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Benjamin J Gilbert


Ben PSL HeadshotBen is the Co-Founder of Pioneer Square Labs in Seattle, WA. Ben previously co-founded Madrona Venture Labs, spinning out MightyAI and ReplyYes. He also ran The Garage, Microsoft’s Grassroots Innovation program. He worked as the Program Manager on the user experience of the first version of Office for iPad. Ben was named the 2017 Young Entrepreneur of the Year by GeekWire, and is the co-host of the popular podcast, “Acquired.”

He has a BS in Computer Science and Engineering from The Ohio State University.

LinkedIn | Twitter

Previous Projects


ReplyYes April 15 – September 15

ReplyYes is the easiest way to shop. No apps, no web pages. We connect our members with the things they love, every day, with a simple text. Using scalable text experiences coupled with personal interaction, we’re creating the best conversations in commerce. It is the second company to come out of Madrona Venture Labs.


  • Initial Web and Back-End Development
  • Project Management
  • Online Marketing


Spare5 (Now MightyAI) April 14 – March 15

Spare5 is designed to be the default “do work now” app for every smartphone owner on the planet. It is the first company to come out of Madrona Venture Labs. A tremendous opportunity exists to better people’s lives by making time they spend on mobile devices more valuable. A host of companies can benefit immediately by tapping the nearly unlimited resource of people’s time and expertise to improve their data and understanding of their customers. We are bringing them together.


  • iOS Development
  • Project Management
  • Business Development
  • Data Monkey



Office for iPad Spring 12 – Spring 13

Microsoft Office for iPad brings the full power of Word, Excel, and PowerPoint to the iPad in a touch-first way, designed and developed natively for the iPad.


  • Search Experience
  • Ribbon and Galleries
  • “Create New” Experience
  • Product Activation & First Run Experience
  • Text Selection UX
  • Word Ruler


Red Ride Summer 13 – Winter 13

Red Ride is a app to aggregate all of the ride sharing options in your city such as Uber, Sidecar, car2go, etc. It allows you to quickly see which option is the fastest way to move around your city.


  • iOS Development
  • Product Direction
  • Business Development

OneNote for iOS Fall 12 – Spring 13

Microsoft OneNote for iPhone and iPad is your digital notebook for capturing what’s important in your personal and professional life. Jot down your ideas, add pictures, update your shopping list, and check your to-do’s from this Microsoft Office app.


  • Program Management:
    • Commanding Space, Ribbon
    • Search
    • User Experience
    • Notebook Management
    • Microsoft App Ecosystem Interoperability
    • First Run Experience




Zero Winter 10 – Winter 11

Functional Delights’s second app, Zero is a minimalist and beautiful reminder-based to-do list for the iPhone with cloud sync to iCal. More information is available here.


  • User Experience (product design, feature set)
  • Python Cloud Sync Infrastructure
  • Back End User Management




DryerBro Winter 10

DryerBro alerts you when your laundry’s done using the iPhone’s accelerometer. More information is available here.


  • Project management
  • Javascript (Build with Appcelerator Titanium)
  • Copywriting




SeizeTheDay Summer 09 – Summer 11

I formed Functional Delights, LLC with Ian Kono in September of 2009. We launched SeizeTheDay, an iAd-supported reminder-based task manager for the iPhone in July of 2010. More information is available here.


  • iOS Development
  • App Design




HackerFollow Fall 10

HackerFollow “Twitterizes” HackerNews. It allows you to follow a set of HackerNews users’ submissions and comments.


  • Design
  • Front End Development
  • Back End PHP Scraper Development


It’s This For That Summer 10

A satirical site which generates startup pitches.


  • This
  • That