What Happened Before IPO? OpenAI Loses Two Top Executives in Days

OpenAI's senior leadership is once again in flux. On Thursday (13th), the company announced that Denise Dresser, its revenue chief who joined only in December last year, will leave before completing one year in the role to pursue other opportunities. She will be succeeded by Dali Rajic, President and COO of Wiz, a cybersecurity firm backed by Google's parent company Alphabet. This marks the second top-level executive departure at OpenAI within days, drawing significant attention as the company prepares for its initial public offering (IPO) and faces rising competition in the enterprise market.

Dresser will remain temporarily during a short transition period to assist the business team in serving clients and to work with OpenAI President Greg Brockman to complete the handover. In a LinkedIn post, she said it was "incredible" to have been personally involved in one of the world's most transformative technologies and expressed pride in the team's achievements and mutual support.

Dresser previously served as CEO of Slack and held executive roles at Salesforce (CRM-US) for over a decade. She was hired at the end of last year to lead OpenAI's revenue operations. With extensive experience in enterprise software and customer development, she was expected to help OpenAI expand its enterprise market presence and compete with key rival Anthropic. In April, she also took on some responsibilities from senior executive Brad Lightcap after he moved to lead "special projects."

However, Lightcap himself announced earlier this week that he is leaving OpenAI after eight years to start his own company. Prior to that, product and business head Fidji Simo stepped down last month due to a severe worsening of a chronic illness; former Chief Product Officer Kevin Weil also left in April. These consecutive departures make new revenue chief Rajic one of the first major executive appointments since Brockman expanded his managerial authority.

Brockman stated that the way AI technology is deployed is changing rapidly, and Rajic will help transform the company's accumulated experience into repeatable operational models. In an internal memo, he noted that OpenAI's annualized revenue grew over 20% month-on-month in July, with enterprise customer business growing 32%. The company believes the next phase must focus on proving that every dollar customers invest delivers measurable business value.

Rajic excels at building organizations centered on customers and data metrics. His cybersecurity background is also seen as a key advantage, as enterprises increasingly prioritize risks related to cyberattacks and defense when adopting more powerful AI models.

OpenAI is fiercely competing with Anthropic for enterprise clients. Anthropic has risen quickly with tools tailored for complex tasks like programming and earlier this year briefly surpassed OpenAI in valuation, potentially going public as early as this fall. OpenAI, meanwhile, continues promoting its AI agents, including the programming tool Codex, and has lowered prices on some models to counter Anthropic and Chinese competitors.

OpenAI secretly filed its IPO documents with the U.S. Securities and Exchange Commission (SEC) in June, with a fundraising valuation reaching $852 billion in March. As the company prepares for Wall Street scrutiny, stabilizing its management team, sustaining rapid growth, and demonstrating the profitability potential of its enterprise AI business will be key focal points for investors.