In 2018, it was time to update Pipedrive's meeting scheduling tool. There were many issues with the version that was live at the time, the most prevalent being that it allowed for double bookings, but there were also other usability issues and the fact that it didn't fit into our users' workflows. We found ourselves at Pipedrive using competitors' tools to schedule sales calls and user interviews. This was a clear opportunity for us to make salespeople truly efficient.
For research, we:
▪ looked into user feedback for the existing functionality;
▪ looked into usage data of the existing functionality;
▪ conducted 10 interviews with customers;
▪ conducted a survey;
▪ of course, looked at what's been written on the topic and what the market offers. 
We had lots of hypotheses about what users wanted from the feature, so we wrote them out, mapped them to the different research methods, and made sure to find out if the hypotheses were true or not.
Without wanting to share specific percentages from proprietary research, I feel I can share the following findings from our survey:
▪ a large percentage of our users said that the back-and-forth with their customers makes finding meeting times complicated;
▪ a large percentage of users sometimes or often need 3 or more interactions with their customers to get meetings scheduled
▪ almost every second customer said that it sometimes takes 3 or more days to get a meeting time agreed upon;
▪ almost 2/3 of our customers needed to book meetings at least once per day.
When defining the functionality, we set a goal for the new Scheduler to be better aligned with our users' workflows, and to seamlessly integrate with their calendars so that double bookings wouldn't be a possibility. From the design side, we insisted on a mindset shift in terms of "Where do we put this feature?" to "When and where do we have an opportunity to help users?".
We focused mostly on the Calendly style "sharing my availability" function, where users would set their bookable hours for meetings, define the length of the meeting and some constraints around it and then lets the system allow customers to book meetings at whatever free times there are in their calendar within the defined hours. However, our founders – very busy men, but still very much hands-on with product development at that time – insisted that we also offered the functionality to select a handful of meeting slots manually and send these out case-by-case. We looked into that and did find use cases, for example when a user has a busy schedule but is willing to override some existing meetings to meet their customer – a more personal touch if you will. So our new tool was set to be a two-headed snake.
Based on user interviews, we defined key user stories and ordered these according to how many times they were mentioned. We ran a MoSCoW prioritization on functionality. We then created at least 7 raw concepts for the feature with my co-designer on the project. We synced up and weighed the pros and cons of each, then iterated further on some winning ones, kind of competing with one another. The size of our organization at the time, and the way the office was set up, allowed us to do lots of ad-hoc guerilla testing with colleagues which proved extremely useful for rapid feedback and iteration. It was an intense and fun process, but I must say that the competition bit felt a bit uncomfortable.
We aimed for:
▪ an increased number of future events scheduled per Pipedrive user;
▪ decreased time to schedule an event (a happier, easier path to a scheduled event);
▪ increased retention for the feature.
The end product
Here's Pipedrive's official demo video for Scheduler:

Scheduler demo

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