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Legacy Strategies

Redesiging the Website Experience


Legacy Strategies is a start-up with an evolving business model. They launched as a marketing agency working with businesses seeking creative services, however, they saw an opportunity to cultivate a network of creative freelancers as well. They have now evolved to a staffing agency model where they offer not only creative services to businesses but also help freelancers find opportunities.


As their business model evolved, Legacy Strategies realized their website should too. They aim to seamlessly connect businesses with creative services and freelancers to project opportunities with a human-centered approach.

Role and Team

My Role: Project Manager and UX Designer with focus in research, synthesis, product development, and usability testing.

Team Members: Sari Beall, Jinnah Choi, Jeo Tovar, and Me!


3 Week Sprint


Google Suite



Client Kick-Off Meeting

We learned that Legacy Strategies’ business model is more than it currently seems. From the original site, it was unclear on all of the services they offer and what values they uphold as a respected creative solutions service. They informed us that they used to only offer marketing solutions for businesses, but that they have recently pivoted to becoming a creative hub for freelancers and businesses to come together and work on projects -- and that process was not yet clear.

Research Strategy

We dove into our discovery phase by first identifying our assumptions and searching for insights via contextual inquiries, surveys, user interviews, and running analyses on the competition. We also understood that we would need to gather data through the lens of two audiences.

2 Target Audiences

businesses seeking creative services, mainly gen x

Freelancers and Creative Professionals


About the current website

  • Users are confused as to what services are provided
  • Users are unaware about the values important to Legacy Strategies
  • Users want more transparency in regard to the process they can expect to encounter

About the services provided

  • Price is a deciding factor when it comes to choosing a staffing agency, but users also want to work with a company that ‘puts people first’
  • Businesses want to see portfolios and resumes of freelancers
  • Businesses and freelancers want to foster a relationship for future opportunities
  • Freelancers will select projects based on personal interests
  • Freelancers want to keep learning and evolving their skillset

Original Website and Contextual Inquiries

Our assumptions were validated about the current website through 4 contextual inquiries in which we asked users to walk us through the original website.

Users wanted more clarity around the services offered and processes they would encounter when working with Legacy Strategies. Additionally, they wanted to see the values illuminated throughout the site as it was so foundational to the company.

Surveys and User Interviews

Surveys were sent out to obtain quantitative data like demographics, how often users were working with staffing agencies, and usage of social media platforms as a tool to market and connect. We received about 25 survey responses.

8 user interviews were conducted to understand the motivations, behaviors, goals, and challenges of businesses and freelancers, whether their search was independent or through a staffing agency.

Businesses seeking creative services

  • Understanding why they are seeking creative services
  • Why they choose one service over another
  • What their current experience is like
  • What pain points they encounter
  • What they value most in booking these types of services
  • What type of relationship they prefer or expect have with freelancers or with a staffing agency

Freelancers seeking opportunities

  • How and why they choose the opportunities they do
  • What experience they expect to have when working independently or with a staffing agency
  • What they value most about being a freelancer
  • What type of relationship they prefer or expect to have with clients or with a staffing agency
  • Learning about their habits when it comes to their own professional development

What Businesses were saying:

“I want someone that is experienced and that I trust to get the job done.”

"My challenges usually center around experience and financial constraints."

"I look for experience, expertise, creativity and professionalism when hiring a freelancer."

Of businesses never hire a freelancer through a staffing agency

What Freelancers were saying:

“I find it frustrating when people don’t understand the process and undervalue me.”

It's important for me to understand the clients goals and what they want to achieve."

"People want a lot from freelancers but don't want to pay a fair price."

Of freelancers never use a staffing agency to find opportunities

Additionally, we took a look at competitors to understand their offerings.

See Competitive Analysis


Synthesis & Insights

After affinity mapping our data, we learned that businesses and freelancers had various considerations before making a decision. Businesses were driven by 4 points when making a decision and freelancers were motivated by 5 factors when selecting opportunities.

Businesses hiring Freelancers

Businesses want someone who’s professional, meaning someone who will communicate, take direction, and understand their vision.

Finding someone who aligns with their personal values is highly important. Businesses want to work with someone with integrity and someone they can trust to get the job done.

Businesses want assurance that they’ll be working with a skilled and professional freelancer.

Businesses have constraints they need to consider as well. Availability, budget, and the process itself can be challenging.

freelancers Seeking Opportunities

Freelancers are driven by their personal goals and value clients that "put people first" and have a more holistic approach to their business.

Maintaining a professional relationship is just as important to the freelancer as it is to the business as both parties are invested in the project and want a successful outcome. Freelancers value the client’s needs and want to understand their story in order to help them achieve their goals.

Freelancers across the board, have similar frustrations of feeling undervalued and dealing with clients who don’t want to pay a fair price for services and have unrealistic expectations. To circumvent these frustrations, freelancers will set up a working agreement.

Freelancers take it upon themselves to keep learning and applying new skills. Cost and time are two constraints that freelancers face.

Freelancers value building a community as it oftentimes leads to opportunities, plus they receive support through their network. Freelancers also aim to have a strong online presence, through social media and/or an online portfolio.

Identifying Our Users & The Problem

Let me introduce you to Jet, the business owner, and April, the freelancer. They are the amalgamation of our research and led us to uncover the main problem statements.

Jet, The Coffee Connoisseur

Jet runs a small coffee shop in downtown Chicago. He is reopening after being closed for so long due to covid. He wants to rebrand and revitalize his social media platforms to attract new customers.


