Slides from Dave Kellogg's presentation at SaaStr Annual 2019 in San Jose, entitled Five Questions CEOs Struggle With.

1. 5 Questions CEOs Struggle With
(and some thoughts on how to answer them)
Dave Kellogg
Former CEO, Host Analytics
Author, Kellblog (www.kellblog.com)
@kellblog

2. Who Is This Guy?
• 2x CEO with 10 years experience in $0 to $100M range
• Host Analytics, MarkLogic
• 2x CMO with 10 years experience in the $10M to $1B range
• Business Objects, Versant
• Independent board director
• Alation, Nuxeo, Granular (sold), Aster Data (sold)
• Early/mid-stage advisor and/or investor
• e.g., GainSight, Tableau, MongoDB, Floqast
• Started as first-line technical support rep at Ingres

3. 5 Questions CEOs Struggle With
1. When do I next raise money?
2. Do I have the right team?
3. How can I better manage the board?
4. Should I worry about competitors?
5. Are we focused enough?

4. 1. When Do I Next Raise Money?
Only-kind-of-glib answer
• When? Now.
• How much? As much as you can.
• From whom? The best VCs who’ll fund you.

5. Thoughts on Money-Raising
When?
• About 2-year cycles
• As long as you need to ensure the next round is an up-round
How much?
• Financial model and scenarios are critical
• To go 2 years, even in your downside scenario
Just because you raise it doesn’t mean you need to spend it
• Trigger spend on milestones, not timelines
Can you afford not to fight the arms race?
• King-maker world = the better the category the bigger the problem

6. 2. Do I Have The Right Team?
Lorden’s Law
• Does each individual bring or take energy?
Kellogg’s Law
• Do you look forward to meeting with them?
Machiavelli’s Principle
• Do they work well together?
• Warring Princes = Weak King
Delivery track record
• Are they delivering results or explanations?

7. Deeper Thoughts On The Right Team
How often do your direct reports really challenge you?
• Challenging vs. simply irritating direct reports
Do you have “sell-by dates” for people in current role?
• Without upgrading <x>, probably need to replace by <y>
Do you have a mix of veterans and up-and-comers?
• Are your really hiring people better than you?
What is the board’s perception?
• “Sarah brings on A players” vs. “Sarah hires people she feels
comfortable with.”

8. 3. How Can I Better Manage The Board?
Universal desire among directors to “add value”
• It’s easy to be pattern-matched to death
The more financial, the more they care about two things
• Executive team and numbers
Make board meetings a board meeting topic
• What do you want? Who does it best? Can I speak to them?
• Assume slides read or not-read before meeting?
• Inspect the e-staff at board meetings?
Coach the e-staff to have the right attitude
• Chance to shine vs. meeting to survive

9. Advanced Board Management
Get them working for you!
• Who knows an exec at our top 15 this-quarter prospects?
• Who went to GSB with board members at these accounts?
• Who has a company with an amazing metrics-driven CFO?
• Who wants to make a small committee with me focused on
<key concern topic>?
• Who wants to help me get executive comp done and
approved on time? (Comp Committee, reframed.)

10. 4. Should I Worry About Competitors?
Yes, they are trying to kill you
• “If you know the enemy and know yourself, you need not fear the
result of 100 battles.” – Sun Tzu, The Art of War
No, leaders must blaze their own trail
• “Never lead from a position of fear.” – Benioff-ish, Zen-ish
WARNING: PROVERB CONFLICT!!

11. Thoughts on Driven-ness
Vision-driven vs. competitor-driven vs. customer-driven
• Avoid this either/or mindset!
You need to
• Speak like you’re vision-driven
• Create a culture that’s customer-driven
• Make strategy and set goals like you’re competitor-driven (but
don’t talk about it too much)
Oracle refused to recognize Ingres as a competitor
• Yet stack of Ingres competitive docs was 3x deeper

12. 5. Are We Focused Enough? (Probably Not.)
“Phenomenal cosmic power! Itty, bitty living space.”
-- The Genie in Aladdin
“Phenomenal cosmic vision! Itty, bitty market focus.”
-- Geoffrey Moore on strategy (paraphrased)
Examples
• From Documentum to Amazon to Facebook
Strategy != vision
• Among other reasons, strategy is ordered

13. 6. Are We Winning? (Bonus Question!)
The “dead moose” question for you and your board
• If strategy is the plan to win, then what is winning?
Easily provokes a great board discussion
• Best done 1-1 then in the group session
So many different answers when people speak honestly
• Find out what they are!
Incredibly important factor in employee retention
• People want to work at a firm that’s winning

14. Conclusions
Everyone ponders these questions
• In a way they define the startup CEO job
Ponder them, too.
• With your board, advisors, industry watchers, mentors, …
“Management is doing things right, leadership is doing the
right things.” -- Peter Drucker

15. Citations and References
Social Capital: Interim 2018 Summer Letter
• Speaks to changes in venture capital, King-making and such. Superb.
Kellblog:
• Sales is from Mars and Engineering is from Venus
• Veterans vs. Up and Comers in Startups
• Challenging vs. Simply Difficult Direct Reports
• I Don’t Want to Talk to You Any More
• A Note to the CEO, Drive the Board of Directors
• The Question that CEOs Too Often Don’t Discuss with the Board
Geoffrey Moore: Inside the Tornado
• Do not pass “go” without reading this classic
Robert Burgelman: Strategy as Destiny
• Introduces the idea of strategy as “the plan to win”

16. Thank You