-81%

est. 2Y upside i

AI & MLSeries A

Willow is a voice dictation app that lets you type anywhere on your computer using your voice. People already rely on Willow every day to write emails, respond in Slack, prompt AI, and move faster in their day-to-day work.

Rank

#3856

Sector

AI Productivity Software

Est. Liquidity

~6Y

Data Quality

Data: Medium

Willow operates in a rapidly growing AI productivity market with a differentiated product offering superior accuracy and personalization.

Last updated: March 10, 2026

Bull (15%)+300%

Willow achieves significant market penetration by leveraging its superior accuracy, context-awareness, and personalization to become the preferred AI dictation tool for professionals, expanding successfully into Windows and developer workflows. This drives rapid revenue growth, justifying a $100M+ valuation (4x current) within two years.

Base (20%)+50%

Willow continues to grow steadily, capturing a niche in the professional dictation market with its differentiated features, but faces persistent competition from incumbents and well-funded startups. It achieves moderate user adoption and revenue growth, leading to an exit at a $37.5M valuation (1.5x current).

Bear (65%)-80%

Dominant incumbents like Apple and OpenAI integrate advanced dictation features directly into their platforms, commoditizing Willow's offering and limiting its market share. This leads to stalled growth and a down round or acquisition at a $5M valuation (-80% from current), significantly impacting common stock value.

Est. time to liquidity~6.0 years

Preference Stack Risk

high

Investors hold $5M in liquidation preferences, which represents 20% of the estimated $25M current post-money valuation.

Dilution Risk

high

As an early-stage company, Willow will likely require several more funding rounds, leading to significant future dilution for common shareholders.

Secondary Liquidity

none

There is no active secondary market for shares in a company at this early stage.

View all 4 open roles at Willow →

Last updated: February 17, 2026

Questions to Ask at the Interview

Strategic questions based on Willow's data — designed to show you've done your homework.

  • 1

    “Given the strong incumbent threat from companies like Apple and OpenAI, how does Willow plan to maintain its competitive moat and avoid commoditization of its core dictation features?”

  • 2

    “With a focus on expanding to Windows and developers, what are the key metrics and milestones the company is tracking to demonstrate successful market penetration and adoption in these new segments?”

  • 3

    “Considering the early stage of funding and the likely need for future rounds, how does the company envision the path to a liquidity event for employees, and what are the current thoughts on dilution and secondary liquidity?”

Community

Valuation Sentiment

Our model estimates -81% upside. What do you think?

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Disclaimer: This analysis is AI-generated and does not constitute financial or career advice. Always conduct your own due diligence.