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.

Transcript

1. The Good, The Bad, and
   The Ugly of Growth
   Aaron Quint / @aq / QCon NY 2015
   

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2. What follows is a true story, from an
   individual’s perspective
   #sincewebeinhonest
   

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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
   

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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)
   

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8. 3 Full-Time Devs,
   0 Ops,
   11 total Employees
   I became CTO
   March 2010
   

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9. Good begets Great
   Bad begets Ugly
   

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10. So many features, so little time
    In the beginning it was
    all about :shipping:
    

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11. Good Thing #1:
    Creeds
    

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

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

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14. Roadies > Rock stars
    Helping > Winning
    

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

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

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17. The only best practice is that best practices
    change
    Understandable Working Code ==
    Best Practice
    

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18. agile deployment, focus on end-users
    #=> getting things done and
    constantly improving
    

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

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20. Find people who could work in as many places
    as possible, and were OK with uncertainty
    We tried to grow cautiously
    

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21. Good Thing #2:
    Interns!
    

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

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

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25. Good Thing #3:
    Mentorship
    

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26. I like to think that I helped
    Over 5 years I got to
    watch individuals grow
    

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27. Good devs know they can always improve
    Individual growth is key
    to group growth
    

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28. Not my first rodeo, but I’m not a grizzled
    commando either
    We were all [relative] noobs
    

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29. We were open to criticism.
    We knew as a team that we were
    probably doing a lot of bad things
    

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30. Good Thing #4:
    Self-awareness
    

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

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32. Not afraid to make changes to make our
    process better
    Continuous Process
    Delivery
    

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33. But we were constantly aware of
    what wasn’t working.
    This is not to say that we did a
    great job implementing change
    

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34. Great Thing #1:
    Mentorship as a Tree
    

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

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36. Great Thing #2:
    Open Feedback Loop
    

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

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38. Great Thing #3:
    Big Shippin’
    

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

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40. What is really?
    Not all rosy
    

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

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

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43. Also dangerous, people get hurt
    More People =
    More intentions =
    Harder to shift focus
    

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44. From written reviews/1-1s
    Collecting feedback
    into themes
    

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

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46. Bad Thing #2:
    Misunderstanding
    Transparency
    

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

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48. Which garnered respect, but not necessarily
    motivation/better work
    My understanding/method was
    to try to be open and upfront
    

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49. You can be “open” but if your message isn't
    clear, it’s not going to help
    Transparency actually
    necessitates clarity
    

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50. Transparency is about
    intention not action
    

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

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

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53. Take it in stride?
    What happens when you set an
    arbitrary and potentially unrealistic
    goal and Fail?
    

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54. The list keeps growing!
    Maybe you feel like you
    didn't get enough done
    

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55. Bad Thing #4:
    Hiring under duress
    

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

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57. Ugly Thing #1:
    Bad, Destructive Hires
    

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58. It means the wrong people
    for the wrong situation.
    That doesn't even mean
    bad developers
    

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59. Huge expense of time and energy
    Desperate to
    “Make it work”
    

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60. Ugly Thing #2:
    Burnout
    

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61. This brings us to my story
    

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

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63. Life, babies, balance, etc.
    I stepped down for a many reasons
    that won’t fit into a single talk
    

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64. And all are working to address
    the bad and ugly
    Paperless Post is in
    amazing hands right now
    

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65. Please do so!
    Learning and sharing what
    you’ve learned is crucial
    

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67. CatskillsConf.com Oct 23-25, 2015
    

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

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