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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. The Good, The Bad, and The Ugly of Growth Aaron

    Quint / @aq / QCon NY 2015
  2. What follows is a true story, from an individual’s perspective

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

    in the 10s of $M • > 110 Employees, > 40 Dev/Ops • Office across 2 floors in FiDi
  7. 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)
  8. 3 Full-Time Devs, 0 Ops, 11 total Employees I became

    CTO March 2010
  9. Good begets Great Bad begets Ugly

  10. So many features, so little time In the beginning it

    was all about :shipping:
  11. Good Thing #1: Creeds

  12. Started as an oral tradition, turned into a written guide

  13. We all live with the choices we all make Fixing

    > Complaining
  14. Roadies > Rock stars Helping > Winning

  15. Push for a balance of quality and quantity Working >

  16. Win in pieces, not all at once Small changes >

    Big refactors
  17. The only best practice is that best practices change Understandable

    Working Code == Best Practice
  18. agile deployment, focus on end-users #=> getting things done and

    constantly improving
  19. But very necessary Hiring was a painful and stressful process

  20. Find people who could work in as many places as

    possible, and were OK with uncertainty We tried to grow cautiously
  21. Good Thing #2: Interns!

  22. Ah, the boundless ambition and energy of youth!

  23. Started with 2 Dev Interns Grew to ~10 each summer

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  25. Good Thing #3: Mentorship

  26. I like to think that I helped Over 5 years

    I got to watch individuals grow
  27. Good devs know they can always improve Individual growth is

    key to group growth
  28. Not my first rodeo, but I’m not a grizzled commando

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

    that we were probably doing a lot of bad things
  30. Good Thing #4: Self-awareness

  31. Sourced from peers, managers, team Biannual Performance Reviews

  32. Not afraid to make changes to make our process better

    Continuous Process Delivery
  33. But we were constantly aware of what wasn’t working. This

    is not to say that we did a great job implementing change
  34. Great Thing #1: Mentorship as a Tree

  35. 3rd and now 4th Generation Mentors Each one Teach one

  36. Great Thing #2: Open Feedback Loop

  37. Meaningful feedback -> Meaningful Progress Changes came from reviews and

    turned into action
  38. Great Thing #3: Big Shippin’

  39. Create Tool, PAPER, iOS Apps Countless impactful features that improved

    our bottom line
  40. What is really? Not all rosy

  41. And making changes sometimes means redirection Moving fast means making

  42. Bad Thing #1: Top-Down Track Correction

  43. Also dangerous, people get hurt More People = More intentions

    = Harder to shift focus
  44. From written reviews/1-1s Collecting feedback into themes

  45. (or lack there of) A theme emerges: Transparency

  46. Bad Thing #2: Misunderstanding Transparency

  47. Who needs to know what? MGMT team was initially hesitant

  48. Which garnered respect, but not necessarily motivation/better work My understanding/method

    was to try to be open and upfront
  49. You can be “open” but if your message isn't clear,

    it’s not going to help Transparency actually necessitates clarity
  50. Transparency is about intention not action

  51. Goals are good But we tried to set goals through

  52. Bad Thing #3: Metrics in the wrong direction

  53. Take it in stride? What happens when you set an

    arbitrary and potentially unrealistic goal and Fail?
  54. The list keeps growing! Maybe you feel like you didn't

    get enough done
  55. Bad Thing #4: Hiring under duress

  56. Do they? Define desperate Desperate times need Desperate measures

  57. Ugly Thing #1: Bad, Destructive Hires

  58. It means the wrong people for the wrong situation. That

    doesn't even mean bad developers
  59. Huge expense of time and energy Desperate to “Make it

  60. Ugly Thing #2: Burnout

  61. This brings us to my story

  62. There’s a new CTO I’m now Chief Scientist

  63. Life, babies, balance, etc. I stepped down for a many

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

    Paperless Post is in amazing hands right now
  65. Please do so! Learning and sharing what you’ve learned is

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  67. CatskillsConf.com Oct 23-25, 2015

  68. Aaron Quint @aq quirkey.com/hireme github.com/quirkey beatsryetypes.com catskillsconf.com THANKS!