Covers: 1) How Startup CEOs can manage and assess CTOs, and 2) Tactics for people becoming a first time CTO in a startup company.

1. A look into methods for the CTO Role interacting
with different parts of building a startup company.
Bryan Starbuck Bryan@WhiteHatEngineering.com
WhiteHat Engineering, Inc.
We are the engineering team for a Business founder
Startup CTO Role
CTOCEO
Department
Heads
Board of
Directors

2. TalentSpring Founder & CEO - Acquired in 2010
B2B Enterprise SaaS company with Artificial Intelligence / Machine Learning
SPARKON Founder & CEO - 2011 to 2013
B2C Online learning & Passion Discovery
Owner at WhiteHat Engineering: (Current)
Our engineering team builds startup companies & products
Bryan Starbuck
STARTUPS & ENGINEERING Bryan@TheStarbucks.com

3. I’m searching for:
Business Founder
with an idea
CTO
Technical Founder-type
Brings an engineering team
I look for Business founders.
I act as CTO. I also bring in
3 software engineers.
And we build out the
company aggressively

4. 4
This talk is for:
Anyone who wants to
transition into a
CTO
Any first time startup
CEO
for managing &
measuring their CTO
or

5. 5
Techniques in this talk
My techniques are just my
$0.02 opinions.
You will do things, your way.
I want to create a discussion at the end.

6. 6
This talk is about CTO exec skills
This talk is NOT about coding or
programming technology skills.
Those skills can be learned at
Udemy.com and elsewhere.
This is talk is about the CTO-specific skills.

7. 7
VP of Product Management
Early on, CTO often needs to back-fill “VP of Product”.
Later, a VP of Product Management can join.

8. 8
Startups built out with significant momentum
This is designed for startups with serious momentum.
Swift to market. Swift to grow in market.
Great for companies who raise capital.
NOT for companies bootstrapping and going slow.

9. 9
The CEO picks the GOAL of the company
CEO owns the VISION
and GOAL of the company
I’ve found the Pitch Deck is a great way to pin down
lower level details. Keep the CEO & CTO on the
same page, and others who follow.

10. Blue Prints
of the building

11. 11
CTO in blue print designing mode…
I found this process
IRONS OUT
startup plans, AND
unifies CEO & CTO. Engineering Sprint work items
SPECs
Product Road Map
Pitch Deck
(Top Strategy, Vision & Goal)

12. 12
Pitch Deck is great for top level planning
The pitch deck is great to unify
on the TOP level VISION.
And then pin down medium
level decisions.
Engineering Sprint work items
SPECs
Product Road Map
Pitch Deck
(Top Strategy, Vision & Goal)

13. 13
Product Roadmap & Milestones
Engineering Sprint work items
SPECs
Product Road Map &
Milestones
Pitch Deck
(Top Strategy, Vision & Goal)
The Product Roadmap is then
great to pencil out FEATUREs
until LAUNCH, and thru
milestones

14. 14
SPECs for Distributed teams, etc.
Engineering Sprint work items
SPECs
Product Road Map
Pitch Deck
(Top Strategy, Vision & Goal)
“Just in Time SPECs”
SPECs make plans STICK.
Great for Distributed teams.
Great to centralize information.
Don’t let everything blow in the wind.
Emails. Verbal discussions.

15. 15
SPRINTs for top execution
Engineering Sprint work items
SPECs
Product Road Map
Pitch Deck
(Top Strategy, Vision & Goal)
Sprints are great for measuring
execution SUCCESSES and
FAILURES.

16. Strategic
facets of building the
startup from the early days

17. 17
Q: Do we deliver on this
promise?
Q: Do we have a narrow focus?
Q: Are we building too much?
More than is needed for
customers to buy?
Brand Promise
It is great to build a startup
against a:
BRAND PROMISE

18. 18
Q: How do we position our
unique advantage?
Q: How is positioning wrt
changes in the market?
Q: Does our strategic positioning
mean customers will buy us
INSTEAD, even when we are
the same price?
Positioning Strategy
POSITIONING
STRATEGY
Do you have a strategy?

19. 19
Q: Required when raising capital
Q: Did we REALLY create an excel financial projects making sure we
can reach that large market size?
Actually reaching market size
Will pricing and market size allow
us to reach our goal?

