Twitter (NYSE:TWTR) just lost two more top executives.

The company's VP of finance, Celia Poon, who has been at the company for four years, will leave in August. VP of live video engineering Jeremy Rishel -- who joined Twitter four years ago with the acquisition of social analytics company Bluefin Labs -- left on June 16.

Poon's departure is troubling, because she took on some of CFO Anthony Noto's responsibilities after he assumed the dual role of CFO and COO last November. David Aufderhaar, Twitter's VP of corporate finance, will replace Poon, but it seems doubtful that he can also cover Noto's CFO responsibilities. This means that Noto will likely need to cover both positions until a permanent CFO can be named.

A man logs on to Twitter's app.

Source: Pixabay.

Rishel's departure also raises red flags, because live video is one of Twitter's core pillars of growth. Rishel was reporting directly to Periscope CEO Kayvon Beykpour, who oversaw the integration of the streaming app into Twitter over the past year. However, the live video business looks less wobbly than the CFO seat -- Twitter recently hired former Bloomberg exec Todd Swidler to run the unit's live video partnerships.

Why can't Twitter keep its top executives?

Twitter started losing executives at an alarming rate after co-founder Jack Dorsey returned as CEO in late 2015. That long list includes its heads of media, engineering, commerce, human resources, online sales, and consumer product; the directors of its businesses in India (including Southeast Asia and the Middle East) and China; and COO Adam Bain and CTO Adam Messinger.

Those departures were likely caused by several problems. Twitter's plummeting stock price and anemic user growth likely sapped employee morale. Back in 2015, a Twitter insider told Business Insider that "the wheels are off the bus," and that morale was "beyond low." The constant departures of its consumer product chiefs also likely produced unfocused initiatives for its ad business and ecosystem growth.

Twitter's mobile app.

Twitter's mobile app. Source: Google Play.

Meanwhile, Dorsey split his time as the CEO of both Twitter and online payments company Square (NYSE:SQ). Many of Dorsey's initiatives at Square have paid off, but his plans at Twitter -- which mostly focused on curated Moments, live video partnerships, and divesting non-core businesses -- haven't brought back users or advertisers. Instead of stepping down from Square and working full-time at Twitter, Dorsey started several rounds of layoffs -- which likely resulted in even lower morale.

Dorsey was previously ousted as CEO in 2008, reportedly due to poor management and communication skills. Some optimists heralded his return as a "Steve Jobs" moment, but the ongoing executive exodus suggests that Dorsey still can't keep the wheels on his bus.

What does this mean for investors?

All these management issues are spooking company insiders. Over the past three months, Twitter's insiders sold 2.34 million shares on the open market and only bought about 656,000 shares. Back in April, co-founder and former CEO Evan Williams -- who clashed with Dorsey in the past -- announced that he would sell up to 30% of his shares over the following year.

The future of Twitter's management looks bleak. There's a CEO who splits his time with Square, a CFO who is also the COO, a corporate finance VP who must cover another VP's job and possibly assume some CFO responsibilities, and a streaming video CEO who just lost a key engineer. Meanwhile, Twitter's new head of product, Keith Coleman, barely even uses Twitter, with fewer than 500 tweets. Kevin Weil, who held the position from 2014 to 2016, tweeted over 16,600 times.

These problems can't be fixed overnight, but a full-time CEO could at least point Twitter in the right direction. The recent return of co-founder Biz Stone, who stated that his job would be to "guide the company culture," might help stop Twitter's brain drain. But it could also just be a symbolic gesture -- like Dorsey's #LoveTwitter insider purchases -- which fails to fix the social network's deepening problems.

Leo Sun has no position in any stocks mentioned. The Motley Fool owns shares of and recommends Twitter. The Motley Fool has a disclosure policy.