Early lessons from investing in Legion

Jonathan Pines
Webb Investment Network
3 min readOct 3, 2017

Our team was thrilled to see Legion’s launch and Series A announcement last week. Sanish has been quietly working on this company for 18 months, and it has been a pleasure getting to know him and the Legion team through WIN Labs¹ and later as a seed investment. Sanish was particularly thoughtful in how he got started, and we thought that we would share a few things we learned from seeing his approach to creating a new business:

  • Use what you already know. Before starting Legion, Sanish spent 15 years at Ariba / SAP building their procurement marketplace. During this time, he realized that he could apply similar principles to other types of marketplaces, such as labor and sourcing. He ended up deciding to address the hourly workforce, a topic that he cared about personally. Rather than search for a business idea, he went through the natural step of applying his existing knowledge to a problem that he cared about. Having this prior experience did not point to the exact product Legion is now launching, but it did provide him with a rich set of knowledge and relationships to draw from, as well as a high level of confidence in the overall direction.
  • Take your time with big decisions. Sanish had a clear direction early on, and he was impatient to get started. He quickly began research, customer interviews, and discussions with potential team members. At the same time, he was slower to move forward with product development and fundraising—until the right time. His first priority was to explore enough to have a clear picture of what he would build and why, and only then did he bring investors on board and shift his focus to writing software. This allowed him to approach fundraising from a position of strength, but more than that, to map out a clear path before making commitments to investors, team members, and customers — all of whom he will be working with for a long time.
  • Choose great partners and make them successful. Very early on, Sanish chose a design partner for his software — Philz Coffee — and put his entire focus on their needs. This paid off hugely, as they in turn helped him hone his product vision, test features with real users, roll out a significant deployment over time, and showcase the Legion product in a blog post about using technology to build an empowered workforce. This hand-in-hand development resulted in a product that actually solves what it is supposed to, and that can now work for many other customers in the same way—and turned a customer into a champion for Legion.

We look forward to Legion’s continued progress, and to more lessons ahead on their quest!²

For more information on how Legion helps companies with an hourly workforce, visit their website at legion.co or their jobs page here.

(1) WIN Labs is our new program to help founders get started with 3–6 months of help from Maynard and our Affiliate Network. Our first groups include Koan and Elevate Security as well as Legion.

(2)

Legion Quest Part 1

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