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We invest in retail focused
technology companies


About Us

Otimo Retail, an investment vehicle backed by Howard Stotland, Matthew Stotland, and David Henning provides capital, strategic and operational guidance to small and mid­-sized technology providers who develop, market and sell software solutions to retail organizations.

Our Mission

To be clear, we are not a venture capital fund. We are a growth stage investor in retail focused technology companies. As investors, we want to be owners, side by side with entrepreneurs. We believe it is important for retailers to invest in world­class technology solutions in order for their businesses to thrive. We look to invest in these innovative companies.


Value Add

We strive to add perceivable value to all of our investments and offer the following services:

  • Make introductions to appropriate C-­level executives at Fortune 500 retailers.
  • Help attract and recruit talent in sales, marketing, development, product management and professional services.
  • Use our industry knowledge to help clarify strategic direction. 
  • Assist in defining appropriate key metrics. 
  • Tap our network of retail technology companies for partnership and business development opportunities.

Otimo Retail Team


Howard Stotland

Educated at McGill University and the Massachusetts Institute of Technology, retail technology visionary Howard Stotland founded STS Systems in 1973, a leading provider of information systems to the petroleum and retail industries. Read More →


Matthew Stotland

Matthew graduated in 2006 with a degree in Computer Science from Boston University. He was the co-­founder of the Yellow Bird Project, a retail organization centered around products designed by musicians and many of its retail goods are now associated with charitable endeavours. Read More →


David Henning

David has a long history in Retail Technology both as a C-level Executive and as a hands-on developer. Early in his career, David pioneered the development of a Point-of-Sale Solution for Windows-based PC’s, created automated Distribution and Warehouse Management Systems, and a host of other state-of-the-art technology for retailers.  Read More →


Portfolio Companies