  • Find a freelancer that is experienced and will understand his mission
  • Find a freelancer that is in his budget, but will execute the scope of work
  • Wants to be hands-off on details, but kept in the loop

pain points

  • Not tech-savvy
  • Doesn't understand the freelancer's workflow
  • Services can be expensive


  • Prefers direct methods of communication
  • Wants to outsource work that he doesn't have time to learn or execute

April, The Dream-Maker

April is a brand strategist that is looking for a contract gig that she is passionate about. She wants to work with a client that understands her process and is respectful of her work. She enjoys working directly with the client so she can understand their mission and bring their vision to life.


  • Getting compensated fairly
  • Adding work to her portfolio
  • Learning new skills

pain points

  • Feeling undervalued
  • Feeling the need to over-deliver to satisfy clients
  • Overwhelming competition


  • Creativity
  • Relevance
  • Recognition

Identifying the Problem

So, how might we...

Jet is busy running his coffee shop and needs to hire a specialist to rebrand his business because he is not the most tech-savvy person and he would feel more comfortable hiring a creative professional that he could trust.

...help Jet connect to freelancers that are creative, professional, and align with his values?

April wants to distinguish herself as a creative freelancer so that she may work on projects she’s passionate about to evolve her skill set and create long-lasting connections.

…bridge the gap between April and the client so there is more trust and transparency in the process?

Understanding the Lines of Interaction

It was important for Legacy Strategies to be meeting with both business and freelancer before establishing a working agreement between the two parties. They wanted to be hands-on to be able to properly vet businesses and freelancers so they could continue providing quality services and add that 'human' touch to their business model.


Legacy Strategies' Pillars

As we held design studios with multiple people, including the stakeholders at Legacy Strategies, we wanted to ensure the pillars on which their business stands on were intertwined in our features.

These 5 pillars were identified in our client kick-off meeting and these themes kept reemerging throughout our research.

Feature Set

Our list of ideas was narrowed down to the following features. These were the most important features to prioritize based on our research and time constraints.

Outlining the process
Freelancers want clients to understand their process. Businesses want transparency and want to know ‘what they are paying for.’ Both parties want to understand the process of working with Legacy Strategies.

Form submission around empathy
In addition to Legacy Strategies standing on a pillar of empathy, businesses want to work with freelancers with integrity and freelancers value clients that put people first.

Portal with a checklist of goals and deliverables
Building trust through communication and transparency is highly important for both parties. It is a way for both parties to stay organized and accountable.

Freelancer profile
Businesses want freelancers that are vetted and recommended. They want to know that they are working with an experienced and creative individual.

Project listings
Freelancers want to be able to select work that aligns with their passions and needs.

Designing the Experience

With our features narrowed down, we shared ideas on how we could bring them to life as we sketched out quick wires through a session of crazy 8's. Building out task flows helped us visualize our users' journey.

For the purpose of this case study, I will be focusing on the form submission around empathy.

Business Task Flow

Because empathy was a strong theme that emerged throughout our research and is a main pillar for Legacy Strategies, we introduced a questionnaire during the onboarding process that would inquire about values and past experiences businesses had with freelancers.

Businesses would also be able to view recommended freelancers based on their project needs and "empathy questionnaire" after creating an account.

Freelancer Task flow

Similarly, freelancers would also fill out the "empathy questionnaire" during onboarding. After creating an account, freelancers would be able to browse project listings based on their needs.

Testing & Validation

Design. Test. Iterate. Repeat.

For the purpose of this case study, I will be focusing on the form submission around empathy.  During the onboarding process, this form submission would inquire about values and past experiences businesses had with freelancers.

We were excited to introduce this feature to our testers. To our surprise, users were NOT 100% sold on this idea.

Round 1 of Testing - Lo-Fi

Round 2 of Testing - Mid-Fi

Final Hi-Fi Wireframe

Users liked the idea of the "empathy questionnaire," but found it overwhelming and questioned the importance.

They did think the emoji's were an interesting way to answer questions.

Users enjoyed the 'cards' in which they could select the values that resonated with them.

We decided to move the 'cards' up since users were delighted by this part.

Users wanted to know why values were important and how they related to their project/work.

We decided to make the "empathy questionnaire" optional this time around (users had the option of filling these out at a later time).

But still, users wanted to know what is it that Legacy Strategies wanted to learn and why was this important, especially if the responses were not required.

Again, we were challenged on how to reduce the cognitive load and streamline this page.

We decided tweaked the question asked with the cards from "what values resonate with you" to "which values would you want to see reflected in a working relationship."

By doing this, we hope to draw the connection as to why we want to collect this information and how it will be used.

We overhauled the remainder of the questions so they could easily be answered through emoji's.

By doing this, we hope to eliminate the previous hesitation around this section.

We learned a lot about how to refine our prototype during testing. Take a closer look at some of our other results!

View Usability Test Results

"Aha" Moment

We hit an 'aha' moment when our research showed that 66% of businesses and 68% of freelancers did not use staffing agencies for a multitude of reasons. Both parties had negative feelings towards staffing agencies. Businesses felt that staffing agencies are expensive and the process of working with them can be cumbersome. Freelancers felt that there is too much competition and they are not matched with positions that suit them.

We suggested that Legacy Strategies rebrand as an 'All-In-One Creative Hub,' even though on the backend they would function as a staffing agency. We felt strongly that rebranding would portray them as a welcoming and trustworthy company passionate about connecting people through their desired needs.

The moment we've been waiting for...
the hi-fi prototype!

Congrats, you made it to the end! Treat yourself to a happy dance!

We were pleased that the client was beyond thrilled with our final prototype. We look forward to staying in touch to see how the recommendations are implemented and the results from those implementations.

Additionally, I encouraged some team members to take the lead during client meetings as they are naturally more reserved. I am proud of their growth and willingness to step outside their comfort zone. I find it important to support others in spaces that they might not feel 100% confident because, at the end, we only grow by the things we are challenged by.

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