20. Strategic use of
Time

21. 21
Down the rabbit hole
Engineers start off their career going down the rabbit hole,
… as they focus on technical build outs
SYMPTOMS: Bad estimates, missed deadlines, etc.

22. 22
Accountability to time
Measuring everything to TIME is critical:
a) Do we have enough resources to meet that
date?
b) Are we starting to fall behind?
c) Can we estimate correctly?
d) Do we spot problems, early when they build up?

23. 23
Two Sprints per Month
Two sprints per month is great
a) Easy to plan
b) Agile
c) Every dev self-manages to finish
d) Measuring success in board meetings

24. CTO Decisions
on building out a company

25. 25
Technical Co-founder CTO
As a technical co-founder, each area of the
strategy & pitch deck needs to be double checked
a) Dev team size & capital needed to reach milestones
b) Math in financial projects reach market size
c) Product   Brand Promise
d) Positioning Strategy

26. 26
UI Design summarizing busines
As a technical co-founder, each area of the
strategy & pitch deck needs to be double checked
Is it very simple? Verify CEO & CTO on the same page. Understandable at one glance?
An important factor:
One screen that summarizes the product (& brand promise).

27. 27
Verify product scope isn’t too broad
First time business founders can fall in love
with delivering a huge range of features.
Co-founder (technical) should verify a clear
narrow focus.

28. Operational Efficiency
for the engineering team
From founding until profitable.

29. 29
Every sprint highly productive?
Do you have the system to MEASURE high
vs low productivity? Every month?
Board of Directories will measure this
directly, or indirectly

30. 30
Agile != Unaccountable
Be careful: Some engineers want
AGILE == UNACCOUNTIBLE
A board of directors & CEO expect
managing engineers with accountability

31. 31
Board meetings: Measuring through-put
CTOs need to present their
DEPARTMENT at board meetings
SUCCESS vs POOR execution
should be measurable.
Needing to fix a problem is okay.
Not knowing you have a problem is NOT okay.

32. 32
Sheltering DEVs
Devs want to be sheltered, when they are
accountable to deliver on commitments.
Two week sprints is a great sheltered window.
Prevent external from engineering from causing CHURN. Prevent
CHURN  high moral & devs will remain accountable.

33. CEO   CTO

34. 34
CEO  CTO
CEO communicates the VISION, GOAL
and FOCUS of the company.

35. 35
Blue print view of the company
Walk thru each stage
Engineering Sprint work items
SPECs
Product Road Map
Pitch Deck
(Top Strategy, Vision & Goal)

36. 36
CEO  CTO sync up
Sync-up with fire hose like communication.
Blueprints get updated. CEO can focus on building up everything
external: Fund raising, partnerships, customer acquisition, branding,
hiring, etc.

37. CTO  
Board of directors

38. 38
Board meetings: Measuring through-put
CTOs need to present their
DEPARTMENT at board meetings
SUCCESS vs POOR execution
should be measurable.
Needing to fix a problem is okay.
Not knowing you have a problem is NOT okay.

39. 39
Sales teams & Product team
Sales teams can blame the product team.
Sales teams are under tremendous pressure on reaching quarterly
revenue targets.

40. CTO 
Department Heads

41. 41
Keeping everyone on the same page
Writing the PLAN-of-RECORD down
will help make it “stick” across a team.
Pitch deck. Projected financials. Product Roadmap.
Milestones. SPECs. Work items.

42. Other Topics

43. 43
Start to launch in 5 months
CTO + 3 full time devs.
Launch in 5 months
(after starting to code)
This is a good challenge
and planning discussion.

44. 44
After launch
Try for 3 features ONLY for launch.
Then nearly all development after that
goes towards customer acquisition.

45. 45
CTO Cutting months to growth
It is very easy for a startup to “Throw
away 3 months”, several times.
CTO’s job is to prevent this.

46. Open up discussion

47. An engineering team that builds
entire startup companies
from the ground up
WhiteHat Engineering
STARTUPS & ENGINEERING
Early Stage Crypto-Currency & more

48. THE END
Bryan@WhiteHatEngineering.com
@BryanStarbuck