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The Good, The Bad, The Ugly of Growth

The Good, The Bad, The Ugly of Growth

In 5 years Paperless Post went from 5 to over 100 people and from a dev team of 2 to 40. I was there for the entire ride as the CTO and not only helped shape the technology but also the culture and structure of the team. We constantly were changing and developing new strategies to achieve our goals. We called this "Continuous Process Delivery", in which we were never satisfied by not only the end product, but the way we were getting there.

Through my time as CTO of Paperless I've seen first-hand the triumphs and tragedies of growth. We did some great things that let people improve as individuals and ship a massive amount of product. We were self-reflective the entire time and that let us see that what we made a bunch of mistakes a long the way as well.

I'd like to take you on a very honest journey of one teams story.

Aaron Quint

June 10, 2015

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  1. In 2015 • > 1M receivers every week • Revenue

    in the 10s of $M • > 110 Employees, > 40 Dev/Ops • Office across 2 floors in FiDi
  2. In 2009 • 0 Receivers Weekly • $0 Revenue •

    4 Full Time Employees, 1 Full time dev + a number of consultants (including myself) • Using a set of 4 free (windowless) cubicles in one of our investors offices (which happened to be a women’s lingerie co)
  3. Find people who could work in as many places as

    possible, and were OK with uncertainty We tried to grow cautiously
  4. I like to think that I helped Over 5 years

    I got to watch individuals grow
  5. Not my first rodeo, but I’m not a grizzled commando

    either We were all [relative] noobs
  6. We were open to criticism. We knew as a team

    that we were probably doing a lot of bad things
  7. But we were constantly aware of what wasn’t working. This

    is not to say that we did a great job implementing change
  8. You can be “open” but if your message isn't clear,

    it’s not going to help Transparency actually necessitates clarity
  9. Take it in stride? What happens when you set an

    arbitrary and potentially unrealistic goal and Fail?
  10. Life, babies, balance, etc. I stepped down for a many

    reasons that won’t fit into a single talk
  11. And all are working to address the bad and ugly

    Paperless Post is in amazing hands right now