A Hypothesis: “Support Groups” for Enterprise CEOs
At our recent NYC Enterprise CEO Summit, I moderated a panel with Daniel Chait, CEO of Greenhouse and David Politis, CEO of BetterCloud (see here for a complete recap of the Summit and videos of the panels).
We only scraped the surface of a terrific discussion — the hard thing about hard things, the things you learn only after you have experienced it firsthand as a CEO. We talked about culture, hiring, managing, and evolving company processes and structure as your company grows.
But as with all great discussions, we ran out of time. We know that one of the most valuable things for a CEO is learning from fellow CEOs of enterprise companies a year or two ahead of them in scale: on things they wish they had known earlier, what processes would they have introduced, what did they do too late. We want these rich conversations to continue, beyond our annual Summit.
As such, we’ll be kicking off a series of closed-door, curated, 10-person Enterprise CEO “Support Group” dinners. Small and confidential — we want these discussions to be as honest and hard-hitting as possible, on the hard things you won’t hear anywhere else, and with a deep focus on actionable tactics (see a few questions below).
Does the term “Support Group” have a negative connotation? Maybe. But as one CEO told us: any CEO of any startup, early-stage, fast-growing company who pretends like they don’t need a support group would be lying. Come join incredible enterprise founders from all stages in New York City to learn from one another and openly share the mutual challenges you face.
If you would like to join one of our Enterprise CEO Support Group Dinners, please sign up here.
Top of Mind Questions for Enterprise CEOs: Culture, Hiring, Growth, and more.
- For CEOs who have run previous companies — what has been the biggest difference in company culture this time around, and your biggest lesson learned from your previous companies?
- Thinking back, what were the inflection points — 10, 20, 50, 100 — in terms of company size, when you had to make intentional process changes to culture?
- What is your employee feedback process? Do you survey your employees for employee experience? At what point did you start doing that?
- For those of you with distributed teams: at what team # did you start a second office? What has been the #1 tactic that has been most helpful in maintaining a cohesive culture for your company?
- As you grow, how do you ensure communications across teams doesn’t break down? (i.e. user manuals).
- Any tips to bridge the gap between sales/CS and engineering teams?
- Any tips to integrate senior hires into a founder heavy culture?
- What should you outsource? What should you never outsource?
- How do you correspond promotions (job titles) or salary raises, to performance reviews and rankings?
- What has been biggest learning (and subsequent action/change) from firing retrospectives?
- What happens when you have an amazing team player…but they can no longer get the job done? How long do you give them time to get coached, trained, leveled up?
- Do you think you effectively weed out poor performers?
- When do you hire an HR person? When do you hire a VP of Sales?
- When you set a big audacious goal with your team and you miss it, how do you address it?
- What do you do when your best employee asks you for more money when you are up all night trying to figure out what you can do to reduce burn?
- How do you handle an employee who is crushing all metrics but is poison for culture?
- As your company evolves — how do you level up your team for the skills they need?
- What has been most effective in developing and growing your teams? Do you pay for training, coaching, etc?
- Your first 3 sales hires sit in a windowless room with you, and heard your sales pitches directly. How do you ensure your training remains as high-caliber and high-quality as you grow and scale?
- How do you continue leveling yourselves up, as CEOs?
