Mission Trail Capital Takes 5% Stake in Sidetrade, Second US Investor to Build Significant Position in Under Three Months

Texas-based hedge fund specializing in software and technology investments acquires 5.39% stake in AI-native Order-to-Cash platform Sidetrade.

Mar. 24, 2026 at 7:12am

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Sidetrade, the AI-native Order-to-Cash platform recognized as a Leader in the Gartner® Magic Quadrant™, announces that Mission Trail Capital Management LLC, a Texas-based hedge fund, has acquired 80,659 shares representing 5.39% of the company's outstanding share capital. This move makes Mission Trail Capital Management the second US-based investment firm to cross a major ownership threshold in Sidetrade in less than three months, following New York-based Briarwood Chase Management doubling its position to over 10% of capital in March 2026.

Why it matters

Sidetrade operates at the intersection of AI and enterprise finance, with its platform intelligently automating the Order-to-Cash processes for large enterprises. The company's unique billing model based on transaction volume, rather than per-user license fees, eliminates the AI cannibalization risk that the market is applying broadly to software valuations, making it an attractive investment opportunity.

The details

Mission Trail Capital Management, LLC (MTCM) is an Austin, Texas-based investment manager focused on leading software companies. The firm's concentrated portfolio construction allows it to conduct deep fundamental due diligence that frequently spans several years with a long-term investment horizon. Joshua Braden, Founder of Mission Trail Capital Management, cited Sidetrade's proprietary data advantage, AI-native architecture, and significant customer value as key factors behind the investment.

  • On March 3, 2026, New York-based Briarwood Chase Management disclosed it had doubled its position to over 10% of Sidetrade's capital.
  • Mission Trail Capital Management acquired 80,659 shares, representing 5.39% of Sidetrade's outstanding share capital, in March 2026.

The players

Mission Trail Capital Management LLC

A Texas-based hedge fund specializing in software and technology investments.

Joshua Braden

The Founder of Mission Trail Capital Management.

Sidetrade

An AI-native Order-to-Cash platform recognized as a Leader in the Gartner® Magic Quadrant™.

Briarwood Chase Management

A New York-based investment firm that doubled its position in Sidetrade to over 10% of capital in March 2026.

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What they’re saying

“We are thrilled to invest in Sidetrade. We have known Olivier Novasque and his team for many years and admire the ambitious, thoughtful way they built this company to deliver measurable customer value. In our numerous conversations with Sidetrade's customers, we heard consistent reports of significant working capital improvements, particularly decreased DSOs, following Sidetrade's implementation. By investing in a proprietary Data Lake and embedding AI into their roadmap years before it became a buzzword, the team demonstrated a long-term commitment to superior customer outcomes leveraging cutting edge technologies. We look forward to supporting their continued growth.”

— Joshua Braden, Founder of Mission Trail Capital Management

What’s next

Sidetrade is set to publish its annual results for 2025 on March 30, 2026, after the stock market closes. The company will also unveil its new strategic plan 'O2C Intelligence 2030' on April 7, 2026, after the stock market closes, and release its first-quarter revenue for 2026 on April 14, 2026, after the stock market closes.

The takeaway

Sidetrade's unique business model, AI-powered platform, and strong customer traction have made it an attractive investment for US-based hedge funds like Mission Trail Capital Management and Briarwood Chase Management, highlighting the growing interest in AI-driven enterprise software solutions that can drive tangible business outcomes.