Sentry

A 24-hour cross-disciplinary technology sprint aimed to develop a digital solution for a challenge presented by Microsoft.
Role:
UX/UI Designer

Duration:
August 2023, 24 hours

Responsibilities:
UX Research, Design Strategy, UI, Slide Deck

Tools:
Figma, Figjam, Grammarly
A cover image of a laptop showing the Sentry AI plugin

Overview

Situation/Problem

Within a team comprising Software Engineers and Data Scientists, I faced a 24-hour deadline to tackle a tech challenge presented by Microsoft.

Solution

A Microsoft e-mail plugin that allows users to detect and delete potential phishing e-mails sent by AI.
A person is working at a computer and an image of a Sentry E-mail plugin example is shown on the left

The client

A heavy hitter enters the fray

Since its establishment in 1975, Microsoft Corporation has played a pivotal role as a leading American multinational technology company in the computer industry.
Logo for Microsoft

4:00 PM - The Challenge

How might we transform data privacy settings and practices across multiple platforms, making them more appealing and secure for individuals?
An image of a clock counting down the time of 24 hours remaining

4:01 pm - forming the avengers

Great things are not done alone

I was assigned to a team comprised of 3 Software Engineers, 2 Data Scientists, and 1 UX Designer (me!). Initially, we struggled to be on the same page and decide on a direction. It was a struggle.

In the end, we were able to put aside our differences and work towards a common goal. I suggested we take some time to explore the problem space before committing to anything first.
An image of a team of engineers, data scientists, and ux designers

4:30 pm - Planning

Exploring the problem space

We explored the problem space by doing independent research, bringing back ideas, and doing a group vote to decide the direction we wanted to go. Our choice was AI-powered phishing / Social Engineering.
An image of the team doing research and voting

6:00 pm - Narrowing it down

Using Data Science for the win

Although we struggled at first, we got back together and tried to assign each other roles. I tasked the data scientists to come back with some more secondary research.
An image of two crossing swords
1.7 Billion phishing attacks per year
An image of money
$2.7 Billion USD lost to phishing e-mails
Logo of chatGPT
ChatGPT is being leveraged by scammers
An image of a clock counting down the time of 21 hours remaining

7:01 pm - User interviews

Asking the people who matter most

With such little time, I still made it a priority to talk to users who were affected by the problem space. I called three people who fit the criteria of people working at tech companies. Through listening to their answers, I was able to refine the problem space and create a new HMW statement.
An image of three men in their middle thirties being interviewed

8:00 pm - User Persona

Meet John Banks: A victim of AI phishing scams

Through the user interviews, I better understood the problem by asking real people. I called three people who fit the criteria of people 25 and up, currently working in tech, and familiarity with Microsoft. From there, I crafted a basic persona from the data I got from the interviews and presented it to the team.
An image of John Banks, a 30-something male

8:30 pm - Reframing the Problem Space

Focusing on the problem with a new HMW

With such little time, I still made it a priority to talk to users who were affected by the problem space. I called three people who fit the criteria of people working at tech companies. Through listening to their answers, I was able to refine the problem space and create a new HMW statement.
How might we help employees working in tech decrease the risk of phishing attacks to prevent their company from losing money to these attacks?
A countdown timer saying there is 19 hours and 15 minutes left

8:46 pm - Taskflow

A taskflow fit for everyone

Finally, armed with a taskflow and a persona, my teammates could fully grasp the concept I was designing. The software engineers were also grateful that I kept mindful of their capabilities and was willing to share ideas.
An image of a task flow

9:15 pm - ITERATIONS

Going from lo-fi to hi-fi

I made sketches using good old pen and paper. I used Figma to make high-fidelity versions once everyone was on board with the sketches. I did a little bit of user testing with the team as much as I could, but was limited due to time constraints.
An image of different sketches for Sentry
⬇️
An image of different wireframes that was translated from the previous wireframes

1:00 am - please let me sleep. Not yet? okay.

Securing a smooth hand-off

I finished a little bit before 1:00am and made sure to stay on another two hours to help ensure a smooth transition. As I was waiting, I started creating a logo and started the slide deck. At around 3:00am, I took a quick nap and woke up in the morning to finalize everything before the deadline.
Picture taken for PuppyHero – https://puppyhero.comby BRUNO CERVERA
A countdown timer saying there is 13 hours

3:00 pm - finishing before the deadline

Stay secure using Sentry

After a long night, we were able to build our concept to be an e-mail-based solution add-on branded as "Sentry". It would detect AI phishing and thus create a more secure environment for Microsoft users.
Logo of Sentry
Harley working in the Studio Republic office, Winchesterby Studio Republic

Features

We decided on an e-mail-based solution add-on called "Sentry" to detect AI phishing and thus create a more secure environment for Microsoft users.

The plugin would detect AI phishing scams and give users options for handling them.

  • Detects potential phishing scams and AI usage in communications
  • Protects customer information

  • Maintains communication integrity for individuals and enterprises
A countdown timer saying there are 0 hours left
An image of two laptops

Hi-Fi Demo

The final unveiling

We made it. It was time to present our solution proudly to the judges. We were all proud of what we could accomplish in such a short amount of time.

Video Demo

Solution Impact

What we hope to achieve

  • Reduce phishing click-through
  • Reduce Data Breaches
  • Improve user & employee trust in platform

Next Steps

  • Implementing as automated email plugin

  • User Testing & Revisions

  • Summary statistics for each users’ account
man using laptop beside woman holding penby Jason Goodman

Takeaways

What I learned

💬 Communication is key amongst team members. It is very easy to breakdown in communication, so it's important to keep the communication going smoothly.

🧠 Same problem, different mindset. We come from different areas of expertise, but we all have the same goal of solving the same problem.

⌚ Staying on track. Managing tight deadlines can be difficult especially this scenario of only 24 hours.

Thank you! 🙏

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