Over the last year, that has been only one insider at Upwork to sell their shares, Senior Vice President of Product & Design Hayden Brown.   Brown sold $757k worth of shares which represented approximately 15.7% of Hayden Brown’s holding.

What Is Insider Buying and Selling?

It’s quite normal to see company insiders, such as board members, trading in company stock. However, such insiders must disclose their trading activities, and not trade on inside information.

We would never suggest that investors should base their decisions solely on what the directors of a company have been doing.  But logic dictates you should pay some attention to whether insiders are buying or selling shares. For example, a Colombia University study found that ‘insiders are more likely to engage in open market purchases of their own company’s stock when the firm is about to reveal new agreements with customers and suppliers’.

Given the new partnership between Microsoft and Upwork, along with the potential for an acquisition to transpire, it would make sense that management is holding its shares across the board.

Additionally it is quite possible that Upwork will significantly beat its earnings expectations due to the following reasons:

1.  Upwork has received considerable publicity over its IPO, resulting in new businesses and freelancers joining the Upwork platform.
2. Upwork has hired an enterprise sales team to connect more Fortune 500 businesses to Upwork, which are historically proven to spend the most money on the platform.
3. Microsoft partnered with Upwork to start offering Upwork's services to enterprise clients in Microsoft's network.
4. Upwork has launched a national ad campaign to raise awareness around the platform.

Earnings announcement for UPWK is on Feb 06, 2019.   Till then we'll just have to wait and see.

Disclaimer: As a company that uses Upwork on a daily basis, many of us freelancers have made an investment in UPWK.   We believe in the platform fully.