-My impression of our Product and Engineering orgs after 5 years here is that they are fairly conservative and slow-moving. We are behind the curve technically in many areas, and our roadmaps move really slowly. I don't know what the solution is, but lack of innovation on product and engineering are a serious long-term problem we face.
-We are a tiny player in our competitive space, and that's not changing much over time. That lack of rapid upward momentum in terms of our business is very different than in the early years here, and it's sometimes hard to stay motivated without big growth prospects in the future. My team is growing really slowly (if at all) and feels like treading water sometimes.
-I think we are moving too slowly in moving our HQ into San Francisco. For too long our physical location has been unduly influenced (in my opinion) by where our executive team has chosen to buy homes. Most employees are in SF or East Bay, not Marin, and there is a huge disconnect between the personal interests of execs who would like a short commute and the majority of the talent base who bears the cost of long commutes, lack of quality public transit, and unaffordable real estate for us to be in Marin. If we want to be a real company, we need to act like one and move to where the talent is -- not where our exec team wants to have a pleasant lifestyle (and can afford to live).
-Our data infrastructure is not great. This is a hard problem to solve, at least with current leadership on the relevant teams. But other tech companies have figured this out, and we could do better. Data is too slow, not well documented, not widely accessible, and hard for product managers and business decision makers to get access to.