengthen—prospect research, brain storming, draft language, capacity building, time management—versus where it creates real risk. We'll cover digital fundraising guidelines, transparency with leadership, and how to use AI as a thinking partner, not a replacement for your judgment.
Leave with a framework you can actually use and the confidence to make these decisions on your own.
Beyond the Grant: Building Strategic Partnerships that Fund Mission and Community Impact
Nonprofits today are being challenged to do more than secure funding. They are being asked to build meaningful relationships, create community impact, and develop partnerships that align with both mission and long-term sustainability. This session will explore how organizations can move beyond transactional sponsorships and cultivate strategic partnerships that increase visibility, strengthen credibility, and open doors to new opportunities for growth and support.
Drawing from real-world experiences leading Moonshot Museum and helping secure transformational partnerships and funding opportunities, including a nearly $800,000 NASA award, attendees will gain practical insights into relationship-driven fundraising, mission alignment, community engagement, and partnership development. Through storytelling, practical examples, and discussion, participants will leave with actionable ideas for building authentic collaborations, positioning programs for support, and creating partnerships that benefit both their organizations and the communities they serve.
Building a Strong Donor Pipeline
Goals: provide a plan to help develop a donor pipeline in your shop; topics include: how to use wealth screenings, retention strategies, reports that matter, effective moves management
Composure is a Skill: Using AI to Train Judgement and Reclaim the Gift Officer's Day
Composure is the quiet variable that separates the gifts we close from the ones that slip away. It is the gift officer's ability to walk into a high-stakes conversation rehearsed, present, and unburdened by the administrative weight of the trip that got them there. And it is in short supply across our profession; not because officers lack skill, but because the modern advancement workday leaves almost no room to cultivate it.
This session introduces a practitioner built AI operating system designed to restore composure to the major gift role. Drawing on 15 years in advancement, a live deployment at Carnegie Mellon University, and use at other R1 institutions, the presenter will walk through three integrated tools that function less like software and more like a training environment for human judgment: an adversarial conversation simulator (The Development Dojo) that lets officers rehearse difficult asks against synthetic donor personas before the real conversation ever happens; a voice-to-CRM synthesis tool that turns a two minute drive time debrief into a complete contact report; and a travel and visit planning compressor that reduces days of itinerary work for the year to minutes.
Attendees will see live demonstrations, hear candid lessons from a the impact on the principal gifts cycle that served as the platform's first proof of concept, and leave with a framework for thinking about composure as a trainable, measurable discipline rather than an innate trait.
Goals of the Session
Attendees will leave able to:
Define philanthropic composure as a trainable skill and identify the workflow conditions that erode it inside most advancement shops.
Map the three highest-leverage points where AI can restore composure — by compressing administrative time, sharpening conversational preparation, and reducing the cognitive load of follow-up.
Distinguish between AI tools that replace the officer's judgment and AI tools that train and protect it — and articulate why the distinction matters for both donor outcomes and team retention.
Apply a practical framework for piloting composure-focused AI tools inside their own shops, including governance considerations around donor data, synthetic personas, and digital likeness.
Topics Covered
The composure problem: what officers are actually losing when 60–70% of the workday is administrative, and why traditional training models fail to close the gap
TRAIN — The Development Dojo: an adversarial simulation engine that lets gift officers rehearse against synthetic donor personas — different relational postures, motivations, and resistance patterns — before the real meeting, with a debrief and progression system modeled on flight simulation and athletic training
KNOW — Voice-to-CRM synthesis: turning windshield time into structured contact reports, so the officer arrives at the next meeting with cognitive load already cleared
GO — Travel and visit planning compression: reducing trip prep from hours to minutes so officers spend their best energy on donors, not logistics
The governance question: why simulation on synthetic archetypes is defensible while behavioral cloning of real donors is not, and what advancement leaders need to know about ADMT, the EU AI Act, and digital likeness protections
Lessons from the field: a candid look at what worked, what failed, and what surprised the presenter during a live deployment at an R1 institution, including a 120-day principal gift cycle that became the platform's proof of concept
A composure-first pilot framework for advancement leaders considering AI adoption
Creating Momentum in a New Development Role
Starting a new development position can feel overwhelming. New fundraisers are often expected to build relationships quickly, establish credibility internally, manage competing priorities, and demonstrate measurable progress within the first few months, often without clear roadmaps or fully developed systems.
This session provides practical strategies for creating early momentum in a new fundraising role through intentional relationship-building, portfolio development, strategic activity management, and organizational alignment. Drawing from experience launching and rebuilding major gift portfolios multiple times, this presentation will focus on how development professionals can create visible progress while laying the foundation for long-term success.
