Focus on Fundraising

What I Wish I Knew as an Early-Career Major Gift Officer

Simple concepts, paired with reps, builds confidence and effectiveness

By Jason Penry, Ph.D. | September 15, 2026

Monthly Column

Focus on Fundraising

On the third Tuesday of each month, Penry’s column, “Focus on Fundraising,” delivers actionable insights into major gift trends and strategies within college athletics.

The lifeblood of any development program is its pipeline, yet the important task of uncovering new major gift donors frequently falls upon the shoulders of early-career fundraisers.

While discovery and qualification work forms the foundation of any successful development program, it remains one of the most demanding, unglamorous, and technically demanding jobs in the industry. For entry-level major gift officers, navigating this initial phase of their career is an incredibly tough proving ground, one where high expectations meet a steep learning curve.

My first role in major gift fundraising was easily the hardest of my career. Looking back, I was inexperienced, lacked confidence, and was only in my mid-20s. On top of that, I had the weakest portfolio on the team. Securing appointments felt nearly impossible, let alone actually raising money. I am not sharing this as an excuse, but as a candid look at how brutal the starting line can be.

Some training programs completely overwhelm new gift officers with an excess of strategies. Early career fundraisers do not need complexity, they need a simple understanding of what really matters, reps, discipline, and the confidence that comes from doing. Through my own 20 years in the field and my consulting work, I have found one undeniable truth: simple wins in fundraising.

This article distills the core insights I wish I’d possessed when I started. These topics represent a curated selection from my personalized workshop for clients, Major Gift Fundraising Academy: A Practical Refresher on Fundamentals.

The Rookie Mindset

Embrace Reality

When I started as a gift officer, I battled imposter syndrome. I suspect a lot of young fundraisers do, even if they don't admit it. The reality is that as an early-career gift officer, you simply do not have the reps, experience, or portfolio, to deliver superstar numbers yet. Take a breath and relax.

The reality is that as an early-career gift officer, you simply do not have the reps, experience, or portfolio to deliver superstar numbers yet. Take a breath and relax.

Your greatest value to an athletic department is in discovery work: bringing "new" major gift donors to the table. That is hard work, and there is no easy button. Push through these early years to secure reps and develop a personal style and rhythm that works for you.

Just Be Yourself

In 2008, I asked Mike Holder, the highly effective athletic director at Oklahoma State, what made a great fundraiser. I deeply admired Mike as he raised more money than any other athletic director in the history of college athletics.

He looked at me and replied, “Just be yourself.”

“Just be yourself.”

His point was simple: when you come across as genuine, people trust you. If they trust you, you can build a relationship. If you can build a relationship, you can be a great fundraiser. Many new professionals completely overthink the craft. Throw out the mechanical script and just be yourself.

The Activity Blueprint

Control the Controllables

Early on, I feared metrics. Eventually, I learned to embrace dashboards because they keep us accountable and provide much-needed structure. They also signal to leadership when you are off track and need support.

When I moved into leadership, I frequently repeated this rule: your goals for visits and asks are controllable and non-negotiable. If a fundraiser missed their dollars raised goal but hit their activity metrics, I was understanding. Total dollars raised can only be influenced, never completely controlled.

Don't obsess over dollars. Obsess over the activities that create dollars.

Don't obsess over dollars. Obsess over the activities that create dollars. You cannot control exactly how much someone gives today. You can control how many people you meet, how many relationships you develop, how many proposals you make, and how many gift decisions you secure.

Tier Your Portfolio

As an early-career professional, you will likely be handed a large, unwieldy donor portfolio. It can feel completely overwhelming. Remember that your portfolio is not created equally. Prioritize your list into at least three or four distinct tiers, and aggressively protect your schedule to spend face-time with your most important prospects.

The Mechanics of the Work

Expect Ghosting

You will be ghosted. Do not take it personally, it is not about you. In discovery work, attempting to contact a prospect ten or more times before getting a response is more common than uncommon. Err heavily on the side of persistence. Many of today’s top athletic donors are the direct result of a veteran fundraiser’s relentless outreach years prior.

See People

If you fail at everything and only succeed at one thing as a development professional: see people! This is as close to a magic pill as there is in fundraising.

If you fail at everything and only succeed at one thing as a development professional: see people! This is as close to a magic pill as there is in fundraising.

The best donor research is done across a table, not on a computer screen. Ask good questions and be an elite listener. On my first visit with a prospect, my favorite, go-to question: “Where did you grow up?”

Our values are deeply shaped early in life. Understanding a donor's rural versus urban upbringing adds immediate clarity to what may drive them. When donors tell their early life stories, I am always amazed by how much I learn about what they care about today and how I might tie it to a compelling fundraising project.

Drive Cultivation Through Connection

Involvement precedes investment, almost always.

Involvement precedes investment, almost always. Find a creative way to get your prospects physically connected to the program. While there are dozens of strategies in a major gift officer's engagement toolkit, the most effective tool has often been a campus visit. When individuals and couples visit campus to meet with the athletic director, coaches, or student-athletes, the odds of a major gift skyrocket.

Driving Decisions

Secure the "Yes, No, or Maybe"

As my mentor taught me, our professional obligation as major gift officers is simply to secure gift decisions: yes, no, or maybe. A fundraising professional who can consistently secure decisions is incredibly valuable.

To this day, I love when people ask why I funded my very first endowed scholarship, which I am very proud of. The answer isn't complex: a gift officer had the courage to ask me.

The more you ask, the sharper your skills become. Don't be afraid to crawl before you walk. Your job isn't to force everyone to say yes. Your job is to help donors arrive at a gift decision.

Your job isn't to force everyone to say yes. Your job is to help donors arrive to a gift decision.

Urgency vs. Desperation

The pressure to raise money in the modern era of college athletics is intense, requiring a careful balancing act. You must lean toward being aggressive, but not too aggressive. The moment a donor feels like they are viewed as a walking ATM, they shut down and the relationship sours instantly.

The Bottom Line

Have an aggressive bias to action. Your success as an early career major gift fundraiser is a matter of discipline and consistency, not genius. Let go of any emotional attachment to outcomes, such as gifts secured, and focus entirely on the controllable.

As my greatest mentor, Stu Starner, repeatedly taught his fundraisers:

"Daily processes, worked diligently, over a period of time, will inevitably achieve success."

Summary

You don't need to be a superstar on day one. You just need reps.

Make the call, send the text, send the email. Do whatever it takes. Secure the appointment.

Get in the car. See people. See people. See more people. Listen. Ask.

Do it again tomorrow.

That is exactly how major gift fundraisers are built. There are no shortcuts.

About the Author

Jason Penry, Ph.D.

Dr. Jason Penry has over 20 years of experience in consulting. His firm, Penry Advisors, provides Group of 6 and FCS-level leaders with the structure, strategic guidance, and confidence to unlock greater major gift potential in an ever-changing college athletics landscape.

Penry was the second-ever holder of the James W. Aston ’33 University Chair in Institutional Development, established in 1985, at Texas A&M University. He spent over a decade in university leadership as the chief advancement officer at two other universities: Angelo State University in the Texas Tech System and Arkansas State University.

Driven by a collaborative, team-first approach, Penry successfully engineered record-breaking fundraising years in 11 of his 13 years in philanthropic leadership roles.

External Contributor

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