Clear-eyed counsel and hands-on help for founders and their teams.

Air is the creative operations platform (think: Dropbox, but for creative and marketing teams). I joined in summer of 2020 as Head of Strategy and Growth and built out go to market, overseeing sales, customer success, and analytics.

During my tenure we doubled ARR, more than doubled the annual growth rate, and achieved first-year net ARR retention well over 200%.

I moved us to a freemium business model, overhauled pricing, established the analytics function, and focused the ideal customer profile.

Squarespace (NYSE:SQSP) is on the of the leading platforms for building a website and online business. I joined as an entry-level data analyst when it was fewer than 70 employees and less than $25M in revenue. I finished in February 2020 as the SVP of Strategy, the member of the executive team responsible for data science, business development, international expansion, and half the product organization. Over those eight years the company grew headcount >15x (to 1,100+), revenue >25x (to $500M+), and valuation >50x (to several billion). What a ride.

The teams I worked with accomplished a lot. The credit for these successes belongs with the many individuals and teams that drove results; my role was leader, coach, and, at times, final decision-maker.

Product

In mid 2017, established a new Growth function; by mid-2019 the team was delivering sustained, all-time company highs for new trial volume, visit-to-trial start rates, and premium plan mix.

In late 2017, led the rebundling of our core website plans; the impact was millions of dollars in 2018 and tens of millions of dollars over three years.

In late 2019, oversaw the launch of the biggest update to our core website builder in seven years; the release improved the trial-to-purchase conversion rate and drove millions of dollars of 2020 impact

Built Growth from zero to nine PMs, took over our CMS and domains business (another five PMs), and temporarily managed the rest of the product managers while another leader was on parental leave (another six PMs). The combined product, design, and engineering org was several hundred.

Strategy

Grew the analytics function from two BI analysts to over 20 deeply technical data scientists responsible for marketing attribution, A/B testing, retention modeling, product measurement, and more.

Oversaw teams focused on business development (3), international go-to-market strategy (3), and product localization (5).

Shepherded the launch of two new business lines, domains and G Suite, that now represent tens of millions of dollars of annual revenue.

Guided the initial launch and later growth of Squarespace Circle, our community for design professionals.

Marketing

On two different occasions, for seven months each, took on temporary leadership of the marketing team.

Managed about two dozen people and a media budget of over $100M.

Led media buying and strategy for two Super Bowl campaigns.

I was lucky enough to be at the heart of this as a policy analyst. I joined just as my team was getting access to the databases that contained decades of fine-grained case and court appearance data; our team used this access to build a variety of reports and tools for executive management and other data-driven initiatives. 

Designed and coded (with one other analyst and an IT developer) an internal gang-tracking system

Implemented geocoding infrastructure and began location-driven data analysis

Closely advised IT on a complete consolidation and redesign of all office data systems

My earlier jobs are a combination of stereotypical stops on the now-abandoned law school track (a year as a paralegal at a white collar law firm post-graduation) and more esoteric fare. I spent the summer of 2008 using grant money to study jury selection and trial behavior in Philadelphia. I contributed to legislative recommendations accompanying indictments for stealing body parts in the summer of 2007. For three months in 2006 I camped across Pennsylvania and New York in search of deer ticks as a field researcher for a CDC study on Lyme disease. (Here's how to catch a tick, though somehow I caught none.) The summer before that I interned at the Academy of Natural Sciences helping catch snakehead fish, which can live for days out of water thanks to a partially-developed lung system. (I caught plenty, thanks to an electrified wire we dragged through the water to shock the fish.)

I earned a BA, cum laude, in Psychology in 2009. I’m still happy with the major despite the fact that half the science has since been discredited. The widely variable quality promoted critically thinking skills, or at least that’s what I tell myself.

Most of my extracurricular energy went into the Yale Daily News, where I was a sports editor. In many respects it was the best-managed organization I’ve ever been a part of — imagine turning over the entire management team of a 100-person company every year without having the wheels fall off, and that’s the YDN. You can read how it influenced me here.