Recent Essays
Essays on engineering leadership, value-based care, and the craft of building.
Why Value-Based Care is Harder Than Rocket Science
A 4-part series on why fixing American healthcare from the inside is harder than it looks.
An introduction to building software for value-based care
This post argues that building successful software for value-based care (VBC) requires a shift in mindset: create a Customer Relationship Management (CRM) tool, not just a better Electronic Health Record (EHR). VBC realigns healthcare incentives around long-term patient outcomes, succeeding through proactive, relationship-based care rather than transactional services. Technology's role is to support this relationship by helping care teams orchestrate interventions effectively. The most valuable tools are often simple and pragmatic, focusing on the unique, core needs of the care model and enabling proactive management of patient health.
Learnings from building Kelp: Getting people the information they need when they need it is hard!
Reflections on pausing the contextual recommendation tool, Kelp, concluding that its goal—getting people the right information at the right time—is nearly impossible for a third-party app to achieve. The core problem is technical: without deep, OS-level access to user data and behavioral signals, recommendations remain mediocre. True contextual help must be built into the operating system itself. The key business takeaway was the need to solve a highly specific, paying use case for a narrow audience before attempting a broad, cross-platform solution.
Learning from a Hyper-Growth Startup
This reflection on leadership in a hyper-growth startup argues that self-management is the most crucial skill. Management in such a chaotic environment is inherently reactive and emotionally draining, not strategic and proactive. The key to effectiveness is to abandon "ruinous empathy"—the futile attempt to please everyone—and instead fiercely conserve personal energy for high-impact moments. This is achieved by accepting failure and tradeoffs as constant, communicating them transparently, and focusing on maximizing success in key areas rather than fighting every fire.
Is Buying in Brooklyn Worth It?
Brooklyn homeownership is not "worth it" as a financial investment. After accounting for renovation costs, high transaction fees, and the opportunity cost of not investing in the stock market, my profitable-on-paper sale was actually a financial loss. The true costs were the non-financial headaches: months of living in construction dust, battling city bureaucracy over permits, and fixing bank errors over property liens. I conclude that you buy a home not for the return, but for the control and satisfaction of making a space your own.
Recent Photos
The system reveals itself when you lean in.
About Me
I am consulting while working on Kelp, an AI assistant that helps executives stay on top of their increasingly vast scopes. I'm drawn to product problems where the hard part is messy data, complex requirements, and challenging customers.
Here's a little bit more about me:
I came into tech through art — a fine art high school at UNCSA, BFA from the Museum School in Boston, then a couple of years as a visiting researcher at the MIT Media Lab and MIT CSAIL publishing in human-computer interaction, then leading at Artsy where I ran our public facing website, live auctions and art fairs teams. Most recently, I spent nine years in healthcare: joined Cityblock Health as the first engineer and grew with it — eventually running the engineering org as we hit a $1.3B valuation with fewer than 25 engineers (pre-AI) — and over three years as CTO of Firsthand, including holding the technology org together through growth to ~28 offices and then significant a wind-down. Having now seen a full startup cycle, I'm more optimistic than ever at the power of small empowered teams to tackle the hard problems we face.
Outside of work, I'm in Park Slope with my partner, spending more time building apps to teach me Chinese than studying, and writing here about how I got all my gray hairs， engineering leadership, and why VBC might just be too hard a problem to solve.
Selected Work
Firsthand
Led the technology organization across Product, Software, Data, IT, and Security, scaling the team from 3 to 25 while supporting rapid physical expansion across 28 offices. Architected helpinghand, our proprietary AI-powered care management tool, and secured HITRUST r2 certification under strict deadlines.
Kelp
Founded Kelp to filter our ocean of information down to just what you need right now. Built a Chrome Extension with integrations across major workplace platforms. Now it is an AI assistant focused on helping executives stay current on industry, technology, and cultural shifts.
Cityblock Health
As the 3rd team member, I was instrumental in incubating and launching Cityblock from within Alphabet's Sidewalk Labs. My team built the core data and software technology foundation, including data-sharing partnerships with payers and Commons—the proprietary care management platform.
More on LinkedIn
Many past projects such as leading Artsy.net's public web presence and auctions, Motivate (Citi Bike), HCI research at MIT CSAIL and working at the MIT Media lab on visualizations for Ars Electronica.
HCI Publications
Assisted Self Reflection
Moore, Van Kleek, Karger, schraefel — CHI 2010
Atomate It!
Van Kleek, Moore, Karger, André, Schraefel — WWW 2010