One project I'd like to talk about is my work on designing what we would call "Suggested Items".
When I joined FareHarbor, one thing that our platform didn't offer yet, but many potential customers told us they wanted, was the idea of a Shopping Cart. Prior, for simplicity the company had made due with a booking flow that led directly to a payment form to great success, but as we continued to expand, the need for a proper Cart and the other benefits we'd get with developing one became apparent.
In the early stages, I also helped put together the early concepts of our Cart via Sketch prototypes to map the user flow, as well as to act as a Marketing piece for our Sales team at a large conference. We hear this won over many of our new clients who were stubborn about holding off on on-boarding with us until we had Cart :)
You can find the Interactive Prototype here: https://invis.io/BH9J88MC9
Ideation
While conceptualization for restructuring our data model to include the idea of an Order layer to support Cart was underway, we started thinking about the idea for "Suggested Items"; the ability to upsell, or suggest other activities. Ultimately, this was the main reasons users wanted a Cart in the first place, to allow them to sell packaged activities, such as a Parasail and Jet Ski activity package, or round trips for companies such as ferry operators.

Quick notes to start to wrap my head around what data we needed and how it should be organized.

Design
We came to the conclusion that the data model should support a couple things.
1. We need to allow a way to group items together
2. Users would then be able to select an item group to use as suggested items for per item
By creating these groups, this allowed the most flexibility and scalability for creating company dashboard setups with a lot of repetition. Creating "Item Groups" satisfied our needs for allowing users to suggest items, and also paved the way for more features that we had on our roadmap including the ability to define a conversion funnel by breaking down item selection into larger groups, ie. a funnel that looks like this:
Location > Type of Activity > Activity Item

My initial explorations included an organization for how to setup funnels in the future, but we pulled back the design for the initial  feature release.

I worked closely with one engineer to make sure that the data model made sense and was feasible for what we were trying to accomplish. In-order to achieve what I described above, we settled on a many to many relationship structure.
I provided the high fidelity storyboard mocks to pitch to the directors as well as hand off to the engineer to develop the backend. Once we got the data model in place I jumped in to refine the front end styles and copy where needed.

The many screens and iterations I worked through spanning from company dashboard settings to end user booking views in Sketch before handing off final prototypes. 

One setting we included to allow rolling this out quickly and easily was the ability to setup a default set of suggested items that would display on any item their customer books, with overrides being set per item if need be.

Setup page for setting default suggested items

Also note that we have different setups for the Cart and the Confirmation page. This was because the conversion goal and user intent varied between both views, so that the message should be modified to be more relevant, i.e. on the Cart view, the company may want to suggest a package item, but once the user has completed their purchase, the company may just want to promote seasonal deals or popular activities.

High fidelity mockup of what the end user sees in their cart.

The trick with upselling is getting the most relevant items in front of the customer at the right time. With this feature in addition with the Cart launch, companies were finally able to allow easy roundtrip and package bookings to their customers. This is a win for companies as they saw an uptick in revenue per order, and a win for customers as they could more easily book multiple activities at one time while they plan their trip.
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