Onboarding Made Easier


Smartsheet, a cloud-based project management solution, wanted to increase conversion rates from trial to paid subscriptions. To solve this problem, we designed a new user-guided onboarding process. The result gave Smartsheet's users an improved end-to-end emotional experience and motivation to learn more, particularly at the end of the trial period, which is the most critical time for increasing conversion.

My Role: Interaction Design, Prototyping, Usability Testing

Tools: Axure, whiteboarding, pen and paper

Duration: 2.5 weeks

Team Size: 3


The Opportunity

Smartsheet is a Software as a Service (Saas) that provides an interactive spreadsheet with a robust set of interactions to help teams collaborate and get projects done efficiently.

They approached us to bring new life to their onboarding process. They had tried several methods with varying results, and needed a fresh take on the design. They asked us to focus specifically on a new onboarding process that would help increase conversion rates for new users who arrived at their website through PPC ads for "project management software." 

Their detailed research showed that a user's mastery of three key features was most likely to lead them to upgrading to a paid account at the end of their free trial:

  • Row hierarchy - knowing how to indent and outdent rows to nest tasks in the sheet
  • Column properties - knowing how to change the column type and title by double-clicking
  • Sharing - knowing to click the Sharing button at the bottom of the sheet to collaborate with colleagues


Stakeholder Interviews

The research phase of this project began with stakeholder interviews. Before we met with them, we wanted a clear picture of what we would ask and what information we wanted to focus our attention on to best solve their problem. We came up with a diagram that helped us develop our questions and outline our strategy.

Usability Testing

After we met with our stakeholders and were clear on their goals, we decided the best course of action would be to conduct usability tests on the product as it is existed. The clients wanted something to enhance the current product and the best way to learn how users felt about it was to ask them.

The team conducted usability tests with five participants with an average of five years of project management experience. All participants had used MS Excel in the past and other project management software, but were completely new to Smartsheet.

They were observed as they signed up for the first time and went through Smartsheet's tutorial, which consisted of a video and a screen filled with 4-7 tips using a Smartsheet-provided template. Participants were also tested on a blank sheet to see if they retained the information they learned.

Affinity Diagram

After collecting the data from the tests, the team made an affinity diagram to capture user data and feelings about the product.

Our affinity diagram reinforced our key objectives:

  • Present tips and tutorials in more timely and less obtrusive ways
  • Increate discoverability and learnability of key features
  • Redesign toolbar to align with user’s mental model
  • Give users “quick wins” to keep them motivated
  • Build personality into the design to appeal to the users at an emotional level


Using this information, we developed our persona, Shane, who we would use to guide the rest of our design process.

Journey Map

The journey map below is a visual representation of Shane's experience going through Smartsheet's tutorial. Though he experiences some early wins, by the end he's feeling unsure that Smartsheet is right for him.



User Flows

Having collected our user data, the team created a user flow to represent Smartsheet's current model.

Design Studio

We then set a plan for how our tutorial would be different from Smartsheet's current tutorial. We would begin by conducting four design studios. The first would be focused on a brand new welcome screen that would appeal to the user's emotions. The second would focus on designing the meat of our project - improved tooltips for teaching users to use Smartsheet, piquing their interest and launching them into using the product.

The last two design studios would address tweaks to the UI that our usability tests showed would help users: the toolbar and the template selection menu. Decreasing cognitive load and increasing discoverability in each of these areas would only motivate users more to find out what Smartsheet has to offer and increase the opportunity for conversion.



All three team members sketched different versions of the welcome screen, tooltips, toolbar and template menu, then presented their versions to the other team members. As a group, we selected the best features from each sketch to be developed in our prototype.

The tooltips would look like conversation boxes and give the user succinct tasks to complete one-by-one. As a task was completed, a new task would pop up letting them know what to do next and showing them their progress. This addressed our usability test findings that many tips popping up on the screen was overwhelming users.




The toolbar would be less crowded and organized under headings for maximum learnability and decreased cognitive load. Buttons would be grouped using more negative space around them created by removing two buttons that users didn't employ to complete their tasks. A new Gantt chart icon that looked less indented and more like a chart would be tested. Data showed that users had a hard time distinguishing the Gantt chart view button from the button that indented rows, one of the key features tied to increasing conversion.




The template menu would be simplified. Templates were a big hit among users, but the sheer variety of them was hidden behind a drop-down menu. We pulled the categories out and put them front-and-center. We also uncluttered the selection screen to let them shine.




With our final sketches created, the group divided the work of building our prototype. I was in charge of creating the tooltips and developing the interactions the users would have with them.

Our redesigned onboarding process shows users how to use Smartsheet using data from their own project to get them up and running and emotionally connected to the product from the start. The messaging assures users that the tutorial will be quick to go through (because we know their time is valuable). When complete, users can decide to continue working or start a new sheet.



We conducted seven usability tests on two different versions of the prototype. These tests were done in exactly the same format as our tests with the current product in the research phase of the project.

Our users had an average of five years of project management experience. They were familiar with MS Excel and other project management software, but completely new to Smartsheet.

After our first round of usability tests we created an affinity diagram to sort our data and devise the best iterations to our design that would make the most impact to the user's overall experience.

  • Users thought our tutorial was easy to use in general. There was some confusion about exactly where the tooltip was pointing, so we added red boxes and light yellow highlights were applicable to focus their attention. In our second round of testing, this was no longer an issue.
  • Users retained information. When asked to recall what they just learned using a blank sheet, all users tested were able to complete the tasks with no problems.
  • Some users felt the tutorial was too simple. They didn't see the value in the product or how it differed from project management software they already had. This could be remedied by expanding the number of tutorials and giving the user an option to do beginner or advanced levels.
  • Overall, users wanted to learn more about the product. The majority said they would continue editing the sheet they started during the tutorial, and would come back to Smartsheet to do more work on it. They were excited to learn more.

Based on this data, we created a new journey map to show our persona's journey based on our redesigned prototype. High emotional satisfaction at the end of trial period, shows that a higher conversion is likely.

We presented our findings and design solution to the client, and proposed these next steps:

  • Implement tutorial on live website.
  • A/B testing with real customers.
  • Validate solution by tracking conversion rate.