richardFINEman
However, if the OP is speaking the truth about the timeframe he got shares from, he is guaranteed to be up. There are definitely people who lost money on this deal, but definitely not Series A people.
On the valuation. Optimizely's pre-exit valuation rose in every VC round since changing the focus of the business from SMB (Series B) to Mid-Market (Series C) to Enterprise (Series D). The valuation of the exit took a hit for reasons that were not the enterprise focus. I could say more here, but consciously choose not to.
The self-serve model at Optimizely was certainly flawed. If VWO was able to build it profitably, that's likely because their labor costs, being based in India, are substantially lower than Optimizely's. Keeping a legion of engineers funded in SF has very different unit economics than keeping engineers funded in India.
Now on your last argument, that self-serve customers could acquire enterprise accounts, I certainly agree. If that strategy were better executed, it could have created a valuable pipeline. But the self-serve to enterprise funnel was sorely lacking, and when self-serve was cancelled, the business benefited financially and migrated everyone to the new pricing model for substantial success.
Its easy to look at Optimizely's final fortunes and link that to the enterprise approach, and I won't argue they're completely unrelated, but there were very different factors that caused Optimizely to fold into EPi's acquisition spree.
One of the important distinctions between Optimizely and most developer-first platforms is that experimentation is a hard practice to pick up. Most companies have difficulties getting their programs off the ground and keeping them funded, let alone grow or scale them. Small digital businesses struggle more for several reasons: 1) they have few resources, so teams are understaffed and resources are pulled easily, 2) they have little money, so the percentage uplifts are rarely motivating, 3) they have little traffic, so it is harder to get a statistically significant measure in their experiments
Because of these issues, Optimizely always had really poor retention in the SMB space. Nonetheless, the SMB customers helped Optimizely build up a brand name, build up legions of practitioners, and get the skills and experience to go after the Enterprise market. When Optimizely started acquiring enterprise customers, retention improved substantially.
This isn't to say that there aren't lots of problems with Enterprise sales and that Optimizely didn't make tons of cultural mistakes in that pivot. But on the core financials, Enterprise kept Optimizely afloat. The problem wasn't the pivot to enterprise, but the trade-offs that were mismanaged along the way. The path to enterprise was inevitable and correct.