Fast Forward's 2025 Alumni Retreat Recap

Another year, another gathering of nonprofit leaders pushing the boundaries of tech for good. The 2025 Fast Forward Alumni Retreat brought together some of the brightest minds at The Golden Gate Club in San Francisco in January. Over two days, nonprofit leaders, technologists, and funders met to talk shop, swap strategies, and address the challenges shaping the sector.

Between coffee-fueled brainstorming sessions and candid hallway conversations, we explored the big questions keeping nonprofit leaders up at night: How do you fundraise when budgets are tightening? Where can you find top-tier tech talent without Silicon Valley salaries? And how do you make AI work for your mission?

Inside this recap, you'll find the sharpest insights from this year’s retreat: practical strategies, memorable quotes, and real-world solutions tailored to the unique challenges of nonprofit innovators in 2025. We’ve skipped the buzzwords and empty platitudes to focus on what actually works: funding strategies that cut through the noise, leadership structures that foster growth, and AI tools that enhance your mission without adding risk.

No fluff, no filler — just the best of the best from this year’s retreat.

From Founder to Leader

Building a Leadership Team That Actually Works

When do you know when it’s time to build out your leadership team? If you’re a nonprofit founder or ED, the answer probably falls somewhere between “yesterday” and “I have no idea.” Growing your leadership team isn’t just about hiring. It’s about structuring leadership in a way that actually works for your organization. At the 2025 Alumni Retreat, nonprofit leaders swapped lessons on when (and how) to expand their teams, building on insights from experts like The Bridgespan Group, whose research has shaped best practices in nonprofit leadership. There’s no magic formula. But here’s what attendees agreed on:

Your sign that it’s time to expand:

• The CEO is drowning in decisions someone else could handle.

• High-stakes problems require input from multiple teams.

• There’s a glaring lack of representation in decision-making.

Most organizations found that a leadership team of two to six people hits the sweet spot. It’s big enough for diversity of thought, small enough to avoid “this meeting could have been an email” syndrome.

But success isn’t just about hiring. It’s about structuring leadership to work for your organization. Build a structure that fits your organization's size, mission, and culture. Not what you think a leadership team should look like.

Some key takeaways:

Meet less, but make it count. Long, frequent leadership meetings drain time. Instead, focus on high-stakes, cross-functional decisions and keep the agenda tight.

Clarify the purpose of every agenda item. Is it for discussion? A decision? Strategy alignment? Being explicit helps cut through the noise.

Delegate like you mean it. Leadership teams that scale well know when to delegate — not every decision needs to go through the CEO.

The bottom line: The best leadership teams don’t just exist on an organizational chart. They’re intentional, structured for growth, and designed to help an organization thrive. For a deeper dive into effective leadership structures, check out Five Tips To Supercharge Your Leadership Team from The Bridgespan Group.

The Chief of Staff: Your Right-Hand Strategist

If you think a chief of staff is just an over-glorified executive assistant, think again. They’re the glue between leadership and operations, making sure priorities don’t get lost in the day-to-day whirlwind of running a fast-growing tech nonprofit. This was a hot topic at the 2025 Alumni Retreat, where Claire Beiler (Lemontree), Kasumi Quinlan (Lemontree), Jared Chung (Career Village), YoonJi Kim (CareerVillage), and Jono McKay (SameSame Collective) led a discussion on what makes a great chief of staff.

Jared Chung (CareerVillage), YoonJi Kim (CareerVillage), and Jono McKay (SameSame)

According to attendees, here’s what makes a great chief of staff:

• Seeing around corners: The best chiefs of staff anticipate challenges before they become a full-blown crisis.

Example: As one AI-powered nonprofit grew, its chief of staff identified operational bottlenecks before they became obstacles. By identifying which processes could be automated or delegated early on, they kept the team moving at full speed without overloading leadership.

• Turning chaos into clarity: Managing complex projects across teams can be messy. A chief of staff keeps teams aligned and leadership out of the weeds.

