Kimber Lockhart - CTO / One Medical at SaaStr Annual 2018 Big mistakes, little mistakes, costly mistakes, and strategic mistakes. This session will explore mistakes I made and those I narrowly avoided during my time scaling enterprise subscription products and services at Box and One Medical. We'll explore classic challenges like how to decide to build customer-specific functionality, how to let customers opt-out of changes and when to create process around interactions between sales and engineering teams.

1. Classic SaaS Product and
Engineering Mistakes
Mistakes I made and narrowly avoiding during my time scaling enterprise
subscription products at Box and One Medical
PRESENTED BY: KIMBER
LOCKHART
@Kimber_Lockha
rt

2. “So many roads. So many detours.
So many choices. So many
mistakes.”
- Sarah Jessica Parker

3. 01 02
03 04
Mistakes that add
exponential complexity
Mistakes in team
collaboration
Mistakes of misplaced
product strategy
Mistakes that doom your
tech stack
Four types of mistakes:
3

4. Mistakes that add
exponential complexity

5. 5
Exponential
Linear

6. 180 Combinations
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7. Exponential Complexity
Mistake #1:
Building a feature for your biggest deal

8. 8
Your Customers
Time

9. 9

10. 10
You’re
confident the
feature is part
of your future
core offering
It’s isolated,
but obvious.
It’ll be difficult
to break or
miss later.
You’re building
it for a handful
of customers
Many
customers are
asking for it
Implementing
as a setting,
not a hard fork
Feature is
hidden, it’ll be
easy to miss
or break later
Implications of
feature
interact with all
other parts of
the product
Work is
performed on
spec before a
deal is signed
More
likely a
mistake
Less
likely a
mistake

11. Exponential Complexity
Mistake #2:
Enabling change-adverse customers

12. 12

13. Exponential Complexity
Mistake #3:
Whitelabeling or going on-premesis

14. 14

15. Mistakes of misplaced
product strategy

16. Product Strategy Mistake
#1:
Dogfooding Inappropriately

17. 17

18. Product Strategy Mistake
#2:
Supporting unsupported workarounds

19. 19

20. Mistakes of team
collaboration

21. Team Collaboration Mistake
#1:
Product and engineering uninvolved in sales

22. Team Collaboration Mistake
#2:
Sales overinvolved in product and engineering

23. 23

24. Mistakes that doom your
tech stack

25. Tech Stack Mistake #1:
Scale and performance: too early or too late

27. 27

28. Tech Stack Mistake #2:
Casually agreeing to SLAs and pass-throughs

29. You
Your
Vendor
Your
Vendor
Your
Vendor
Your
Vendor
Their
Vendor
s

30. Tech Stack Mistake #3:
Accumulating or ignoring tech debt

31. 31

32. 32

33. “I make mistakes growing up. I'm
not perfect; I'm not a robot.”
- Justin Bieber

34. “I’ve been imitated so well, I’ve
heard people copy my mistakes.”
- Jimi Hendrix

35. “Making mistakes is a lot better
than not doing anything.”
- Billie Joe Armstrong