Wolf of Williamsburg / The endeavors

Shutterstock

VP of Technology, New York / 2010–2015

I spent five years at Shutterstock as VP of Technology. I scaled infrastructure, core services, and data teams through the company’s $3B IPO, growing the team from 3 to over 80 engineers and owning a $10M+ infrastructure and operations budget.

Pre-AWS, we built a global network that held 99.99% uptime and stored over 1.5PB of data.

From the archive

  1. The Long Way HereI build technology companies, work with startups, run and ride bikes, fix old houses, and start more side projects than I need.
  2. Burying the Lead a BitI applied to Chicago Booth without an undergraduate degree while a Wahoo offer, a house purchase, and Apply all kept moving.
  3. Skip That Bachelor'sCornell encouraged me to apply for its Executive MBA Metro NY program even though I never finished college. I got excited before I got careful.
  4. Tell Me the Truth, LinkedInAfter years of building startup teams, I started asking what a much larger technology company might offer and what I would have to give up.
  5. Nine Out of TenA recruiter suggested I talk to a venture firm. I explained the unfinished degree, years inside startups, and why most firms might still say no.
  6. The Wrong Kind of UnicornThree recruiters pitched senior engineering roles at giant companies. I sent them the same answer: impact, ownership, and an interesting problem.
  7. Sixty People, Two Hundred ThousandAaptiv had reached about 60 people and 200,000 paying members. I was recruiting, reviewing Peloton, and logging searches that returned nothing.
  8. The Network Kept WorkingA recruiter from Reonomy, a product colleague from Peek, and friends from the Shutterstock years all resurfaced while I built the team around Aaptiv.
  9. I Needed a Peaceful NightAfter thinking nonstop about an offer from Aaptiv, I declined because I still wanted to build a company from the beginning.
  10. More Interesting Than ExpectedA short conversation with Vimeo left important questions untouched, but the company itself gave me a reason to keep talking.
  11. Too Much for One CallA conversation about my Shutterstock years made one thing clear: I still wanted the mess and momentum of building early.
  12. I Need a ManagerI had let the management system slip while Reonomy grew, and the number of direct relationships was no longer workable.

99 more in the archive.