Example: One retreat attendee shared how their chief of staff implemented a weekly leadership sync focused on top priorities and blockers. This dramatically reduced last-minute fire drills and freed up the executive team for high-impact work.

• Balancing long-term vision with immediate execution: A great chief of staff makes sure leadership isn’t just reacting to what’s in front of them, but also laying the groundwork for what’s next.

Example: When a nonprofit launched a high-stakes partnership, their chief of staff broke down the complex, multi-stakeholder deal into clear phases, ensuring smooth collaboration across program teams, funders, and leadership. They made it make sense.

For many nonprofits, hiring a chief of staff was a “wish we had done this sooner” moment. Having someone dedicated to internal alignment and executive priorities freed up CEOs to actually lead rather than get stuck in decision overload. If you’re feeling stretched thin, it might be time to bring in a chief of staff to help turn big ideas into action. And perhaps more importantly, keep your leadership team from drowning in logistics.

Are You Ready for a Chief of Staff?

If you check three or more of these boxes, it might be time:

☐ You’re the bottleneck for too many decisions.
☐ Your calendar is a graveyard of meetings with no prep time.
☐ Big ideas get discussed but rarely make it past the whiteboard.
☐ You’re constantly putting out fires instead of planning for the future.
☐ You wish you had a strategic thought partner. 

If this list is hitting a little too close to home, a chief of staff could be the missing piece to help your team run more smoothly and free you up to focus on what matters most. (Your mission!)

Building a Personal Brand

If you don’t shape your brand, someone else will do it for you. In today’s digital world, nonprofit leaders can’t just sit back and hope people get the right impression. Whether you’re speaking directly to donors, positioning yourself as a thought leader, or amplifying your organization’s work, a strong personal brand is a strategic asset.

At the 2025 Alumni Retreat, founders and nonprofit leaders got candid about their experiences building (and sometimes struggling with) personal brands. Leaders like Jehron Petty (ColorStack), Tiffany Green (Uprooted Academy), and Jared Walker (Dollar For) offered strategies that make it easier to stay consistent without it becoming a full-time job.

Jared Walker (Dollar For), Jehron Petty (ColorStack), Tiffany Green (Uprooted Academy), Nicole Dunn (Fast Forward)

Here’s what we learned:

Why Personal Branding Matters

Donors, partners, and the broader community are more likely to engage with your nonprofit if they trust and connect with YOU as a leader. A well-crafted personal brand can:

• Establish credibility and authority in your field.

• Build authentic relationships with donors and funders.

• Keep your organization top-of-mind in a noisy digital landscape.

• Strengthen your ability to drive meaningful conversations and change.

Finding Your Voice Without Feeling Cringe

Let’s address the elephant in the room: posting online can feel weird. Many founders hesitate to share their thoughts publicly, worried about coming across as self-promotional, taking too much time, or saying the wrong thing. The key? Find an approach that feels authentic. Yes, it can be done.

Pick a platform that aligns with your goals. If your audience is funders and donors, LinkedIn is likely your best bet. If you’re speaking to young users or community members, Instagram or TikTok may be more effective.

Write how you talk. You don’t need to sound like a press release. Keep it conversational and natural.

Start small. You don’t need to post every day. Sharing insights, behind-the-scenes moments, or reactions to relevant articles once a week is a good starting point.

Engage, don’t just broadcast. Comment on other people’s posts, share relevant content, and join the conversation.

Think before you post. If it’s not appropriate to share WIDELY, don’t post it.

Strategies for Building an Engaging Presence

1. Post with Intention

Instead of overwhelming yourself with daily content, set a cadence that works for you. Many nonprofit leaders at the retreat recommended:

• 2-3 high-value posts per week. These could be insights on your work, reflections on industry trends, or highlights of your nonprofit’s impact.

• Daily quick posts on Stories (if using Instagram or Facebook). Behind-the-scenes moments, speaking engagements, or short updates can keep people engaged without requiring high production value.

2. Make It Easy: Templates & Time Blocking

• Jehron Petty (ColorStack) uses content templates to speed up the process.

