Paradox

Paradox is a conversational recruiting platform built around Olivia, an AI assistant that handles the repetitive communication load of hiring: screening candidates, answering FAQs, scheduling interviews and guiding onboarding paperwork through natural conversations on SMS, WhatsApp, web chat and email. It was founded in 2016 in Scottsdale, Arizona by Aaron Matos, and it specializes in high-volume frontline hiring across retail, restaurants, healthcare and logistics.

The company raised a $200 million Series C in December 2021 at roughly a $1.5 billion valuation, backed by Stripes, Sapphire Ventures and Thoma Bravo. In October 2025 Workday acquired Paradox for about $1 billion, folding Olivia into the Workday ecosystem. Published case results include Flynn Group automating 90 percent of hiring steps and 7-Eleven saving a reported 40,000 store hours per week.

Olivia works in more than 100 languages and the platform tracks over a thousand hiring metrics. Reviewers note the chatbot can struggle with complex or nuanced queries, and the post-acquisition roadmap is now tied to Workday's suite. For employers hiring hundreds or thousands of frontline workers a year, the combination of conversational apply, automated screening and end-to-end scheduling is the core appeal.

1. Engage Paradox (now via Workday) for an enterprise demo.
2. Define screening questions, scheduling rules and hiring-event workflows.
3. Connect your ATS (Workday, SAP SuccessFactors and others) for real-time sync.
4. Deploy Olivia on your career site, SMS, WhatsApp and email channels.
5. Monitor funnel metrics like time-to-apply and time-to-hire, then tune conversations.