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
2. What follows is a true story, from an individual’s perspective #sincewebeinhonest
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 > Perfect
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
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 changes
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 metrics
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 work”
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 crucial
67. CatskillsConf.com Oct 23-25, 2015
68. Aaron Quint @aq quirkey.com/hireme github.com/quirkey beatsryetypes.com catskillsconf.com THANKS!