• Tiffany Green (Uprooted Academy) time-blocks 90 minutes every Friday to batch her LinkedIn posts for the week.

• Jared Walker (Dollar For) dedicates 4 hours weekly to creating and editing videos.

3. Leverage Your Network

• Let your team and supporters know when you post so they can engage.

• Don’t be afraid to ask for likes, shares, and comments — it’s how algorithms work!

• Cross-promote your content across different channels to maximize reach.

4. Balance Your Personal Brand with Your Organization’s Brand

Your personal brand should complement, not compete with, your nonprofit’s identity. The goal is to elevate your mission while allowing people to connect with the leader behind the work.

5. Overcoming Fear & Avoiding Burnout

• Fear of judgment? Not every post has to be perfect. Social media is about connection, not perfection. Focus on authenticity over flawlessness. Your audience will appreciate your perspective more than polished perfection.

• Worried about time? Save it by planning ahead. Batch-create content, schedule posts in advance, and repurpose ideas across different formats. (Evergreen content, baby!) A single thought can turn into multiple posts with small tweaks.

• Not sure what to say? Start simple. React to industry news, share small wins, highlight team members, or offer a behind-the-scenes look at your work.

Personal branding isn’t about self-promotion. It’s about making sure your story is told the way you want it to be. Whether you’re securing funding, building a movement, or shaping public opinion, your voice is a powerful tool.

Remember: If you don’t shape your brand, someone else will do it for you. Take the reins, be intentional, and let your digital presence work for your mission.

AI + Product

AI Basics: What Nonprofits Need to Know

At the 2025 Alumni Retreat, nonprofit leaders explored the fundamentals of AI. Addie Achan, Fast Forward’s director of AI programs broke down key technologies, development processes, and ethical considerations. This section covers the essential AI concepts every nonprofit should know, plus the latest discussions on reasoning models, agentic AI, and ethical challenges.

Whether you're just starting to experiment with AI or looking to deepen your knowledge, these insights will help you navigate this rapidly evolving landscape with confidence.

Addie Achan (Fast Forward)

Foundational Concepts

Artificial Intelligence (AI): Technology that enables machines to simulate human intelligence.

Machine Learning (ML): A branch of AI focused on computer systems learning patterns from data.

Neural Network: A computational model inspired by the human brain.

Deep Learning: A subset of ML that uses neural networks to learn complex patterns from data.

Key AI Technologies

Natural Language Processing (NLP): A field of AI focused on understanding human language.

Generative AI (GenAI): A type of AI that is capable of creating new content.

Large Language Model (LLM): A massive AI system that understands and creates language.

Agentic AI: Autonomous AI capable of independent action without continuous human oversight.

AI Development and Implementation

Training: The process by which an AI model learns to perform tasks by exposing it to data.

Fine-tuning: The adaptation or refinement of an existing model for a specific task or domain.

Prompt Engineering: The crafting and refining of instructions given to LLMs to guide their outputs.

AI Considerations

Hallucination: An instance when an AI model produces false or misleading information.

Bias: Systematic favoritism in AI outputs caused by skewed data or flawed algorithms.

Data Governance: The practice of responsibly managing the collection, use, and protection of data.

AI Ethics: The moral principles guiding the development and deployment of AI.

Additional AI Concepts Discussed at the Retreat

Reasoning Models: Unlike basic AI that spits out quick answers, reasoning models think before responding, improving accuracy and reducing hallucinations. Translation: Less nonsense, more useful insights.

Ethical AI: The big three concerns: bias, misinformation, and oversight. AI can be a game-changer, but if it’s trained on flawed data, it can reinforce inequalities. Keeping humans in the loop is non-negotiable.

AI in Action: How Nonprofits Are Making It Work

AI is everywhere. But how do you actually use it in a way that helps your nonprofit rather than adding to the chaos? At the retreat, nonprofit leaders shared real-world ways they’re putting AI to work without losing sight of their mission.

Keeping AI Accountable: Mental health nonprofit Koko partners with Compass Ethics, an external AI ethics board, to keep their AI-powered support tools aligned with best practices. This ensures their tech stays responsible and human-centered.

