Fearlessly Innovative: Navigating Enterprise EdTech and Venture Capital

4 min readJan 13, 2021

This post is part of BenchK12’s The Playbook, a quarterly update shared with those interested in K12 education, Enterprise/Edtech/Future of Work startups, and women-founded companies. Follow or subscribe for more.

Working in San Francisco for nearly 20 years, I can honestly say that it is well on its way to becoming an automated city. Robot baristas, food, private transport, and personal assistants are all available at the click of a button. Since the onset of COVID-19, our daily existence has become more and more digitized with Zoom weddings and happy hours.

Although I have lived and worked in the Bay Area within startups and Tech, I’ve never jumped into “big tech,”; instead I’ve enjoyed working with small businesses, individuals, nonprofits, and artists — people with a whole lot of passion but limited funds. It was 100% bootstrap, 100% of the time, far beyond the glowing beacon of the Salesforce Tower. This experience has made me very tech agnostic in a land where people wear tech affiliation lanyards and embroidered hoodies like sports team jerseys or military uniforms. (Ironically, I can’t wait to have our own BenchK12 swag when the time is right!)

In the last seven months, as most of the city’s inhabitants have spent time locked away at home doing our best to flatten the curve, I’ve spent my time reading copious amounts of sci-fi and diving headlong into the world of K12 edtech. This pairing of activities became oddly fitting as I am very much an alien in this education landscape, trying to explore and take in as much as I can.

There are many aspects of this realm that feel foreign: the large, lumbering structures deeply rooted in legacy systems, their operational functions that very much are performed with hands, paper, and telephony(?!) — like an enduring time capsule. The great technological tidal waves of the past few decades have barely breached the walls of K12, where they could be the most helpful in expanding the capacity of those providing such a critical service to our communities and nation. To the uninitiated, this is because the education sector lacks innovation and clings to the status quo. However, in my short time working in the education sector, I’m less convinced of that; maybe it’s actually Tech that needs a shake up to work in education.

I came to this conclusion based on BenchK12’s participation in two virtual incubators and early pitch meetings in the latter half of 2020. As we worked our way through YCombinator’s StartUp School and HMC Inq the velocity and bootstrap nature of being a part of a startup in an incubator fit like an old glove. However, the world of venture capital (VC) funding, something which seems to make or break enterprise startups, was yet more new territory to be navigated.

While we prepared for our pitch meetings, researching investment partners, building our pitch deck, doing practice rounds with our peers and mentors, we grew increasingly confident. We were getting great feedback — our problem and solution is clear, we are significantly different from our competition, there is a large market waiting for this kind of help, and our team can deliver. But after a few investor meetings we began to realize that tech advances haven’t reached education because while most investors like a “moat,” they don’t like islands (unless they’re buying them…😉). And the education sector is like an impenetrable island to many investors.

The nice thing about living on an island is that you don’t need a moat. This is both the incredibly amazing and difficult thing about the education sector and why so many VCs will fund “enterprise,” but not “edtech enterprise.” When the industry mantra is “move fast and break things,” and you want billion dollar exits in five years, the structures and culture of public sector educational institutions seem to run into conflict with those goals. So how do we change that? How do we bring all of the good that Tech can do to the education sector, while respecting and serving the critically important expertise that educators have and bring to their work every day?

This is exactly why I got involved with BenchK12. I see the spark, knowledge, and expertise my co-founder, Brooke, possesses for not only improving the data landscape of K12, but also the passion she holds for championing the future of work in the educational space. Her drive and insights are precisely what I would dream about in a successful business partnership. Together, we know that we’re building more than a product, we want to build the ship that links the best that technology has to offer, with the future generations of leaders and innovators who are in our classrooms today.

As we are bringing BenchK12 to life and learning how to navigate these waters, we have our eyes on the horizon of how emerging technologies can support outcomes for students while empowering and strengthening its workforce — and I’m excited to share more about that with you in future posts. But in this moment, we need the innovative disruptors that Tech is known for producing to be less fearful of the education sector and join our team of capable, fearless tech visionaries on this journey to elevate and serve K12 education with the best that Tech has to offer. All aboard!




Creative at heart, designer/developer by trade, and community builder by nature.