In a surprising turn of events, workplace communication company Slack has experienced the departure of three chief executive officers (CEOs) in less than a year. Following its acquisition by Salesforce for $28 billion in 2020, the executive shuffle has raised questions about the stability of the company's leadership.

The most recent addition to the corner office is Denise Dresser, who assumed the role in November. Despite acknowledging the difficulty of stepping into the position amidst such circumstances, Dresser expressed confidence in her ability to lead. With a background in accounting and over a decade at Salesforce in various executive roles, Dresser is focused on building upon her predecessors' work while injecting her own personality into the role.

Dresser's predecessor, Lidiane Jones, lasted only 10 months in the position before leaving to become the CEO of Bumble. Jones had taken over from Slack co-founder Stewart Butterfield, who announced his departure at the end of 2022. While replacing a founder-CEO is challenging, stepping into the role just months afterward adds further complexity. Analysts, however, view some executive turnover as natural following an acquisition, as the company seeks to establish its place within the larger Salesforce ecosystem.

Slack's performance since the acquisition has drawn attention. The company's revenue growth has significantly slowed, with a drop from 46% year-over-year in Q3 2023 to a mere 16% in Q4 2024. Dresser's primary challenge lies in reversing this downward trend. To achieve this, Slack must identify new business opportunities while ensuring customer satisfaction, without becoming overly reliant on Salesforce integration and alienating non-Salesforce customers.

Addressing the delicate balancing act, Brent Leary, a principal analyst at CRM Essentials, emphasized the need for Dresser to establish Slack as a standalone brand that appeals to a broader customer base, while also facilitating seamless collaboration for Salesforce users. Dresser remains optimistic, citing the original vision of the two companies coming together and the potential to nurture and continue Slack's success.

One significant change that Dresser will navigate is the integration of generative artificial intelligence (AI) across Slack and the Salesforce product line. Leveraging Slack's unstructured data and Salesforce's vast customer data, AI has the potential to enhance knowledge sharing and improve collaboration. Dresser highlights the ability of AI summaries to expedite her learning process, saving time and providing valuable insights.

Competing with Microsoft, which offers Teams alongside Office 365, Dynamics 365, and AI-powered Microsoft Copilot, presents another hurdle for Dresser. However, analysts suggest that Slack's advantage lies in its interoperability and ease of use. While Microsoft may have distribution advantage, its ecosystem dependency limits its flexibility.

Adding complexity to Dresser's responsibilities, CTO Cal Henderson, one of Slack's co-founders, recently departed and was replaced by Salesforce co-founder and CTO Parker Harris. Dresser acknowledges the challenges ahead and emphasizes the importance of building connections with employees and customers, confident that her passion for making a positive impact on the world will guide her through this critical phase for Slack and its position within the broader Salesforce ecosystem.

As Slack strives to regain growth momentum and navigate the dynamic landscape of workplace communication, all eyes remain on Dresser and her ability to lead the company forward. With a combination of strategic decision-making, innovative integration, and a focus on fostering human connections, the future of Slack within the Salesforce family awaits its next chapter.