Human-in-the-Loop Models That Work: Empower Work empowers their human peer counselors with AI, including an AI assistant that offers next response suggestions, relevant resource recommendations, and quick conversation summaries. The extra layer of support helps counselors when they need it most — whether they’re feeling stuck, handling a complex situation, or aiming to assist more help seekers efficiently, all while keeping the conversation personal and human-centered.

AI-Powered Grant Writing That Saves Time: Free Our Vote sped up their grant writing process by incorporating AI into their workflow. Instead of spending hours formatting and structuring applications, their team now focuses on storytelling and strategy — letting AI handle the busywork.

The big takeaway? AI isn’t a magic fix. The best implementations pair automation with human oversight, ensuring AI serves the mission. Not the other way around. Need a guide to do it right? Check out Fast Forward’s Nonprofit AI Policy Builder.

Fundraising & Partnerships

Securing the Bag in Uncertain Times

Funding has always been a moving target, but in 2025, the shifts are happening faster than ever. With economic slowdowns, shifting political climates, and evolving funder priorities, nonprofit leaders are getting creative to keep the lights on — and their missions thriving.

Adapting to Shifting Funding Priorities

One of the biggest takeaways from this year’s retreat? Nonprofits that thrive are the ones that adapt. Funders are adjusting their priorities in response to new political and economic realities, and organizations that can frame their work in ways that align with these shifts are better positioned for long-term sustainability.

So, what’s working?

Reframing the Narrative: The work itself may not change, but the way you talk about it should. Several nonprofits shared how they’ve successfully repositioned their programs to better align with funder priorities. The mission stays the same, but the messaging evolves.

Building Funders into the Process: The days of cold grant applications and one-off donations are fading. The nonprofits seeing the most success are treating funders like thought partners — inviting them into the work, co-designing solutions, and keeping them engaged beyond the grant cycle.

Making Multi-Year Funding the Norm: One of the most valuable (and underused) fundraising tactics? Asking for multi-year commitments. Instead of scrambling for funding year after year, organizations that directly request multi-year grants are creating financial stability and spending less time chasing dollars. Pro tip: Many funders are open to the idea — they just need to be asked.

How to Make Your AI Proposal Stand Out

Imagine submitting an AI proposal requesting $1M in funding. It lands on a grantmaker’s desk, and they need to determine if it’s worth investing in. How do they evaluate it? Grantmakers are looking for clarity, feasibility, and long-term impact. A strong proposal anticipates their key questions and provides compelling, well-supported answers. Below are common questions from funders and what they expect to see in a winning submission.

Problem & Impact

• Is AI the right solution? Show a clear problem statement, data-driven impact metrics, and why AI is the best fit.

• Did beneficiaries provide input? Highlight surveys, user testing, and ongoing feedback to refine AI solutions.

• What external factors support growth? Address policy shifts, tech advancements, key partnerships, and market trends.

Capacity & Resources

• Does the team have the right skills? Outline expertise, gaps, and plans to hire, train, or outsource.

• Are partnerships leveraged? Mention collaborations for tech access, secondment programs, and go-to-market strategies.

• Does the budget reflect realistic costs? Detail scaling expenses, cloud storage, model updates, and talent acquisition.

• Is there a revenue model? Describe earned revenue, sustainability plans, and long-term funding strategies.

Data & Technical Approach

• How will costs be managed? Use open-source tools, lean development, and community-driven feedback.

• Is data handled ethically? Link to AI/data policies and outline responsible data use.

• How will privacy be protected? Align with best practices, ensure compliance, and implement oversight.

• What testing methods limit bias? Explain performance evaluations, bias mitigation, and human oversight.

Ethical Considerations

• What are the risks? Address privacy concerns, job displacement, and unintended biases with clear mitigation strategies.

• Are long-term impacts considered? Outline second and third-order effects of success or failure.

• Is AI transparency prioritized? Include clear disclosures, user education, and privacy policies.