Willow

What do they actually do

Willow makes a voice-first typing tool that works across the apps you already use. On Mac, it lets you place your cursor anywhere and speak to produce clean, formatted text with low latency. On iPhone, Willow offers a voice keyboard that transcribes your speech in any app and lets you make quick in-keyboard edits; it supports custom vocabulary and multiple writing styles (TechCrunch, Willow site).

The product focuses on accuracy, automatic punctuation/formatting, and personalization, with team features like shared dictionaries. For organizations, Willow offers enterprise controls and compliance (SOC 2 Type 2, HIPAA) via its Team and Enterprise plans (Willow Help Center – Pricing Plans, Willow use case page). Today it’s available on Mac and iOS; the company has publicly noted plans to expand to Windows and Android (TechCrunch, Willow Help Center).

Who are their target customer(s)

• Managers and other knowledge workers buried in email and chat: They lose hours to typing, moving context between apps, and formatting messages. They want to speak quick replies and get clean text anywhere they type so they can move faster (YC profile).
• Founders and product people who iterate with AI tools and prompts: Switching between keyboards, chat windows, and prompt edits breaks flow. They want a faster input to draft and refine prompts so ideas keep moving (YC launch post).
• Sales and customer-facing reps working across email/Slack/CRM: They need rapid, consistent replies but spend time retyping similar messages. They want to dictate replies and update CRM text without manual typing to maintain response speed (YC profile).
• Developers and engineers writing docs, prompts, and boilerplate: Long typing sessions add friction and strain; generic dictation mishears technical terms. They want better accuracy for programming terms and low-latency speech-to-text that fits coding and prompting workflows (Willow blog).
• Teams and enterprises needing accuracy, shared vocabulary, and data controls: They can’t accept sloppy transcription or unmanaged data. They need custom team dictionaries and compliance (SOC 2/HIPAA) with admin controls (TechCrunch, Willow site/help).

How would they acquire their first 10, 50, and 100 customers

• First 10: Founder-led outreach to YC peers and operator/developer networks; onboard each early user 1:1 and ship fixes directly from their feedback to validate core workflows (YC profile, Willow blog).
• First 50: Turn early wins into short case studies and referrals; run targeted outreach to managers, sales reps, and founders in LinkedIn/Slack communities; host demos showing spoken replies in email/CRM and add templates for common workflows (YC launch post).
• First 100: Lean on distribution (Mac app, iOS keyboard; Windows/Android on roadmap) and partnerships with CRM/sales/dev tools; begin small team plans highlighting shared dictionaries and compliance to land teams that need accuracy and controls (TechCrunch, Willow site/help).

What is the rough total addressable market

Top-down context:

Willow sits inside the broader voice and speech recognition market, which analysts size in the low tens of billions today with projections to exceed $50B by 2030 (Grand View Research, MarketsandMarkets).

Bottom-up calculation:

A practical seat-based view uses knowledge workers who write often. For example, if Willow converts 1% of ~71.5M U.S. management/professional workers to an Individual plan at ~$15/month, that’s ~715k users and ~$128M ARR; enterprise/team seats increase ARPU and accelerate revenue (BLS via Upwork, Willow pricing/help).

Assumptions:

• Only a subset of global email users/labor force are likely paid adopters; focus is on high-frequency writers and enterprise buyers (Radicati, World Bank/ILO).
• Conversion rates are illustrative (e.g., 1–5%) and scale linearly in the scenario math.
• Pricing based on current published plans (Free, Individual ~$15/mo, Team ~$12/user/mo, Enterprise custom) (Willow pricing/help).

Who are some of their notable competitors

• Apple Dictation (iOS/macOS): Free, built-in dictation on Apple devices. Ubiquitous and convenient but generally lacks advanced workflow features, team dictionaries, and enterprise controls compared to specialized tools.
• Google Voice Typing (Gboard/Google Docs): Free voice typing in Google Docs and Android via Gboard. Broad availability with basic editing by voice, but limited to Google surfaces and not tailored for enterprise compliance.
• Nuance Dragon (Microsoft): Longstanding enterprise-grade dictation (healthcare/legal variants, Windows-first). Known for custom commands and accuracy; strong in regulated industries but heavier and pricier than modern lightweight apps.
• Wispr Flow: Direct competitor offering cross-app voice typing and mobile keyboard with team features; well publicized and positioned for professionals and teams (TechCrunch mentions).
• Superwhisper: Whisper-based dictation popular on Mac/iOS with offline options. Appeals to privacy-conscious users and developers, though it may require more setup versus turnkey tools.