(In no particular order.)
I should have hired a controller earlier–well before any other finance executives.
I spent too much time trying to also do operations. I should have doubled down on being externally-facing and brought someone experienced to be a COO... and by ops here I mean literally being a CEO but on the inside.
I approved refactoring (rewriting original code) at the wrong time. Instead, I should have pushed the product and engineering organization to develop new products to grow even faster than the 30% we were doing YoY.
I should have realized much sooner the Board provides opinions not directives. “Thank you for sharing your perspectives. We will discuss as a team and get back to you" instead of constantly overcommitting without too much thought.
I should have used more executive search firms to find senior leaders for more roles sooner.
I should have been more open to remote employees to expand our talent pool.
I should have used cash-on-hand more aggressively. (We had 50% of what we raised in our Series B on the Balance Sheet when we sold to Cvent for $100M.)
I should have put a monetary value on all perks and benefits we offered employees, including the value of the options we granted, to communicate true total compensation to employees.
I should have communicated my intentions more often so that it was never assumed I came from an unloving place. (I’m actively working on this: see my CEO 2.0 post).
I shouldn’t have succumbed to board pressure as it relates to goals. A CEO's intuition is right: underpromise and overdeliver. The Board's intuition is right, too: push for more. The answer is finding a reasonable middle ground and not succumbing to pressure.
Instead of getting defensive, I should have asked more questions.. this essentially achieves the same level of pushback without collateral damage.
I should have not shied away from using my intuition, which was often right, as a legitimate reason for doing things.