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Meet Courtney

Key Quotes

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

Experiences Shaping My Investment Approach

I have always been motivated in my career by what I did and who I did it with and for.  When I started thinking about venture, it was less borne of a specific desire to be a career investor or to have my own fund, and more of a conviction that venture was the right vehicle to get exposure to a transformational social and demographic transition.  I’m really lucky that I usually managed to get myself in the right place at the right time in my career.  I joined Goldman just as capital markets entered a period of monumental transition from a tech standpoint; I followed a Goldman exec to the NYSE and got to work on revolutionizing that storied institution from a non-profit to a for-profit and then to IPO via a historic M&A transaction.  Later, I joined Marsh, the world’s largest insurance broker, right at the dawn of the insurtech trends. Through it all, I’ve followed my nose to things that looked a bit squirrely or non-obvious but seemed like they’d be pretty interesting, and thankfully, I was usually right.  

Starting Springbank was similar.  It felt like we were on the edge of an unprecedented social and demographic transition that had women at the center. Yet, the most powerful engine of innovation was not building with them in mind.  We can have Doritos in minutes but we can’t find daycare to save our lives. And yet, women make up a larger share of the workforce than ever — and growing; women are the dominant paid and unpaid caregivers for a population that is careening expensively into old age; women will inherit over $100 trillion in the next decade, and their investment priorities are decidedly different from men’s; women graduate college at a rate significantly higher than men; women control 80% of household spending; and on and on. And so I just had a hunch that with all this change, there would be some interesting opportunities to build into this massive transition.

Moment Inspiring Venture Capital Career

It was 2016/17—I was still Marsh's CFO.  We went on a visiting tour of the major VC funds out in the Valley, and that opened my eyes to “little tech” and “little finance,” whereas until then, I had only been exposed to large-scale fintech and the biggest capital stage there was—the NYSE.  About a year later, Silicon Valley's lack of female founders and check-writers exploded as a headline issue.  At first, it surprised me a bit — there is an underrepresentation of women across the economy, so why did this hit such a nerve in the public discourse? It was because the VC ecosystem in the US is so strong and powerful that it essentially gets to decide what problems are worth solving. Without women at the table, we were missing some pretty important problems.  That really stuck with me, and I came to believe that our innovation engine needed to start working on the problems that affected women as the end user—building the infrastructure that is missing for them—and that starting Springbank was a way that I could contribute to that.

Influences on My Worldview

I’ve been fortunate to be on incredible teams in my life and career. From youth swimming to my college lacrosse team, I always played team sports. I immediately went into a career where I worked with a handful of awesome bosses and mentors who built strong teams. They also focused on doing business the right way — guided by a strong sense of doing the right thing for the right reason, being long-term greedy, negotiating fairly, and emphasizing the criticality of trust and relationships. I am passionate about the power of teams, the value of debate and hard work, and the need to pick each other up after inevitable mistakes. All of this leads me to a very team-oriented approach to decision-making, which requires highly structured thinking and putting the key points to paper so that we can baseline everyone with the same info and get the most out of the team’s effort and collective brain.

Unconventional Belief

It may sound provocative, but we often say one of the unconventional things we do is take women seriously as founders, buyers, and customers of services.  It’s pretty well-documented that many investors do not.  But we know that women are moving into the workforce, into wealth, and positions of societal power at an astounding rate compared to historical precedent — even if it still feels not fast enough.  Women are not “little men,” as we have learned in everything from drug testing to car safety testing, and there will be a huge economic opportunity that will come from viewing the world through their eyes and building infrastructure that enables society to serve them better.

Balancing Intuition with Data

The answer is always both, I’m sure, for all investors.  I am fascinated by the subconscious as an extracurricular pursuit — I think the things we don’t know (consciously) that we see are powerful contributors to our behavior and influence our decisions.  So, I weigh intuition heavily, but it’s usually the thing that will STOP me from doing a deal more than the thing that makes me do a deal.  To DO a deal, I am, first and foremost, data-driven. I focus heavily on the business model and incentive systems that work for or against a buyer’s reason to adopt.  To be honest, I worry less about the specific math or data around TAM — we get paid to take market-creation bets.

Best Advice Received

Right after I started my job at Goldman, I got moved (by random selection, not by choice) from the M&A department in the investment bank to a trading firm that Goldman had acquired.  It took me out of an advisory role and into an operating business overnight.  At first, I thought about quitting and going to a different firm, but one of my bank mentors told me to try it — that it would be valuable to learn how a business is actually run from the inside.  I took her advice, and it changed everything for me. I spent the next 16 years in operating jobs across financial services companies.  As an investor, it is so valuable to have been inside of companies, understanding the daily grind of running a business, having an appreciation of all the stuff that goes wrong daily, and the highs that come when things go right.  Working inside companies for all those years before starting Springbank, I saw it all: hiring, firing, successful M&A, flawed due diligence, shareholder lawsuits, employees with health issues, tech implementations gone wrong, successful IPOs, tense board meetings, and people who some thought were “not ready” actually step up and smash it out of the park.  All of this experience is invaluable to me in my job today, and I never would have started down that path if my mentor hadn’t pushed me to. 

