Designing Secure Job Application Widgets for Grayscale's AI Chatbot

FIX

Context

Grayscale is a B2B hiring platform that integrates with customers’ ATS to automate high-volume recruiting tasks. At its heart lives an AI Assistant named Gracie.

As the sole UX Designer, I partnered with the PM, VP of Product/Engineering, CTO, and developers to translate Gracie's rapidly-evolving capabilities into human-friendly, scalable interfaces.

High-Level Challenge

Gracie was mainly an embedded chatbot on customers’ career sites, helping candidates identify which jobs they were qualified for. As she expanded to guide applicants through the full application process, I ensured each new capability worked smoothly across chat and mobile experiences.

1. Resume Uploads

Candidates couldn't upload their resume directly into Gracie's chat window. They had to follow a link to the job application, which broke the conversational flow.

2. Demographic Questionnaires

In order for Gracie to maintain compliance as a job application, an EEOC questionnaire needed to appear at some point during the chat experience.

3. Platform Parity

Many candidates interact with Gracie via SMS and WhatsApp channels, so both these experienced needed to be delivered consistently across desktop and mobile web.

FIX

With no established UX norms for AI jobseeking, this design space was quite open.

Discovery

Without direct access to candidates using Gracie, I turned to secondary research: job-hunting forums, candidate discussions, and competitive analysis for a window into how job seekers perceived AI in the application process.

Many candidates interacting with Gracie were applying to frontline roles where English fluency is not a requirement. This led me to consider how many marginalized folks may be applying through Gracie, and does this experience make them feel comfortable? After all, it’s well-documented that applicants sometimes alter their names on résumés to appear “less foreign.”

I worried that if Gracie’s flow didn't feel transparent or legitimate enough, candidates might assume she was just another biased gatekeeper and abandon their applications altogether.

FIX

Interestingly, this take is not unusual on Reddit. If even the self-proclaimed “peak privelleged” don't trust EEOC questionnaires, that’s further evidence that this is a UX problem!

Findings

Few Established Patterns

AI chat–driven applications are novel and lack established UX norms.

Usability Issue

Old Computers

Gracie only supported .PDF and .DOCX uploads, which could exclude candidates who are not computer-savvy or running very old versions of Windows.

Tech Accessibility Issue

Linkouts Interrupt Flow

Opening surveys in pop-ups or tabs causes confusion and drop-off.

Usability Issue

Literacy Barriers

Candidates with limited English proficiency or lower digital literacy often apply to frontline roles. Even with clear UX, this process may feel intimidating or inaccessible.

Bias Issue

Density & Formality of EEOC Content

Dense EEOC jargon might feel overly formal and spook candidates at the end of their applications.

Trust Issue

Access to a Personal Computer

Pop-ups often blocked on public computers, making this process exclusionary to applicants who may not own their own computer.

Tech Accessibility Issue

Mobile-First Experience

Most frontline workers are applying from their phones. Small screens amplify pain points like jargon density, modal pop-ups, and non-mobile-friendly flows.

Tech Accessibility Issue

Fear of Discrimination

Candidates of all backgrounds fear their answers to demographic data questions will affect hiring outcomes.

Bias Issue

Solution

  • Stepped Form: Rather than overwhelming candidates with a wall of dense legal text, the survey followed a stepper format. Each step contained only one or two questions, keeping the interaction lightweight and providing a sense of progress.

  • Signals of Trust: Before opening the survey, Gracie reassured candidates in plain language that responses were voluntary and had no impact on hiring outcomes. Inside the flow, an official EEOC disclaimer and shield icon reinforced privacy and compliance. Informational copy linked out to EEOC documentation for candidates who wanted more detail.

  • Tone Shift for Security Once the EEOC widget opened, Gracie’s conversational voice paused and shifted to a more formal, secure tone. This contrast underscored that demographic answers were confidential and treated differently than general chatbot interactions.

Impact

My design allowed candidates to complete EEOC surveys securely across all channels, while preserving conversational flow and strengthening trust in Gracie. This work helped Grayscale to maintain compliance at a massive scale, and contributed to improved completion rates.