Smartsheet CEO Sells Shares Valued at Over $1 Million

Smartsheet Inc., a leader in cloud-based work management platforms, has reported a notable transaction by its President and CEO, Mark Mader. In a recent SEC filing, it was disclosed that Mader sold 20,000 shares of Class A Common Stock at a price of $51.78 per share, totaling over $1 million.

This sale occurred on September 19, 2024, and was executed under a Rule 10b5-1 trading plan that Mader had established on March 27, 2024. Such plans permit company insiders to arrange pre-approved trading schedules for selling stocks, which helps protect them from allegations of insider trading.

Despite the sale, Mader retains a substantial interest in the company, holding 588,762 shares of Smartsheet’s Class A Common Stock directly. He also has indirect holdings through trusts for his children, which comprise 51,250 shares in the T49C Trust and 40,000 shares in the L38 Trust. It is essential to note that Mader disclaims beneficial ownership of these indirect holdings, as they are managed by Douglas Porter, the trustee of the trusts.

Investors are typically attentive to the trading activities of company insiders, as these can offer insights into their views on the company’s valuation and future potential. Consequently, Smartsheet’s stock performance and the CEO’s transactions are expected to be closely analyzed by market participants.

In other company news, Smartsheet has reported a 17% rise in both revenue for the second quarter and annualized recurring revenue (ARR), reaching $276.4 million and $1.093 billion, respectively. The introduction of a new pricing model has led to significant customer engagement, resulting in a 50% increase from the previous year in customers with an ARR exceeding $1 million, now totaling 77.

Looking ahead, Smartsheet projects its revenue for fiscal year 2025 to fall between $1.116 billion and $1.121 billion, along with an increase in free cash flow to $240 million. Additionally, the company is undergoing a transition in its executive structure, with Chief Operating Officer Stephen Branstetter resigning to take on an advisory role until November 18, 2024. The company is adopting a dual President model that will include Presidents for Go-to-Market and for Product & Innovation.

Furthermore, Smartsheet is reportedly in discussions to explore acquisition opportunities with a private equity group, as stated by KeyBanc Capital Markets, which holds a Sector Weight rating on the company. KeyBanc’s analysis suggests a fair value of approximately $50 per share for Smartsheet, indicating possible upside in the event of a private equity deal. These initiatives form part of the company’s ongoing goals to expand and enhance its operational strategies.

As Smartsheet Inc. navigates the evolving cloud-based work management sector, recent insider transactions have highlighted the company’s financial situation and future directions. Key metrics show that Smartsheet has a market capitalization of $7.14 billion, signifying its strong industry presence. The company is enjoying robust revenue growth, with a 20.16% increase over the past twelve months as of Q2 2025, accompanied by an impressive gross profit margin of 81.61%.

From an investment perspective, Smartsheet’s balance sheet reveals more cash than debt, suggesting financial stability and prudent management. Additionally, analysts have raised their earnings forecasts for the upcoming period, with expectations for the company to achieve profitability this year. These positive indicators are reflected in the company’s stock, which is currently trading near its 52-week high, demonstrating a solid return over the last three months.

For investors considering Smartsheet’s stock, these insights point to a company that is on an upward trajectory, backed by sound financial practices and promising growth potential, despite recent insider sales. Additional insights and analysis are available for those looking for more information to aid in their investment decisions.