The past six months have been exceptionally challenging for C3.ai (NYSE: AI), a provider of enterprise artificial intelligence software. The stock has declined by 41% over this period, currently trading at $9.21 per share—a sharp pullback that has left many shareholders reassessing their positions. The downturn was precipitated in part by the company’s softer-than-expected quarterly results, prompting investors to weigh whether the current valuation represents a potential buying opportunity or a signal to exit.

Why Do We Think C3.ai May Underperform?
Despite the stock’s decline to a more attractive entry price, our analysis suggests caution. While the company operates in a high-growth sector, several fundamental concerns warrant a skeptical outlook. Below are three key reasons to approach C3.ai with caution, along with an alternative stock we believe offers a more compelling risk-reward profile.

1. Declining Billings Signal Weakness in Product Adoption and Sales Execution
Billings—a non-GAAP metric often referred to as “cash revenue”—provides insight into the actual cash collected from customers during a given period. Unlike revenue, which is recognized incrementally over the duration of a contract, billings reflect the company’s near-term ability to generate cash from new and existing customer relationships.

In the fourth quarter, C3.ai reported billings of $58.57 million. More concerning, the company has averaged an 11.2% year-over-year decline in billings over the past four quarters. This sustained contraction is an underwhelming indicator, suggesting that C3.ai is facing headwinds in both customer acquisition and retention. The trend may also point to intensifying competitive pressures or potential market saturation within the enterprise AI space—a troubling sign for a company that has long positioned itself as a leader in the sector.

2. Low Gross Margin Reveals Underlying Structural Profitability Challenges
For software companies, gross profit represents the residual revenue after accounting for the direct costs of delivering products and services, such as cloud infrastructure, third-party licenses, and certain personnel expenses. In the software industry, these costs are typically low relative to revenue, which explains why established software firms often command premium valuations and generate substantial operating leverage.

C3.ai, however, exhibits a gross margin profile that lags significantly behind most software peers. Over the past year, the company has averaged a gross margin of just 43.5%. To put this in perspective, this means that for every $100 in revenue, C3.ai incurs approximately $56.48 in direct costs—a figure that reflects comparatively high infrastructure expenses relative to asset-light software models such as ServiceNow.

Beyond the current margin level, the trajectory of gross margins is equally important. Expanding gross margins can provide the financial firepower needed to invest in growth and generate sustainable profitability. In C3.ai’s case, gross margins have contracted by 15.3 percentage points over the last two years, representing one of the steepest declines in the software sector. This erosion raises questions about the company’s pricing power, operational efficiency, and long-term unit economics.

3. Projected Decline in Free Cash Flow Margin Adds to Concern
Free cash flow is a critical metric for assessing a company’s financial health, as it represents the actual cash generated from operations after capital expenditures. Unlike accounting profits, which can be influenced by non-cash items and accruals, free cash flow provides a clearer picture of a company’s ability to fund operations, invest in growth, and return capital to shareholders.

Looking ahead, analysts project that C3.ai’s cash flow position will deteriorate further. Consensus estimates indicate that the company’s free cash flow margin—which stood at negative 41.3% over the trailing twelve months—is expected to fall to negative 50.2% over the next year. This projected widening of cash burn suggests that the company may need to rely on existing cash reserves or additional financing to sustain its operations, introducing further uncertainty for investors.

Final Assessment: Proceed with Caution
Taken together, these factors paint a concerning picture. C3.ai is grappling with declining billings, structurally low and contracting gross margins, and a worsening free cash flow outlook—all of which raise doubts about its ability to achieve sustainable profitability in the near to medium term.

Following the recent decline, the stock now trades at approximately 6.2 times forward price-to-sales, with a share price of $9.21. While this valuation is more modest than during previous highs, it still embeds expectations for a significant operational turnaround. In our view, the combination of fundamental weaknesses and competitive pressures suggests that there are more attractive opportunities elsewhere in the market. Investors may be better served by focusing on companies with stronger unit economics, clearer paths to profitability, and more consistent operational execution.