Participants will explore practical frameworks for prioritization, prospect qualification, internal partnership-building, and establishing productive habits that drive sustainable fundraising outcomes.
Topics covered will include:
● Building credibility with leadership and internal stakeholders
● Developing productive outreach and follow-up systems
● Creating and prioritizing a prospect pipeline
● Balancing short-term expectations with long-term relationship development
● Managing time, focus, and competing priorities
● Identifying and leveraging early wins to create organizational confidence
● Practical lessons learned from early portfolio development work at Fairmont State University and WVU
The session will include practical frameworks, real-world examples, audience discussion, and actionable implementation strategies attendees can apply immediately.
Audience materials will include:
● A first 90-days strategy framework
● Sample outreach and follow-up ideas
Emerging Strategies: Five Case Studies in Transformational Fundraising
What does transformational fundraising actually look like in practice? In this session, nonprofit leaders will share candid case studies of strategies that exceeded expectations — and why. From an innovative commemorative campaign that closed out Pittsburgh Glass Center's capital campaign with over $100,000, to a peer-to-peer board campaign that produced 100% participation and nearly $3 million in gifts for The Woodlands; from Literacy Pittsburgh's decision to cancel their signature event last year that resulted in more funds raised in corporate sponsorship without the costs of an event, to CC Mellor Memorial Library surpassing a $2.2 million campaign goal with no professional development staff, to The Citizens Science Lab's cultivation of a nominal corporate gift into a transformational naming opportunity — these are real stories of creative thinking, strong relationships, and bold moves. Attendees will leave inspired with practical strategies they can adapt for their own organizations.
Grant Writing Crash Course: Tactics to Write Strong Grants and Manage Your Grant Pipeline
This session provides a practical, accessible introduction to grant writing for nonprofit professionals, grassroots organizers, and community advocates. Using real-world examples and interactive discussion, participants will learn how to identify funding opportunities, assess grant fit, write compelling narratives, and manage the full lifecycle of a grant—from prospecting and drafting to reporting and renewal.
Topics covered will include where to find grants, what makes an organization “grant-ready,” how to write strong and concise narratives, understanding the difference between concept notes and full grant proposals, SMARTIE goals and deliverables, budget planning, funder alignment, grant tracking systems, reporting requirements, and ethical considerations in fundraising and AI use in grant writing. The session will also explore practical systems for grant management, collaboration, and long-term sustainability.
Audience materials will include a grant calendar template, answer sheet template, grant file management examples, sample grant applications, and practical tools participants can immediately adapt for their own organizations. Time will also be reserved for audience questions, troubleshooting, and discussion of common anxieties and challenges related to fundraising and grant writing.
Benefit to participants:
-Participants will be able to assess whether an organization is “grant-ready” by identifying the core operational and financial systems needed before applying for funding.
-Participants will be able to draft stronger grant narratives by incorporating concise writing, SMARTIE goals, funder-aligned language, storytelling, and data-informed framing techniques.
-Participants will be able to implement basic grant management systems, including grant calendars, tracking tools, file organization practices, and reporting workflows.
-Participants will be able to identify ethical considerations in fundraising and discuss both the opportunities and limitations of using AI tools in grant writing and nonprofit work.
-Participants will leave with practical templates, sample materials, and actionable tools they can immediately adapt to strengthen their organization’s fundraising capacity.
Launch Your SMS Program: How to Build Your Next Core Fundraising Channel
Texting has quickly moved from an emerging tactic to a core fundraising channel—and for good reason. SMS allows nonprofits to reach supporters with immediacy, relevance, and scale, strengthening results across acquisition, engagement, and response.
In this session, Conservation International and MissionWired will share how CI launched an SMS program to complement its digital fundraising strategy and meet donors where they are. Speakers will walk through how SMS helped strengthen multi‑channel campaigns, support key giving moments, and potentially offset pressure on traditional channels like email. The discussion will explore why launching an SMS program now can future‑proof fundraising, the key considerations for getting started, and what early success looks like for organizations building SMS programs from the ground up.
Whether you’re considering SMS for the first time or looking to expand your channels, this session will offer practical insights into making texting a powerful part of your fundraising strategy.
Leading with Confidence: Career Growth & Inclusive Leadership for Nonprofit Professionals
This session is designed to help nonprofit and philanthropy professionals build the confidence, clarity, and leadership presence needed to grow in mission‑driven environments. Whether participants are early in their careers or navigating a mid‑career pivot, this session provides practical tools for advancing with purpose — without burning out.
Drawing from my experience coaching 200+ women and emerging leaders, including two Allied Health Excellence Award recipients and a Latina deputy director who successfully led her division through a complex merger, this session blends leadership development, confidence building, and equity‑centered career strategy. Participants will explore how to articulate their strengths, communicate their value, and lead authentically in diverse, high‑impact settings.
