Episode Summary

When Jessica Oliver left her full-time job in late 2023, she didn’t just go out on her own, she reinvented her entire career. In less than a year, Jessica has launched an agency, built an AI-driven GovCon platform, and become a standout voice in the recruiting space through strategic content and intentional outreach.

This episode is a crash course in how to build a solo recruiting business that actually scales.



Jessica shares how years of agency and in-house recruiting led to disillusionment with corporate America, what finally pushed her to bet on herself, and the mental rewiring it took to go from salaried recruiter to entrepreneur. From the mindset work that keeps her grounded to the tech tools she stopped overcomplicating, she breaks down what worked, what didn’t, and what helped her stand out in a noisy market.

We also dig deep into Jessica’s discovery of the GovCon world, how a coffee meeting turned into a seed investment, and how she leveraged her recruiting background to build Clara, an AI-powered federal procurement tool. Whether you’re new to recruiting or thinking about your next business leap, this episode is a masterclass in action, alignment, and building what you wish existed.

 

Jessica's Bio

Jessica Oliver is a veteran tech recruiter turned entrepreneur and innovator in the GovCon space. After 15 years in both agency and in-house roles, including a stint recruiting full desk at Disney, she launched her own agency and quickly followed with Clara, an AI-powered federal procurement platform. She's passionate about ethical recruiting, modern sourcing, and building real relationships in an AI-saturated market. Jessica is also a proud mom of three, an advocate for veteran-owned business, and a rising voice in the Digital Recruiter community.



Connect with Jessica on LinkedIn at https://www.linkedin.com/in/jessicaolivertechconnect/ or at https://www.olivertechconnect.com/



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