All Episodes

September 19, 2025 56 mins
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/ Stop wasting money on lead-gen tools that don’t work. Learn how top recruiters are winning on LinkedIn with content, messaging, and automation—without spamming.  Get live coaching, ongoing support, and a proven system to drive revenue inside Digital Recruiter Bootcamp. Join now: DigitalRecruiter.io/bootcamp

Get the best and most current digital recruiting insights, tips, and strategies every Sunday—straight to your inbox, for free: https://www.digitalrecruiter.io/drnewsletter

For more information about Digital Recruiter, click HERE ---> https://linktr.ee/thedigitalrecruiter

 

Mark as Played

Advertise With Us

Popular Podcasts

My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.