What is the job of a CTO and how does it change as a startup grows in size and scale? As a CTO, where should you spend your focus? As an engineer aspiring to be a CTO, what skills should you pursue? In this inspiring and personal talk, I describe my journey from early Red Hat engineer to CTO at Bloomon. I will share my view on what it means to be a CTO, and ultimately answer the question: Should the CTO be coding?

1. Should The CTO Be
Coding?
Joshua Hoffman (Independent)
Amsterdam | April 2-3, 2019

2. Set the radio to
channel 1!

4. Who am I?

5. Experience Highlights
• Red Hat
• Tumblr
• SoundCloud
• LeaseWeb

6. Who is this talk for?

7. This Talk Is For
• Engineers thinking about a career change to management
• New Startup CTOs (especially with rapidly growing teams)
• Anyone who wonders what a startup CTO does

8. Should the CTO
be coding?

9. What is a CTO?

10. “Executive-level position focusing on scientific and
technological issues.”

11. “The CTO develops policies and procedures and uses
technology to enhance products and services.”

12. “The CTO examines the short and long term needs of
an organization, and utilizes capital to make
investments designed to help the organization reach
its objectives.”

13. What is a
Startup CTO?

14. “Nobody really knows.”

15. “It’s a fuzzy sort of role that doesn’t really fit in a box.”

16. “It totally depends on the startup.”

17. Some Types of Startup CTO
• A Technical Founder
• Solo Engineer
• Lead Engineer of a small team
• Head of Product Team
• Head of Engineering Team

18. It totally depends on
the startup.

19. The CTO Spectrum
Startup———————ScaleUp—————————BigCorp

20. The CTO Spectrum
Startup———————ScaleUp—————————BigCorp
1-4 15-30 50-100 500+

21. The CTO Spectrum
Startup———————ScaleUp—————————BigCorp
1-4 15-30 50-100 500+

22. How did I get here?

23. Why be a Technology
Leader?

24. “Taking the lobotomy”
Photo by https://commons.wikimedia.org/wiki/User:Bz3rk
Creative Commons Attribution-Share Alike 3.0 Unported

25. Management
Chooses You

26. My First Management Experience
Photo by https://commons.wikimedia.org/wiki/User:Bidgee
Creative Commons Attribution-Share Alike 2.5 Australia

27. Management
vs
Leadership

28. What does a
Startup CTO do?

29. Stuff a Startup CTO
Typically Does
• Recruiting
• Coaching and Mentoring
• Help define Career Paths
• Help define Team Structure
• Influence Engineering Culture
• Maintain a Vision of The Future
• Coding?

30. My Top Startup CTO
Priorities
• Deliver top quality products and/or services
• Be a great place to be an engineer

31. Recruiting

32. –Amsterdam Economic Board Report: Fighting The Odds
“Developer and data scientist vacancies are
constantly open and it usually takes… more than 12
weeks to fill these vacancies.”

33. –Amsterdam Economic Board Report: Fighting The Odds
“The demand for Junior IT talents has doubled in the
past year, reaching 1 candidate per 26 vacancies,
with developers still being the most sought-after
candidates…”

34. Positive Candidate
Experience

35. Integrity

36. 5 Open Interview
Questions

37. “What advice would you give someone who is
considering a career change to software
engineering?”

38. “What is one book every software engineer should
read and why?”

39. “What advice would you have for a junior engineer on
their first day of work?”

40. “In your opinion, what is the difference between a
Junior and Senior software engineer?”

41. “What would you like to learn from us and what can
you teach us?”

42. Coaching and
Mentoring

43. Coaching
Advice or assistance that is immediately actionable.

44. Coaching
• Immediate feedback
• No relationship required
• Practical
• Incremental focus

45. Mentoring
A trusting relationship, built over time, typically in which a
more experienced person advises a less experienced person.

46. Mentoring
• Thoughtful advice
• A long term relationship
• More questions than answers
• Long term focus

47. Career Growth

48. Engineering Career
Levels

49. Engineer Level 1
• Influence: self
• Communicates clearly and effectively
• Actively involved in learning new skills
• Asks for help when stuck

50. Engineer Level 2
• Influence: team
• Regularly facilitates team communication
• Actively involved in learning and sharing new skills
• Helps others when asked
• Can solve small problems independently

51. Engineer Level 6
• Influence: industry
• Regularly writes research papers and/or conference talks
• Actively involved in coaching and/or mentoring other team
members
• Contributes to engineer onboarding program
• Can lead a large project involving multiple teams

52. Performance
Management

53. Leadership Example
How to change the behavior of 100+ engineers

54. Uptime 96%
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Creative Commons Attribution-ShareAlike 2.0 Generic

55. Outages occur primarily
during working hours

56. Outages mostly effect
new/active projects

57. MTTR
>180 minutes

58. –John Alspaw
“All outages are the result of someone doing their job.”

59. 7 Requirements
To Complete Any Task

60. Awareness

61. Tools

62. Skills / Knowledge

63. Capacity

64. Standard

65. Definition of Done

66. Measurement

67. Motivation

68. 7 Requirements
To Complete Any Task
1. Awareness
2. Tools
3. Skills / Knowledge
4. Capacity
5. Standard / Definition of Done
6. Measurement
7. Motivation

69. Solution:
Uptime Academy

70. Prepare a service for
production

71. Respond to an
incident

72. Conduct a post
mortem investigation

73. Uptime 99.9%
Photo by https://www.flickr.com/photos/dirrksv
Creative Commons Attribution-ShareAlike 2.0 Generic

74. Uptime Academy
1. Prepare a service for production
2. Respond to an incident
3. Conduct a post mortem investigation

75. Team Structure

76. Team interdependency is
a direct result of
architectural choices

77. Tech Debt

78. Engineering Culture

79. Way of Working

80. Vision of The Future

81. Should the CTO
be coding?

82. The CTO should
SOMETIMES be coding.

84. –Lisa Cash Hanson
“Leadership is the ability to guide others without
force into a direction or decision that leaves them still
feeling empowered and accomplished.”

86. Seven Secrets
Of The Successful Startup CTO

87. Never Stop Learning

88. Never Stop Teaching

89. Tech Over Taste

90. Elevate Others

91. Make Decisions

92. Plan For Tech Debt

93. Build and Maintain
Your Network

94. Seven Secrets of The
Successful Startup CTO
1. Never Stop Learning
2. Never Stop Teaching
3. Tech Over Taste
4. Elevate Others
5. Make Decisions
6. Plan For Tech Debt
7. Build and Maintain Your Network