That's a great point and we totally missed our roadmap in 2013, by about 9-12 months. This is something that Zach Holman at Github addresses in why Github doesn't really communicate about their roadmap:
https://github.com/holman/feedback/issues/534
In our case it was because we were basing all of our roadmap on how we operated in 2012 when we were a much smaller company, think 5 people, servicing a much smaller customer base, say 500 customers.
It was early 2013 that our growth really started and we tried to remain optimistic about our ability to launch features. This turned out to be completely unrealistic. We had to scale our customer support department which at that time was basically myself and Etel who is our community director from 0 full-time people to 17 today. Our engineering team was all cofounders which we have since scaled to 10, and we had no SRE team which we've since also built out and recently hired Mark Imbriaco from Github as our VP of Ops.
Our tremendous growth was very exciting but it stressed every single area of the business. We had to raise two rounds in 2013. Though we closed our Series A in 2014 we actually began that process in early November of 2013.
As the customer base grew and began we also started to encounter more scale issues which began to shift our engineering focus away from feature and product development to bug fixes, refactoring, and re-engineering.
We would have wished that we could move faster and pay down technical debt so that we could move into developing features sooner but given our tremendous growth last year of scaling from 500-1,000 customers at the start of the year to close to 100,000 by the end of the year it simply wasn't possible.
Along the way we completely broke a few promises about when we would release new updates and features. Now we are finally at the point that we feel confident that we are able to develop and roll out new features and we have begun doing so.
We've certainly learned some valuable lessons along the way such as being very careful about the public promises that we make. It's hard to say at the moment, but I don't think that we will follow Github's model of being secretive with our roadmap, but we will certainly be more cautious with our estimates given how we have seen so many different factors play into our ability to release features.
I think any startup that has scaled has gone through similar problems and so it's a story which I'm sure has been repeated many times in history. We could have done a better job of staying ahead of these changes and more pro-actively communicating that we would be falling behind our product roadmap as a result and that's a personal failure on my end as I lead product in the organization.
Much like a startup evolves, matures, and changes overtime, I too have had to go through a similar process of learning and re-learning my role both as a cofounder and also as a product lead.
It's been very dynamic and interesting and certainly has been a tremendous growing experience and I've finally been catching up with the rest of my work now that we've settled so many different problem areas in just scaling a company and a business.
One of the first things was to get back on top of UserVoice and begin to provide more updates and visibility into the things that we've been working on and what's coming up. For other items we are still in the process of hashing out the details and providing better estimates so in those cases we are holding off before we make another public statement so that we can ensure we set the correct expectations.
Believe me that there is nothing more troubling to us as a company than letting down our customers, it is never our intention, and it is never out of ill-will, often times it happens out of being too optimistic. Like any trait there is a negative and positive aspect to it. As a cofounder you need that boundless optimism because there will be hard times. We had hard times when we spent 18 months with zero to little traction, and I'm sure we'll need that optimism in the future as well when we hit hard times or when the landscape shifts. During these periods it is essential. However, like anything else in life there is a balance. And, as essential as this optimism is to a startup it can also lead to issues such as these. In cases like that its a matter of being open and honest and saying yes we messed up, here is why, and here is how we are thinking about this problem in the future.
Hopefully that sheds some clarity on this area, especially since I was the one who was personally responsible for this in our company.
Thanks,
Moisey
Cofounder DigitalOcean