Funder Profile: Gail Gilbert Ball W’79

5 min readMar 8, 2022


Meet Gail Ball, Super Funder, VC and Entrepreneur

In our first Funder profile, WAFFA Board Member Gail Gilbert Ball tells how she broke into venture capital and shares invaluable advice for aspiring Founders. Gail talks about the pitch process and how important it is to “control the way someone hears your story” by leaving room for your listener while pitching. She recommends that you bring people along with you, and make it easier for them to identify with what you are saying and by the time you get to the Q&A portion, they won’t be throwing up challenges — rather they will be striving to contribute to your concept.

Gail is a member of multiple entrepreneurial, venture, and financial interest groups, including Hamilton Lane, Delaware Innovation Space, Silver Lining Finance and the Fulton Financial Group, just to name a few.

Gail’s been a fintech executive with a long career leading tech teams at global financial services firms. Building and overseeing a broad swath of entrepreneurial groups, she has held decision-making posts at nearly every seat around the financial services table — banking executive, regulator, service provider, and board member — in both for-profit and social-impact markets.

How did you break into venture capital?

I answered a LinkedIn job ad that a colleague sent me because of the Penn connection foremost and because venture capital was so much more exciting and expansive than what I had been doing inside even very innovative financial institutions.

If I had to say why I got the job over two men who were already in VC in VC cities? I had the same or better analysis, technical and operating skills. I also had a lifetime of rich engagement with the Penn and Wharton community as an alumni leader locally and on campus. The Penn network that came with that passionate, rewarding engagement gave me a leg up in fundraising and deal flow.

What is the last company you invested in and why?

The last company I invested in was also one of my earliest investments as an MP at Chestnut Street Ventures, Burrow. Last year, I was able to invest again, in my individual capacity, in their Series C as a syndicate member/investor with AV.

Do you have any advice for aspiring founders on how to create a persuasive and effective pitch deck?

Two distinct thoughts here that I believe in wholeheartedly singly and as complements to one another.

First, a twist on the adage to start with the end in mind. There is tons of research to evidence that controlling the Q&A in a pitch setting will materially change the likelihood and size of an investment.

How do you control the Q&A? You control the way someone hears your story before you get to the Q&A. How do you control how someone hears you? By being deliberate about where in your story they are invited to think alongside you. Do this well and you and they will look at the Q&A differently — not to throw up challenges, but to make contributions.

Someone once told me that you must always leave room in any conversation for others…even if you feel like you have the data that’s been missing, the answer to the question that everyone has been searching for and this is the moment the world has been waiting for!

From this comes the second message I share with founders.

Make room for your listener while you’re pitching. Structuring your story straightforwardly is the best way to ‘get’ by ‘giving’. To get what they have to offer (capital? connections? customers?) you need to structure what you’re saying so that you are bringing people along with you. Simple, important facts about your connection to this opportunity, recognizable statements of the problem, logical, reliably sourced estimates of the market, honest focus on what you don’t know yet….forget the slide design template and complicated graphics! Oh, the stories I could share!

If you bring them along with you by making it easy for them to identify with what you are saying, they will see for themselves the right spot to open up about their ideas and thinking and feel welcomed to share it with you….the way you want the relationship to continue when you win their interest.

I feel strongly about this from personal experience (failing to “make room” early on in my career) and observations (1000’s of pitches). Someone who wasn’t a venture capitalist but who described this communications and innovation strategy inspiringly? Ruth Bader Ginsburg who said, “Fight for the things that you care about, but do it in a way that will lead others to join you.” Over her long, impactful career, she did just that by taking the time to understand the perspectives and concerns of those that opposed her views, and then making powerful, logical arguments that spoke to them.

If you don’t leave room in the conversation to hear others’ views, you can’t persuade them to join you.

Tell us about a time when things went wrong with a founder/investment? What happened and what did you learn from it?

In my individual capacity, I joined the board and invested in an early stage company that within two years successfully raised a series seed from a global top tier fund focused in this sector. Disarray and disagreements among the old (friends and family) and new (fund) board members chewed up the better part of the next two years…instead of the acceleration expected.

What did I learn? Success…and failure….are always about the people and it’s not just the founding team, it’s about all the people who need to be aligned to realize the opportunity that everyone sees.

What is one piece of advice you consistently give to female founders? And last but not least…

Stories and great ideas are meant to be heard. Find the rooms you need to be in and tell your story while listening intently.

And last but not least…

A brilliant military academy grad and Wharton MBA, very successfully investing in the pre seed and seed stage, once told me that “helping was the best form of due diligence” and I couldn’t agree more.

At AV, where we were always co-investors, never leading, we needed founder advocacy to help us get into deals and so helping was in our DNA.

I think I was kind of born this way, and I suspect that part of the reason why I found Penn such a meaningful experience is the challenge to “Be Like Ben” and ask myself the question attributed to Ben Franklin at the end of every day’s PennToday newsletter: “The noblest question in the world is: What good may I do in it?

Interested in a deeper dive? In 2020 Gail sat down with WAFFA in SF for a candid conversation. She discusses some of the mistakes she sees female founders make when fundraising, what the VCs say about you when you’ve left the pitch room, and where confidence comes from and how to get more of it.

Connect with Gail here!




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