Skye - Onboarding Redesign
Project Specs
At Skye, a four-sided marketplace for executive coaching, I worked as the lead designer to redesign the onboarding experience.
The goal of the new onboarding experience was to reduce friction while also giving it a modern visual refresh. As the sole designer, I drafted user flows, created wireframes and prototypes, and elevated the design system. I also gathered feedback from usability testing to further iterate on the design solution.
Role
UX Design
Visual Design
Usability Testing
Timeline
Jun - Jul 2022
Tools
Figma
Adobe Photoshop

Context
Who is Skye?
Skye is an executive coaching provider that works with HR leaders, coachees, and coaches. They provide coaching to over 700 leaders and have sold over $1.7M in gross marketplace and enterprise bookings within the first 3 years.
At Skye, the first step to meeting a coaching partner is to complete a matching process – the onboarding experience.
The Problem
Too long. Too much effort
What do the stats say?
The previous onboarding flow took 10 minutes to complete
60% of users fail to complete the onboarding process
Too many steps
There are seven steps to onboarding with multiple sub-tasks. This becomes tedious.
Recall over recognition
The questions ask leaders to write their goals without any prompting or examples. This can be difficult and time consuming for leaders who need help with self discovery.
Overwhelming information
The steps are text heavy and cramped. It’s easy to lose focus.
Personas
Who needs to find a coach?
The primary user group affected by this onboarding process are the coachees. These coachees, or leaders, are often Expert ICs, directors, VPs, c-suite executives, and emerging managers.
Field Research
Understanding best practices
I conducted a SWOT analysis of direct competitors to Skye, platforms our coachees frequently use such as LinkedIn, and platforms that have a more conversational approach like Duolingo. Key takeaways include:
Minimizing user input - we can reduce friction by leveraging questions that don’t rely on text input answers
Emphasizing the conversation - tone is key to stay engaged
Understanding relevance - coachees need to know what they’re doing is important to getting started
Minimalist and modern visuals - a clean UI helps keep focus and prevents overload

Goal
Simplify onboarding + visual refresh
We want to help the coachees determine their goals and find their coaching partner easily by:
Reducing the number of inputs
Engaging conversation
Providing clear and actionable steps
Ideation
Onboarding user flows
The algorithm for finding a coach at Skye leverages data on operational expertise (field, industry, experience level) and demographics (gender, ethnicity, life milestones).
I started by drafting task flows to experiment with the order in which questions were presented and worked with my PM and operations lead to pare down steps as much as possible.
Prototyping and usability testing
Design Exploration
Given the simplified flows, I started exploring how to present information and different data collection methods through rapid prototyping.
To validate these data collection methods, I conducted 5 usability tests using a greyscale prototype and asked questions like:
How did you find the experience of using this website to get matched with a coach?
Which approach for answering questions did you like the best? Why?
I noticed you went back to change the likert scales a couple times, can you tell me why?
Single-Click Buttons
Pros: Fast and straightforward, minimalist design
Cons: Doesn’t allow for much data collection
Text inputs
Pros: Enables the most detailed data collection
Cons: Requires the most effort from the user, very time consuming
Likert Scales
Pros: Most visually engaging, best for determining coaching preferences
Cons: Questions can add up quickly, too many options leads to choice paralysis and second guessing

Standardizing the design language
Design System
To help with visual interest and consistency, I defined a design system that also served as a foundation for many future design solutions.

Design Solution
A new and improved matching process

Single-click interactions
Most efficient data collection method that reduces platform friction
Context is key
Each question in the onboarding process should feel meaningful and know exactly where they are in the process
Minimalist Design
It is easier to guide focus and stay on task with a simple aesthetic
Outcomes
Success metrics
After rolling out the changes, we noticed positive changes in our user acquisition and client funnels such as:
70% decrease in onboarding time
50% increase in onboarding completion
40% net improvement in Skye’s B2C conversion rate
Reflections
Tailored systems
While optimizing the onboarding flow was a crucial part of this project, this project also allowed me to grapple with establishing a tailored design system for the first time. To even get started with the design system, I had to work closely with Skye’s CEO to understand the company values and mission. From there, I tried to emulate those values in the color and typography used.