Jobtrees, the career platform known for its extensive database of real job paths from thousands of professionals, today announced the launch of Ollie, the first AI Career Assistant built on actual workforce progression data rather than generic AI predictions. Ollie is designed to help jobseekers explore career options, plan next steps, refine resumes, and navigate the job market with guidance rooted in real-world experience.
As millions turn to AI for job searching—yet most remain unsure of how to use it effectively—Ollie introduces a fundamentally new kind of career support: AI that is grounded in authentic career journeys, real role transitions, and verified workforce insights collected across the Jobtrees platform.
“Career tools have traditionally served employer needs. Ollie changes that by putting jobseekers first—giving them the data, clarity, and direction they need to move forward,” said Sarah Fales, Director of Career & Recruitment Content at Jobtrees.
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Unlike typical AI chatbots or resume generators, Ollie uses Jobtrees’ structured dataset of more than 4,000 job titles, thousands of mapped career paths, and employee-driven insights to generate guidance that reflects how people actually advance in their careers.
“AI tools are everywhere, but most lack real career progression data,” added Fales. “Ollie bridges that gap. It interprets real paths taken by real professionals and turns that data into personalized direction. Combined with our resume builder, it’s the most powerful free tool available to jobseekers.”
Recent surveys from Jobtrees reveal:
72% of jobseekers don’t know how to use AI effectively during their job search
90% trust advice from real employees over generic guidance
The average jobseeker submits 32 applications to secure just 4 interviews
Ollie addresses these challenges by transforming Jobtrees’ proprietary career-path data into clear, actionable, personalized career plans.
While most AI tools rely solely on language model output, Ollie blends AI with a verified, structured dataset of:
Career paths
Job transitions
Real employee insights
Skills and role requirements
Advancement timelines
This hybrid approach produces guidance that is:
Grounded in actual career stories
Tailored to the user’s experience and goals
Specific, realistic, and highly actionable
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