Shortly after I joined FiveStars as head of design in June of 2015, we as a leadership team decided that we would raise a Series C starting on day 1 of Q4. Q3 would be dedicated to preparing for fundraising. What the product development organization committed to was to design and develop three cutting-edge functional pilots, to be deployed live by October 1 in several key customer locations, such that potential investors could try our latest technology out, and experience our strategic direction.

For the consumer mobile application, the key thing we had to demonstrate was that we could deploy Bluetooth beacons in store, and incorporate this technology into our discovery experience for new customers of that store, as well as automatic check-in for existing members of the loyalty program of that store.

For the Customer Touchscreen (CTS), our key demonstration points were a vertical design that took up less counter space, as well as innovations in attraction/discovery and new customer signups. The third pilot was for the Cashier product installed at the point of sale.

When we decided to do this, the team was too small and too junior to deliver that much new software in that timeframe and have it be awesome. Also, as a company, we already knew a lot about the Merchant persona, since that's the person making the buying decisions, but very little about the Cashier or the Consumers, for whom all our new innovations would be targeted. 

My challenges as a leader were threefold: 

1) Build up a team fast enough and strong enough to deliver all this work on time

2) Make sure the work was as awesome as possible, and that our evaluation criteria were clear

3) Jumpstart our research initiative quickly and iteratively, so we could use some of the knowledge in our pilot designs and incorporate some of our questions in the pilot evaluation plan

I was able to achieve all of this, by bringing on one powerhouse Principal Designer and three badass interns (who had all been my students at General Assembly), and spreading my own (and my Principal Designer's) knowledge as far as possible by instituting pair design practices, rolling up my sleeves and whiteboarding with my team, participating in many rounds of iterative critique and pair design with each of them, and assuring that they all stayed motivated and understood what to do next to succeed. Even though at the end of all this, the company and I were not a good long term fit, I am extraordinarily proud of the ambitious young team that delivered everything on time, and helped the company land the Series C funding they sought.