Joining the On Deck Team

I joined On Deck to grow the Access Fund. On Deck is building a "modern education institution" where top talent and ambitious builders go to start or join a company, develop new skills, and build relationships. On Deck takes the “university bundle” — education, network, community, credentials — and applies it to the entire lifecycle of a person’s career. We’re building it native to the internet to remain fully global, accessible, and enduring.

The motivating idea behind the Access Fund is to take our obsession with unlocking potential to the limit. It ensures that extraordinary people encountering financial barriers can join the On Deck community. The Access Fund launched following the leadership of many former On Deck fellows. They approached the team to share how transformative the cohort experience had been for them, and they wanted to sponsor future fellows who have the talent and tenacity to launch a company but lack the typical background and/or resources founders today often have.

Meeting On Deck

In March 2020, at the very beginning of the pandemic, I was assigned a project outside of my day-to-day role as an Executive Director at Teach For America. Elisa, TFA's CEO, called and asked me to lead a process to assess the different answers and implications to a big question: should TFA bring in its 2020 cohort of 2500 new teachers? I had a week to mobilize leaders across the organization to explore different paths, identify and weigh the risk factors, and propose a path forward for Elisa's consideration and ultimate decision. It was a fun assignment, and in an indirect way, led to my new role at On Deck.

Teach For America's summer orientation and training has always been in-person. One of the questions a year ago was if and how we could make it virtual given the many layers of COVID restrictions. So, I was on the lookout for groups, teams, programs who were capitalizing on the shift from in-person to virtual. Everyone had moved to Zoom. Few were doing it well, especially in the middle of March.

On Deck was one of the places that made the transition, made it fast, achieved results, and generously shared what they learned. My first introduction to On Deck was via Twitter:

The summary was a goldmine for imagining all the different ways virtual didn't have to mean worse in terms of participant experience and learning and strength of the cohort community. I started following On Deck and watched as their flywheel caught and they moved with tremendous velocity to grow their impact.

My assignment from Elisa wrapped up successfully, TFA made the virtual leap for new teacher summer training, and we joined countless others navigating the day-to-day of a pandemic in schools, neighborhoods, and our families. It was all a whirlwind, and I'll be trying to make sense of it for the rest of my life.

Like many, I could also sense that the pandemic had the potential to change education in the U.S. in lasting ways. I wrote about this last May (and then graded myself afterward). Throughout the summer, I felt drawn to exploring how the future of education after the pandemic could look, and as importantly, how to get there while resisting the forces that were more likely to pull us back to a stagnate normal. As the school year started, I was a having a conversation with TFA's national leadership about my intent to transition after 14 years with TFA and 10 as the Executive Director of TFA-Connecticut. I knew then that I wanted to explore opportunities at the intersection of learning and internet. I also knew I would need time to position myself to meet and learn from numerous leaders much more proximate to the opportunities and challenges within space.

Enduring Points of View

I felt privileged to lead at TFA for so long because of the principles we held. Over time, several ideas have become important to me, and I saw them come to life during my conversations with On Deck as well.

1. Talent is broadly distributed across the country and around the world, but opportunity is not.
2. There is much more, and much greater, human potential than our current systems for cultivating it acknowledge, much less support.
3. Highly capable teams with diverse and complementary skills and perspectives can figure out just about anything so long as there is an ample stock of humility all around.  
4. Learning by doing is an accelerant to progress and is too often an underrated approach to growth.
5. The answer, more often than not, is leadership. People, including those in positions of authority, will often spend a lot of time trying to find a different answer.

On Deck is a start-up. While I clearly favor the bull case for the business, the bear case is real and frequently examined (see #3 above). I'm looking forward to the many relationships I'll be privileged to forge with my new colleagues just as I'm relishing the opportunity to be thrown into the deep end of a fast-growing and still-young endeavor.

With the transition also comes a fair amount of reflection and gratitude for my time with Teach For America. Working with so many incredible and dedicated colleagues, partners, and friends provided blessings and memories far beyond what I can count. It was a true honor to grow, to lead, and to contribute with Teach For America.

I'll be posting here with some regularity, and do invite you to follow along and stay in touch. Thank you!

p.s. For those of you who have joined me on a Zoom over the past year, you've probably seen the image at the top of the post. It's been my virtual background as I've worked from my basement storage closet (one of the realities of WFH with 5 kids thundering about!). I've grown quite fond of this tree. One day, I hope to find it. Or, better yet, plant one that grows to be like it.