What happened

Five days ago, shares of e-signature company DocuSign (NASDAQ:DOCU) got shredded after an earnings report showed that its business, which was proceeding just fine in Q3, is about to take a turn for the worse in Q4.

Two days ago, famed tech investor Cathie Wood stepped up to snap up DocuSign shares amid the sell-off, helping to salvage the stock.

And today? Today, DocuSign stock is recovering even further -- up 5.5% as of 10:20 a.m. ET -- on news that Cathie Wood isn't the only investor who believes DocuSign is a bargain.

Stock up glowing green arrow climbs on a stock screen

Image source: Getty Images.

So what

Our latest contestant in this game of "How Much is DocuSign Really Worth?" is none other than DocuSign CEO Daniel Springer himself. Because as StreetInsider.com reports today, Springer went shopping for cheap DocuSign shares on Tuesday, spending $5 million to acquire a total of 33,675 shares at prices ranging from $138.93 to $146.91.

Now what

While we don't know for certain what motivated Springer to make his purchases, the logical assumption is probably the right one: Like most investors, he bought shares of DocuSign because he thinks they are undervalued and are going to go up over time.

You can of course disagree with him about that. With a market capitalization of $29 billion and negative earnings according to generally accepted accounting principles (GAAP), DocuSign isn't the most obvious value stock on the market. Then again, DocuSign did generate $418 million in positive free cash flow over the last 12 months and, according to analyst estimates collected by S&P Global Market Intelligence, the company is on track to more than triple that figure over the next five years, generating FCF of nearly $1.4 billion in 2026.

If you think buying DocuSign for less than 21 times FCF five years from now is a good deal, then you might want to join Cathie Wood and Daniel Springer and pick up a few shares yourself.


This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.