Why Recruiting Tech is (Still) Not Helping Candidates and How to Fix It

“There’s this massive imbalance between the employer side of the recruiting equation where they’ve got all the tech, they’ve got all the weapons… Candidates don’t have anything.”–Doug BergIn this episode, I’m joined by Doug Berg, head matcher and big kahuna at Match2, a longtime builder and operator in the talent technology/recruitment space and the only guy I know that wears flip flops to HR Tech..Doug has lived and hacked nearly every iteration of online hiring — from fax machines and early internet job fairs to today’s AI-powered recruiting chaos.Doug and I have lived parallel lives in some sense. We have both been on the scene as recruitment went on-line and have continued to wage war against the barriers that are blocking successful hiring. But Doug’s unique experience building recruiting focused tech helps us take a very well rounded perspective.Doug and I trace the psychology of hiring systems, why most recruiting technology still fails both candidates and employers, and how efficiency-driven design has quietly stripped humanity out of the process.We talk about what broke, why AI is making some problems worse before it makes them better, and what a candidate-centered future could actually look like if we stop designing hiring like a transactional funnel and start designing it like a relationship.Topics Discussed & Key Insights1. Hiring Has Always Been Psychological — Ignoring That Is Why It BreaksDoug shares early recruiting stories that reveal a core truth: people don’t make job decisions based solely on skills or titles. They’re driven by values, aspirations, lifestyle preferences, and identity. Yet most hiring systems still treat people as static records instead of dynamic humans.Music to the ears of a psychologist like me!2. Applicant Tracking Systems Were Built for Control, Not for CandidatesWe unpack how applicant tracking systems were designed for compliance and efficiency — not engagement. The result:* One-way transactions* Forced applications* Zero room for curiosity, context, or conversationDoug explains why this original design choice still haunts modern hiring.3. AI Isn’t Breaking Hiring — It is Amplifying the Broken PartsAI didn’t invent hiring dysfunction — it amplified it. Candidates now apply to dozens of jobs at once using bots. Employers respond with more screening, more filters, more automation.The outcome? More noise. Less signal. Worse experiences on both sides.4. Real Hiring Happens Through Interaction, Not “Efficiency”Doug tells stories about simple interventions — like proactive chat on career sites — that led to real hires for impossible-to-fill roles. The lesson is clear: when candidates are allowed to participate instead of comply, hiring actually works.5. Hiring Will Stay Broken Until Candidates Control Their Side of the SystemOne of the central ideas in the episode: candidates have never been given real agency. Doug explains the structural imbalance:* Companies control the systems* Candidates adapt or disappearWe explore what changes when candidates control their own data, preferences, and relationships — and why that shift matters.6. The Resume Is a Dead Artifact — Identity Needs to Be PortableResumes are outdated snapshots. Doug makes the case for living profiles, portable personalization, and persistent relationships that move with the candidate across employers.AI finally makes this possible — not by enforcing rigid taxonomies, but by interpreting relevance across skills, experience, and context.7. The Future of Hiring Should Feel Like Reconnection, Not RejectionWe close by zooming out. Doug shares a simple but radical vision: if someone gets laid off on Friday, they shouldn’t start from zero.They should already know:* Who wants them* What they’re worth* Where they fitHiring shouldn’t feel like rejection roulette. It should feel like an intelligent market reconnecting human supply and demand.Final TakeawayHiring doesn’t fail because people are hard to assess.It fails because we designed systems that ignore how people actually choose, trust, and engage.AI won’t fix that on its own.But used thoughtfully — with psychology, agency, and dignity baked in — it might finally help us build hiring systems that work for humans again. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit charleshandler.substack.com