Ajay Vashee — who spent the last eight years at Dropbox, rising from the head of finance to CFO over his tenure and helping to take the company public in 2018 — is joining the Silicon Valley venture firm IVP in January.
It’s the realization of plans established long ago by Vashee, who fell in love with venture early on and has always known he wanted to return to it, though he wasn’t sure when or where that night happen. Indeed, he says that when he announced he was leaving Dropbox in early August to join the world of venture capital, he didn’t know where he would land. He instead “wanted my intentions out there.”
It was an effective tactic, from the sounds of things. Vashee hints that he talked with numerous firms, deciding that later-stage IVP was the best fit for a variety of reasons, including experience he’d gained at Dropbox helping to navigate the company through multiple stages of growth, including both as a private and then a public company.
Vashee also had experience working with IVP, which led Dropbox’s Series B round, and he says he saw firsthand the value the firm brings to a deal. “They helped us build our board, they were a sounding board for so many strategic decisions and always hustled for us.”
As an added bonus, he isn’t starting until January, giving him a little extra time to spend with his extended family in the Bay Area and, most importantly, with his young daughters, ages 4 and 1.
Vashee, who attended Columbia and headed to Morgan Stanley as an analyst right out of college, first fell in love with venture during his second job, which was as a senior associate with NEA, where he spent four years. “I absolutely loved investing and wasn’t planning to leave to join a company, but the opportunity to join Dropbox came up, and, knowing that I ultimately wanted to build a career as an investor, it if felt like something I couldn’t pass up.”
Though a generalist at NEA, Vashee says he will be focused on enterprise software — including companies focused on collaboration and finance automation — at IVP.
He suggests that he’ll also be spending a lot more time thinking about the going-public process, now that many choices are on the table in addition to traditional IPOs. Interestingly, he says that if he were taking Dropbox public today, an option like a direct listing is something he’d want to evaluate.
Unsurprisingly, he says a handful of IVP partners serve on the boards of companies that are right now evaluating tie-ups with special purpose acquisition companies, or SPACs, too.
In either case, he stresses that companies eyeing the public market need to be prepared, noting that the “operational readiness and rigor” that was instilled at Dropbox has proved “invaluable” to the company. Adds Vashee, “I don’t think the IPO process is broken, but has room for improvement.”
IVP announced its last fund — its biggest to date — in September 2017, closing at the time on $1.5 billion in capital. Given that three years have elapsed and that fund sizes have only continued to balloon (and that new partners are usually brought in just before a new fund closes), the firm appears poised to announce an even bigger vehicle any day now.
One of the firm’s highest-profile investors, Todd Chaffee, has already said that he won’t be actively investing in that new fund, following a 20-year run.