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Hemingway Editor Plus

I co-founded Hemingway Editor and Wrangle. At Hemingway, I lead product, design, and engineering across our free writing editor, desktop app, and AI subscription product. Our free product reached 3–4 million annual visitors at its peak, and our AI writing features have served tens of thousands of monthly active users. My work includes prompt engineering, fine-tuning, evaluations, and automation that helps a two-person business serve its customers.

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Hemingway Editor with highlighted writing issues and readability feedback

Hemingway Editor with highlighted writing issues and readability feedback

Hemingway’s editor highlights complex sentences and writing issues alongside readability feedback.
Hemingway AI before-and-after example simplifying a wordy paragraph

Hemingway AI before-and-after example simplifying a wordy paragraph

AI rewriting example captured from Hemingway’s official feature page.Hemingway Editor Plus features
Animated demo of our latest inline writing feedback feature.

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My role

Co-Founder · May 2014–present

I built Hemingway Editor, an AI-powered writing assistant used by millions each year. With just two cofounders, we grew it to $1mm a year in revenue, with thousands of paying customers. I designed it, built it, shipped production AI features, A/B tested experiments, did prompt engineering and evals, and helped market it. Hemingway Editor has been #1 on Hacker News and was covered by the New Yorker, NPR, Fast Company, and more.

Achievements

  • Co-created a freemium writing product that reached #1 on Hacker News, earned coverage from The New Yorker, NPR, Esquire, and Fast Company, and grew to approximately 3–4 million annual visitors at peak.
  • Led product, design, and engineering for Hemingway Editor Plus, extending the editor into an AI-powered subscription product with a two-person team.
  • Shipped LLM-powered writing features serving tens of thousands of monthly active users. Improved text simplification and rewriting through prompt engineering, fine-tuning, AI evaluations, and user preference testing.
  • Built a support agent covering more than 20 scenarios, including refunds, cancellations, and custom invoicing through payment confirmation and account activation.

Skills used

  • Product Management
  • Product Strategy
  • Software Development
  • Generative AI
  • Prompt Engineering
  • Model Evaluation
  • Software as a Service
  • User Experience
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