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Dave Kellogg at SaaStr Annual 2019: Five Questions CEOs Struggle With

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

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Dave Kellogg at SaaStr Annual 2019: Five Questions CEOs Struggle With

  1. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 16. Thank You