Job description

Transform How Frontline Work Runs Enterprises struggle to manage hundreds of millions of dollars in frontline labor spend due to decades-old software and manual processes, creating massive, avoidable costs. Frontline labor often represents 40% of the P&L, yet the systems managing this $3 trillion market were built for static schedules and limited flexibility. ReadyOn was founded to reject that paradigm. Staffing is not a scheduling problem; it is a real-time supply–demand orchestration problem. ReadyOn is an AI-native labor operating system, built from the ground up for AI agents to perform real-time labor optimization—much like ridesharing platforms that match drivers and riders in real time, but applied to frontline labor instead of fixed, one-size-fits-all schedules. Who’s Building It AI is not a bolt-on feature in our platform. Every decision, from demand forecasting to shift assignment, flows through an adaptive, autonomous decision layer that learns from operational data and continuously optimizes for cost, compliance, and worker satisfaction. Behind that system is a founding team of experts in labor markets, enterprise software, and AI-enabled platforms: • Reza – Engineering leader who scaled enterprise systems at Google, Yahoo, and AT&T • Dominic – Operator who optimized labor-intensive operations in 21 countries • Mohammad – Stanford professor and leading expert in algorithmic market design ReadyOn has already proven product–market fit with multiple multi-million-dollar customers, consistent expansion within existing accounts, and measurable ROI that moves stock prices. About the role Managers today spend a significant part of their day overseeing highly repetitive and tedious tasks that prevent them from focusing on more crucial work. With the emergence of AI and agentic workflows, we're in a unique position to not just improve the status quo but redefine it. AI is central to ReadyOn's vision to transform how companies hire, schedule, and manage their workforce. We're looking for a Lead UX Designer to help shape the experience of our core platform and AI workflows. You'll embed within small, fast-moving pods where the goal is to ship high-quality work quickly and iteratively. This role has two equally important dimensions: reducing complexity and friction across existing platform experiences, and building and maintaining the component and design system foundation that enables the team to prototype and ship with speed. You'll work hand-in-hand with product and engineering to shape user experiences from 0 --> 1. This role is highly autonomous and hands-on, and requires someone who can hold the bar on craft, push back constructively when execution falls short, and move fast without sacrificing quality. You will report formally to our CTO/Co-Founder. What you’ll do • Drive end-to-end design quality across ReadyOn's core operator and worker experiences, from ambiguous problem definition through to hi-fi implementation • Prototype rapidly using AI-enabled and emerging tools, designing inside the product environment where needed • Evolve ReadyOn's design system, establishing component standards and AI interaction patterns that scale across the product • Partner closely with product and engineering to set and hold the bar on interaction quality, pushing back when execution falls short of the design intent • Co-lead user research interviews, usability testing, and synthesize insights to innovative designs • Consider all dimensions of an experience, including copy, flows, edge cases, and business context, and model this thoroughness for the broader team What we’re looking for • 6+ years of product design experience at a SaaS or B2B technology company; senior IC experience required • Deep UX expertise with a proven ability to work from requirements, run user research, and make principled design decisions under ambiguity • A portfolio demonstrating exceptional interaction design craft, including complex workflows, use of component systems, and polished visual execution • Willingness to work hands-on with emerging tools, including installing, configuring, and designing inside the software environment itself • Fluency in Figma, including component and design system work • Strong communication and the confidence to push back constructively when quality is at risk • A track record of owning design quality end-to-end, staying through implementation to get it right rather than handing off and moving on • Ability to work in-person with our team in downtown San Francisco Nice to have • Experience designing for agentic AI or automation-heavy workflows • Familiarity with designing for data-dense and complex platforms • Experience with workforce management, scheduling, or other operationally complex B2B products Location: Why In-Person Matters As a high-growth startup tackling complex, industry-defining challenges, in-person collaboration is essential to our success. Being together in our San Francisco office enables rapid decision-making, creative problem-solving, and strong team trust — critical in this formative phase. We work together in-office five days a week, with 25 remote days per year available on an honor system. You'll be part of building the culture, the technology, and the team from the ground up. Potential Recruitment Fraud Memo Recruiting at ReadyOn is handled directly by our in-house team or verified hiring partners. We will never request payment, bank details, or confidential personal information during our recruitment process. If you are contacted by someone claiming to represent ReadyOn and you are concerned about the legitimacy of the interaction, please contact us at careers@readyon.ai to verify any communication. Equal Opportunity Employer ReadyOn is committed to building a diverse and inclusive workplace. We are proud to be an Equal Opportunity Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. Equity & Benefits In addition to salary, this role includes comprehensive benefits, and may include bonuses & a meaningful equity stake in ReadyOn.

Requirements

Must-haves

Transform How Frontline Work Runs
Who’s Building It
Reza – Engineering leader who scaled enterprise systems at Google, Yahoo, and AT&T
Dominic – Operator who optimized labor-intensive operations in 21 countries
Mohammad – Stanford professor and leading expert in algorithmic market design
ReadyOn has already proven product–market fit with multiple multi-million-dollar customers, consistent expansion within existing accounts, and measurable ROI that moves stock prices.
What you’ll do
Drive end-to-end design quality across ReadyOn's core operator and worker experiences, from ambiguous problem definition through to hi-fi implementation
Prototype rapidly using AI-enabled and emerging tools, designing inside the product environment where needed
Evolve ReadyOn's design system, establishing component standards and AI interaction patterns that scale across the product
Partner closely with product and engineering to set and hold the bar on interaction quality, pushing back when execution falls short of the design intent
Co-lead user research interviews, usability testing, and synthesize insights to innovative designs
Consider all dimensions of an experience, including copy, flows, edge cases, and business context, and model this thoroughness for the broader team
What we’re looking for
6+ years of product design experience at a SaaS or B2B technology company; senior IC experience required
Deep UX expertise with a proven ability to work from requirements, run user research, and make principled design decisions under ambiguity
A portfolio demonstrating exceptional interaction design craft, including complex workflows, use of component systems, and polished visual execution
Willingness to work hands-on with emerging tools, including installing, configuring, and designing inside the software environment itself
Fluency in Figma, including component and design system work

Nice-to-haves

Experience designing for agentic AI or automation-heavy workflows
Familiarity with designing for data-dense and complex platforms
Experience with workforce management, scheduling, or other operationally complex B2B products
Location: Why In-Person Matters
Potential Recruitment Fraud Memo

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

aidesign systemfigma

Platform: gem
Effort: medium

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