The session will cover:
Identifying your leadership identity and translating it into career advancement
Building confidence and navigating internal and external barriers
Inclusive leadership practices that strengthen team culture and donor relationships
Career pivots and transitions, including moving into consulting or non‑traditional roles
Communication strategies that elevate visibility and influence
Mindset tools for overcoming imposter syndrome and leading with clarity
Participants will receive:
A Leadership Identity Worksheet to clarify strengths and values
A Career Clarity Roadmap for planning next steps
A Confidence‑Building Toolkit with practical exercises
Reflection prompts to support ongoing growth
The session is interactive and includes small‑group discussion, guided reflection, and real‑world case examples. Attendees will leave with actionable strategies they can apply immediately to strengthen their leadership presence, navigate career transitions, and grow with confidence in the nonprofit and philanthropic sectors.
Legacy Giving Blitz: Lessons and Resources from an 18 Month Intensive Focus on Launching a Planned Giving Program
How can a small fundraising shop effectively launch a formal planned giving program? In this session, participants will learn how Allies for Health + Wellbeing implemented guidance from a national foundation to identify, cultivate, solicit, and steward legacy gifts. From policies and paperwork, to communications plans and board training, Senior Director of Development and Marketing Alex Neal will share lessons learned from a short and intensive focus on building a legacy giving program from scratch. Resources will be shared with participants including: sample Letter of Intent, Ways to Give, and Implementation Planning documents.
Legal Issue Spotting for Charitable Fundraising
The goal is to provide attendees with an introduction to common legal issues that arise in fundraising. The topics will include charitable solicitation registration, corporate sponsorship, games of chance, introduction to the unrelated business income tax, public charity vs. private foundation, joint ventures, and what a board needs to know about endowments. This will be a high level overview of the issues that come up in fundraising.
Planned Giving Within Reach
When the topic of planned giving (arranging now for a future contribution, usually upon a donor's death) comes up, even the most veteran fundraising professionals often start to squirm. It can be overwhelming to know where to start, the technicalities of giving vehicles can be confusing, and the idea of talking to people about something that involves their death can be uncomfortable. Accordingly, many small, community-based nonprofits shy away from planned giving.
Yet it doesn’t have to be this way! Planned giving is an enormous revenue opportunity for organizations of all sizes, and with some easy-to-do planning and basic strategizing, planned giving can be done simply, joyfully, and successfully.
Learning Objectives:
1. Attendees will feel empowered to engage with planned giving donors
2. Attendees will have a roadmap to follow to launch a planned giving program
3. Attendees will learn a basic approach to planned giving that works for small nonprofits
Speaking in Ages 2.0: How Small Shops Talk to Their Most Valuable Donors
Your most loyal, highest-capacity donors are likely over 65. And most of what fundraisers learned about donor communication does not apply to them. Not because older donors are difficult: because they are different. They make decisions differently, respond to urgency differently, and think about legacy in ways that standard major gift training rarely addresses.
Speaking in Ages 2.0 adds to the research of Russell James and David Solie, with new material from The Longevity Economy, Laura Carstensen, and others. Attendees leave with a practical framework for talking to their most tenured donors more effectively: why urgency backfires, how donor stories outperform gift vehicle explanations, and how to recognize when a loyal annual donor is ready for a different kind of conversation. We close with low-cost visibility strategies any small shop can sustain.
The 5 Ways Companies Say YES
What if companies are willing to say yes in more ways than you’re asking? This interactive workshop introduces a practical framework to uncover multiple pathways for corporate engagement beyond traditional sponsorships. Participants will explore how to better align with corporate priorities, identify untapped opportunities, and develop more strategic, relationship-driven approaches that can lead to stronger, more sustainable partnerships. Learn to switch your mindset from asking for support to helping companies solve problems.
Agenda:
Welcome & Reframing the Ask
Shift from transactional sponsorships to strategic engagement
The 5 Ways Companies Say Yes
A practical framework for expanding corporate partnership opportunities
Interactive Exercise: Expanding Engagement
Participants map multiple engagement opportunities for a target company
Understanding Corporate Priorities
What companies value and how nonprofits can align (possible corporate rep. here)
Hands-On Activity: Rethinking the Ask
Transform a traditional sponsorship request into a multi-dimensional partnership
The Planned Giving Donor Engagement Handbook
We will cover donor cultivation from the date the first meeting is secured, meeting preparation, meaningful follow up, discussion of planned giving options and tax implications, matching donor assets to the best planned giving options and provide tax considerations/benefits to share with your donor.
