Jessica Oliver

CEO

Orlando, Florida, United States15 yrs 2 mos experience
AI Enabled

Key Highlights

  • Built a successful automated recruiting agency from scratch.
  • Led AI adoption in talent acquisition at Fractal.
  • Scaled teams rapidly during hypergrowth phases.
Stackforce AI infers this person is a Recruitment Technology expert with a strong focus on AI-driven talent acquisition.

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Skills

Core Skills

RecruitingAi Implementation

Other Skills

Automated recruiting systemAI analysisPersonalized outreachSubscription-based modelTeam scalingTalent acquisitionArtificial Intelligence (AI)HiringStaffing ServicesProject ManagementProgram ManagementChange ManagementTechnical RecruitingContract RecruitmentGrowth Strategies

About

My career makes a lot more sense in retrospect. I started as a first in-house recruiter at a social media startup. Six months later I was Head of People — not because I asked for it, but because someone left and the company still needed to go from 4 to 40. So I figured it out. That’s kind of been the whole theme. Five years at an agency. $1M+ biller. President’s Club every year. Genuinely loved IT recruiting and was perfectly happy being great at it — until I wasn’t happy with how the industry treated people anymore. So I left. Built my own agency from scratch with no clients, no tools, and no idea how to run a business. Hired coaches, got loud on LinkedIn, and ended up with 100% inbound clients because I refused to be quiet about what I was seeing. Then I figured out that AI could do in an hour what used to take a week — and I never looked back. I vibe coded an entire federal contracting platform. Built sourcing engines in Clay that turned outbound recruiting into pipelines companies actually own. Showed up on podcasts talking about the future of talent before most people were ready to have that conversation. Now I’m VP of Talent & Workforce Strategy at Fractal, building their entire talent function from zero, and leading AI adoption across the org because I've lived what's possible when you actually use these tools. Here’s my honest take on where this industry is going: the recruiters and talent leaders who don’t understand the technology aren’t going to survive the next five years. Not because AI is replacing them, but because the ones who do get it are going to be so far ahead it won’t be a fair fight. The gap is closing fast- I'm here to help people get to the other side of it. https://claracontractai.com/ Mom of three. LEO wife. Technical Recruiter OG. Builder at heart.

Experience

15 yrs 2 mos
Total Experience
3 yrs 5 mos
Average Tenure
1 yr 4 mos
Current Experience

Fractal

VP, Talent and Workforce Strategy

Mar 2026Present · 1 mo

Oliver tech connect

Founding Member

Dec 2024Present · 1 yr 4 mos · Orlando, Florida, United States · Remote

  • Founder and builder of an automated recruiting system using Clay, Lemlist, and Airtable. We’re moving away from relying on inbound applications and traditional recruiting agencies and instead building inbound pipelines where the company owns the talent pool and can hire from people who are already familiar with the business.
  • We use AI to analyze public data from places like GitHub and Discord to identify talent most companies never reach. From there, I design personalized outreach that actually feels human, including video job descriptions and tailored messaging instead of generic recruiter emails.
  • The model is subscription-based, which gives companies predictable hiring costs instead of paying 20% placement fees every time they need to hire. It allows teams to build a repeatable pipeline and hire from it again and again, while saving a significant amount of money over time.
  • I still own the company, but the day-to-day operations are run by my team.
Automated recruiting systemAI analysisPersonalized outreachSubscription-based modelRecruitingAI Implementation

Htc global services

Lead Client Partner- The Walt Disney Company

Dec 2023Dec 2024 · 1 yr · Orlando, Florida, United States · Hybrid

  • Led TA for Disney's newly formed AI Center of Excellence

Peersource

Senior Technical Recruiter (Agency)

Oct 2018Sep 2023 · 4 yrs 11 mos · Denver Metropolitan Area

  • Top Producer and multi-year Presidents Club Winner. Contract and perm recruiting.

Fanhero

2 roles

Founding Recruiter

Dec 2016Apr 2017 · 4 mos

  • First internal recruiting hire, promoted to Manager of Human Capital within 6 months
  • Scaled team from 4 to 50+ employees across engineering, product, QA, design, and GTM within 18 months
  • Served as sole internal recruiter and embedded hiring advisor during hypergrowth (seed)

Manager of Human Capital| Recruiting & HR Manager

Apr 2016Oct 2018 · 2 yrs 6 mos

  • 0-1 human capital function
  • Built and managed human capital programs spanning recruiting, onboarding, performance, and employee development, supporting scalable growth and improved workforce stability.

Softrock

Technical Recruiting Manager- HRBP (In-House Startup)

Nov 2010Apr 2016 · 5 yrs 5 mos · Orlando

RecruitingTeam scalingTalent acquisition

Education

University of Central Florida

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