Philosophy and Insights

Investment Philosophy

I’m looking for deep founder expertise + a “root cause problem” being addressed.  I want an expert founder who knows their space well and all the challenges worth solving. This gives them the staying power needed to build a successful business.  I’m not a “I’ll back them building anything” type of investor.  I want a founder who breathes and eats the data about their market.  And what I mean by a “root cause problem” is that there’s limited money and attention span in the real world. In older industries or less innovative sectors in particular, figuring out what can be improved doesn’t earn you a medal — that’s the easy part. Figuring out what people are incentivized to change and capable of fixing creates a lasting solution.

Values When Working with Founders

Integrity above all.  There are 100 decisions to be made every day, so I need to feel really good about a founder’s integrity, long-term greed, transparency, and willingness to do the hard thing.  That’s true for all decisions I make about who to work with, and even more critical in many of the spaces that we invest in that can be delicate like healthcare or financial services.

The Perfect Founder Pitch

The perfect pitch is a walk with a cup of tea, where I leave the conversation with a strong personal connection, a clear understanding of the founder’s motivation, and blown away by their degree of knowledge of their numbers and powerful intuition about how their target market works. I also leave with a simple understanding of their solution, whose adoption feels inevitable to me.

Approach to Risk

Risk selection is the work of venture capital — and I would argue many other jobs as well.  Being the decider in any role is about choosing which risks you’re willing to take and which you aren’t.  We invest at the very early stages — typically pre-seed and seed — so there is risk everywhere.  Our diligence process tries to at least fully explore what’s knowable about a founder’s past experience and the market and buyer they’re going after because that knowable risk is the dumbest type of risk to take since you don’t have to.  The risk that I am the most excited to take, because it often has the biggest reward, is market creation risk.  We aren’t sure if there’s a market for a new insurance product or a new medical device or a new tool for teachers because no one has ever built it before — it’s not a slightly better mousetrap, it’s something that doesn’t exist.  Those are the biggest swings and can be the most fun. That said, in the name of balancing risk across the portfolio, not every investment can have that type of risk.

Measuring Success Beyond Returns

The expression goes, “Life is short,” but I live by the opposite mantra in my career: “Life is long.”  Success for me is using VC to bring more of the innovation engine to bear on some of our most significant social challenges.  If we enable more people to build life-changing solutions for women in particular, that will be as important to me as the returns we deliver to our investors.  And if we can do that so that everyone we work with — from our teammates to our co-investors to our founders — would work with us again, that’s the trifecta!

Trends and Future Vision

Exciting Trends and Technologies

I am excited about the potential for data to improve women’s health.  There are so many conditions that impact women differently or disproportionately, and for which we have had such limited data for years. Women’s bodies are complex because of the hormone cycle, and instead of embracing that complexity as a rich data set to learn from, we’ve excluded women from trials because of the “noise” that cycle creates.  I’m excited about companies like LevelZero, which we just invested in, that is using cutting-edge DNA aptamer technology to create a tool for continuous hormone monitoring — similar to a continuous glucose monitor — which could lead to incredible breakthroughs in diagnosing and treating women’s health issues and improving hormone visibility for both men and women.

Misconception About VCs

I think there’s the narrative of the brilliant lone wolf investor who sees around corners, driving innovation.  My experience of venture is that it’s much more of a team sport.  Venture has to work closely with “the real world” to understand when the time is right for new tech and innovative business models.  And the VC ecosystem has to work together. Very few funds are big enough on their own to support the full capital journey of a company.  So, I like to say that we need to see things before other people — but not too far before them because we need others to buy into the company and the vision and follow along.

Improving the VC Ecosystem

The US VC industry is one of the country's great assets.  It can support risk taking, testing, and pushing the limits of what’s possible in a way that most other countries can only dream of.  That said, I think it’s still pointed at too narrow a slice of our economy.  There are massive opportunities to build beyond white-collar workers, or beyond other start-ups as customers, or beyond just driving more consumption.  A wider variety of voices and more investors with real-world experience in more mainstream parts of our economy would be great to add.

Challenges for Early-Stage Founders

I think we’ve recently entered a bit more of a “risk off” stance given the volatility of the macro environment, high interest rates, and the lack of IPOs which breaks the liquidity cycle for venture that is needed to keep the dollars flowing.  So I think founders, in general, are facing tighter financing markets, and they should be.  In times like these, I think founders who don’t fit the typical Silicon Valley mold will struggle the most.  As VCs, we can be honest with founders about what they need to “fix” about their team, valuation, or model to be a venture-backable company and not just give them some happy talk, a vague rejection, and send them on their way.  This is the moment to lean into quality and invest not just in our portfolios but in the ecosystem's health overall.