WorkWhile is on a mission to help workers earn a better living and live better lives. While 80 million Americans face the instability of unpredictable hourly work, we are leveraging AI to create a flexible, efficient labor market where frontline workers finally have the upper hand. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, we are disrupting a $650 billion industry by putting people first.
The Role
As a Worker Success Specialist, you are the primary advocate for our community. You aren't just resolving tickets; you are building the trust that allows our marketplace to thrive. This role is perfect for a high-empathy, fast-moving problem solver who wants to navigate the "gray areas" of the gig economy and ensure every worker feels supported, heard, and empowered.
What You’ll Do
Empower the Community: Deliver world-class support via email, chat, and phone, turning complex worker inquiries into seamless success stories.
Guard the Marketplace: Proactively maintain platform integrity by managing Trust & Safety reports and ensuring all users adhere to our community standards.
Optimize the Worker Journey: Identify friction points in the worker experience and collaborate with Product and Ops teams to build long-term solutions.
Own the Knowledge: Create and update internal playbooks and external FAQs to help our worker community self-serve and succeed independently.
Drive Operational Excellence: Manage high-volume queues with speed and precision, ensuring our response times remain industry-leading.
Empathy-First: You have a genuine passion for the well-being of hourly workers and can communicate with clarity and warmth.
Critical Thinker: You don't just follow a script; you use data and intuition to solve the root cause of an issue.
Tech-Fluent: You are comfortable juggling multiple platforms (CRMs, Slack, Internal Admin tools) without missing a beat.
Adaptable & Resilient: You thrive in the ambiguity of a fast-growing startup and are comfortable with a flexible schedule to meet the needs of our workers.
Prior experience in Trust & Safety or Marketplace Operations.
Deep familiarity with the gig economy or hourly labor landscape.
Hands-on experience withIntercom or similar support ecosystems.
Skills Required
- Deliver support via email, chat, and phone
- Manage high-volume queues and maintain fast response times
- Experience using CRMs, Slack, and internal admin tools
- Strong empathy and clear, warm communication
- Critical thinking and problem-solving to address root causes
- Adaptable to ambiguity and comfortable with a flexible schedule
- Prior experience in Trust & Safety or Marketplace Operations
- Familiarity with the gig economy or hourly labor landscape
- Hands-on experience with Intercom or similar support ecosystems
What the Team is Saying
WorkWhile Compensation & Benefits Highlights
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Healthcare Strength — Healthcare is presented as strong for corporate roles with 100% employer-paid employee medical, dental, and vision premiums and generous family coverage. Platform workers also have free telehealth access and, for eligible W‑2 roles, an ICHRA allowance toward individual coverage.
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Leave & Time Off Breadth — Time off is broad for corporate employees with unlimited PTO and other leave provisions. Platform W‑2 workers also accrue paid sick time at one hour per 30 hours worked.
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Parental & Family Support — Parental leave is presented as generous for corporate staff, with 16 weeks for birthing parents and 12 weeks for non‑birthing parents. Family support also includes an onsite Mother’s Room.
WorkWhile Insights
What We Do
WorkWhile is an AI-powered next generation labor platform that helps businesses in light industrial, hospitality, and events achieve over 90% fill rates and reduce no-shows through AI and predictive machine learning. We ensure seamless shift execution with trained, on-demand workers supported by on-site leads, real-time performance monitoring, and a robust accountability system. Our worker-first model boosts retention through benefits like next-day pay, telehealth, and free upskilling, while our platform delivers real-time analytics and dedicated support for every client. By combining flexibility, reliability, and deep insights, WorkWhile helps businesses scale efficiently and stay competitive.
Why Work With Us
WorkWhile is a technology platform with product and engineering at its core. Founded by alumni from Google, Meta, Yahoo, and Airbnb, continuous innovation is our strategy. We are an AI-native company that doesn’t just adopt new technologies, we operationalize them at scale to solve real business challenges.
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WorkWhile Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy allows workers to work flexibly - either in person in one of our four hubs (San Francisco HQ, New York, Seattle, Toronto), or remote. We encourage employees coming in person to come 2-3x per week.