We will cover all aspects of donor cultivation, technical planned giving talking points, how to identify the best planned giving options for a donor with real life donor cultivation examples and will finish with best practices for stewardship. We will discuss how to effectively move a donor through the cultivation process to gift closure to maximize support for your organization including techniques to move a slow-moving cultivation to closure.
The Stewardship Sparkle: How we Suprise and Delight our Supporters
Great stewardship starts with a strong foundation. Using a “cake” framework, this session explores how to layer essential practices (batter), thoughtful enhancements (icing), and personalized touches (sprinkles and decorations) to create meaningful donor experiences. Learn how to balance consistency and creativity, use smart segmentation to tailor outreach, and add “surprise and delight” moments that deepen engagement without overextending resources.
Goals of the Session: Attendees will walk away with an understanding of stewardship strategies that fit their organization and ways that they can implement high impact touchpoints.
Materials Provided to Audience: Stewardship one-sheet and example references from the Food Bank
There are No Small Events! Raise More, Spend Less, and Keep Your Team Focused on What Counts
With nearly two decades of corporate fundraising event experience for a local nonprofit, there isn’t much I have seen, or tried – once or twice! From bag pipers to cash cubes – I’ve thrown everything but the kitchen sink at fundraising events to get the most bang for a buck. What I learned was that events are fun, rewarding, emotional, and inviting, but often drain the very life out of a fundraising team. In smaller nonprofits, it might feel like you’re suffocating from the endless to-dos that come with, let’s face it, year-round event planning. And, let's be honest, hiring an event planner is never going to make it into the budget.
Participants will leave the session with the confidence to say “enough!” to endless hours cultivating mediocre, one-off sponsorships, skimping on food, and begging your board members to buy a table, all while time ticks away, along with your sanity. Attendees will be given ideas on how to determine whether your “small” gathering could have raised more as an email and how to eliminate the noise and focus on raising the most for your organization. Handouts, including an events value test and a checklist of set-it and forget-it ways to generate revenue for organizations of all sizes will be given to participants.
The takeaway is that every event—regardless of size—must earn its place by generating significant net revenue, promoting donor value, and aligning with the organization's strategic focus. If you can’t say that about your events, then it might be time to reposition your organization for success!
Using AI in Fundraising: Live Demos on Campaign Preparedness
This session will use utilize live demos of GenAI as a strategic thought partner in assessing campaign preparedness, including gift pyramids, campaign priorities, and other key components of campaign planning. Questions and audience participation are encouraged.
Why Should I Care?: What Fundraising in Silicon Valley Taught me About Inspiring Donors to Give in the Attention Economy
We’re living through an era of both more and less. More AI-generated content. More products. More competition. Fewer donors. Less attention. Less trust. As empathy among the general public wanes and information overload grows, it’s becoming harder to build credibility and connection with donors via traditional means.
“’Why Should I Care?’: What Fundraising in Silicon Valley Taught Me about Inspiring Donors to Give in the Attention Economy,” will cover how to build relationships with donors (and grow revenue) in the current climate of increased skepticism and competition for attention. It will cover how click rates, sponsored content, and AI misuse have eroded our trust in what we see and read, what that means for donor mindsets, and how leaders and development professionals can still elicit trust and buy-in in a time when it seems like everyone is selling something (including our data).
Session goals:
1. Attendees will understand what the Trust Recession and Attention Economy are, how they came to be, and implications for fundraising.
2. Attendees will learn the key strategies to employ to overcome increasing distrust (and diminished attention spans) among donors
3. Attendees will have a basic framework for leveraging these strategies within their major gifts and annual fund programs
4. Attendees will understand where employing AI can help build trust and enhance outcomes, and where it can erode it.
5. Attendees will leave with the tools to authentically connect with donors, so that they pay attention and invest in the mission.
Handout:
A 2-sided chart detailing where trust-building can be woven into common major gift and annual fund activities
Your Website is Part of Your Fundraising Strategy- Is it Doing its Job?
Your website’s home page is often the first stop for donors, sponsors, volunteers, event attendees, community partners, and others who want to understand your organization and decide what to do next. Good home page design is not just about appearance - it is about usability, clarity, trust, and helping people find the information they need.
In this practical session, we’ll talk about best practices for nonprofit home page and landing page design, how to identify the key audiences your website needs to serve, and how to think through the engagement pathways that guide visitors to other parts of your site. For fundraising professionals, this includes making sure supporters can quickly understand your mission, see your impact, and take meaningful next steps.
Participants will receive a simple website planning worksheet they can use to review a home page or landing page, identify gaps, and start more productive conversations with staff, leadership, or web partners. The session is designed for fundraising and communications professionals who want their website to better support donor engagement, storytelling, and organizational credibility without getting lost in technical jargon.
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