Michael Wolfe outlines a "Startup Operating System" to help companies run effectively. The system focuses on cadence, planning, transparency, and three big ideas. Cadence establishes regular rhythms for meetings, reviews, and communications to keep the team synced. Planning involves setting goals and adjusting plans based on learning. Transparency means sharing all useful business information openly. The operating system aims to have a wildly talented team working hard on the right things through deliberate habits and practices.

1. The Startup
Operating System
Michael Wolfe
Advisor, Point Nine
michael@pointninecap.com

3. “You need to
execute harder!”

4. Founder or first employee at
five B2B companies
Two acquisitions, one IPO,
one in progress
Exec at two public
companies
VP Engineering, VP Product
Management, CTO, CEO
Advisor, Point Nine
About Me

5. There is no one way to do things.
But good companies tend to do
certain things well.
Keep it simple - this is not the
best place to innovate.

6. When you’re
starting up
Work like crazy
Try lots of stuff
Don’t kill each other
Hope and pray

7. Team ∙ Customers
Money ∙ Investors
Mo’ problems

8. Wildly talented people
Who get along
Working hard
On the right things
Adjusting as they learn
What you
want

9. That is not the
natural human
condition.
You have to be
deliberate.

10. The Startup
Operating System
The system of habits, practices, and
values you use to run your company

11. 90 people
Direct sales
Two offices
Enterprise

12. Cadence
Plan
Transparency
Three ideas

13. Cadence
The regular rhythm
(weekly, monthly,
quarterly)
of events that
happen at your
company.

14. Confidential 14

15. Sample weekly cadence
Exec team
meeting
Team
meetings
One-on-ones
Weekly
release
Forecast
callCustomer
readout
Mon
Tue
Wed
ThuFri
Company
meeting
Product
leads mtg

16. Board
meeting
Planning
offsite
Training / team
building offsite
Board
call
Replan
Monthly GTM
training
Monthly
GTM
training
Sample quarterly cadence
1
2
3
NPS
Surveys

17. Train the crap out of people.
Then train then some more.
Then do it again.
So bake it into your OS.
Why Cadence: Training

18. Syncs up the team.
Makes room for travel.
Reduces schedule conflicts.
Allows “meeting free” days.
Why Cadence: Logistics

19. People get to lead.
People know their window for
input.
Predicable schedules.
Why Cadence: Morale

20. Forces decisions to happen.
Encourages accountability.
Why Cadence: Speed

21. Adjust your plan based on new
information constantly.
We make changes every week.
Why Cadence: Agility

22. Focus
meetings on
decisions
and actions

23. 1-1’s are your #1 management tool
Find out what is happening at your company.
Ask about career direction and interest.
Test out ideas.
Do them with peers and skip levels, too.

24. Sample Company Meeting Agenda

25. The “Operating System” isn’t
just these individual events.
It’s how they all work together.

26. Exec
meeting
Team
meetings
Company
meeting
One on
ones
Decisions
Guidance
Priorities
Assignments
Decisions
Issues
Feedback
Reactions
Coaching
26
Connect
Motivate
Inform

27. Cadence
Plan
Transparency
Three Big Ideas

28. OKRs? V2MOMs?
GSOs? MBOs?

29. Keep it simple
Focus on a small number of goals
Cross-departmental goals

30. Example Plan

31. Board
meeting
Present plan
to company
Company
replan
Quarterly Planning Cadence
Mid-quarter
tweaks
Run the
company on
the new plan

32. Using the plan
Exec team
meeting
Team
meetings
One-on-ones
Weekly
release
Forecast
call
Customer
readout
Mon
Tue
Wed
ThuFri
Company
meeting

33. Cadence
Plan
Transparency
Three Big Ideas

34. Transparency
Everyone at the
company should
share all useful
information about
your business with
each other.

35. Confidential 35

36. Why Transparency
Team - good people want to be treated like adults
Learning - people want to learn and need the info
Motivation - people want to know their work matters
Relationships - people trust and get along better
Decisions - good information == good decisions
Velocity - people can execute without execs

37. Cadence and Transparency
Exec team
meeting
Team
meetings
One-on-ones
Weekly
release
Forecast
call
Customer
readout
Mon
Tue
Wed
ThuFri
Company
meeting

38. All data and
communications
are public

39. Bake transparency into the culture
Lead by example: ask lots of questions and share
lots of info.
Expect everyone to do the same, especially
managers.
Be on the lookout for people who are keeping
information private and give feedback.

40. Planning to
make sure you
are working on
the right things
Transparency to
keep people
informed,
productive and
motivated
Cadence to
keep people in
sync, making
decisions, and
executing

41. ✓ Wildly talented people
✓ Who get along
✓ Working hard
✓ On the right things
✓ Adjusting as they learn

42. Your employment cycle
Your product cycle
Your deal cycle
Your customer cycle
Other things we could have talked about

43. Keep tuning and tweaking it
It changes as you grow
Don’t stop when it gets tough
Final thoughts

44. Thanks
Michael Wolfe
Advisor, Point Nine
michael@pointninecap.com