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In this episode of Now to Next, Jason Averbook sits down with HR tech veteran Doug Berg, known as the “Kevin Bacon of HR Tech” for his deep connections across the industry. Doug shares his entrepreneurial journey—from building Techies.com during the dot-com boom, to founding Jobs2Web (later acquired by SAP/SuccessFactors), to creating ZapInfo (acquired by Indeed), and now his latest venture, Match 2, which aims to fix one of recruiting’s biggest problems: the broken candidate experience. Doug and Jason dive into why candidates still face repetitive, siloed processes, how companies lose great talent through poor systems, and why the future of talent acquisition must flip from job-first to candidate-first. Highlights: Doug’s journey from programmer to recruiter to serial HR tech entrepreneur Lessons from Techies.com, Jobs2Web, and ZapInfo that shaped Match 2 Why “apply or goodbye” is a broken model for career sites The difference between personalization and individualization in candidate experience Why AI can’t solve talent’s biggest challenge—data silos How Match 2 acts as a “USB connector” for candidates, companies, and platforms The future of connected, bi-directional candidate relationships Guest: Doug Berg is a serial entrepreneur and innovator in the HR technology space. He has founded multiple successful companies, including Techies.com, Jobs2Web (acquired by SAP/SuccessFactors for $100M), ZapInfo (acquired by Indeed), and now Match 2, which focuses on fixing the broken candidate application and data-sharing experience. Known as the “Kevin Bacon of HR Tech,” Doug has been building solutions that connect talent and companies more effectively for over two decades. His mission has remained constant: to make recruiting faster, more human, and more efficient for both sides of the hiring equation. Follow Jason Averbook: Substack: https://substack.com/@jasonaverbook X: https://x.com/jasonaverbook LinkedIn: / jasonaverbook Instagram: / jasonaverbook YouTube: / @nowtonextwithjasonaverbook Facebook: / jasonaverbook Follow Doug Berg: LinkedIn: / douglasberg Email: Doug@match2.jobs Timestamps: (0:00) Introduction (0:50) Doug Berg's journey from retirement to HR tech innovation (3:30) The origins and impact of techies.com (4:49) Development and growth of jobs2web (7:18) ZapInfo's launch and acquisition by Indeed (9:40) Unveiling the Match 2 concept and application challenges (13:25) Personalization vs. Individualization in HR (15:05) Overcoming resistance to HR innovation (18:33) Match 2's influence on the job market and HR integration (22:41) Match 2's role in enhancing job search experiences (24:06) Match 2's deployment and competitive edge (27:25) Enhancing post-employment engagement through Match 2 (31:20) AI's role in job matching and addressing overqualification (32:31) Match 2's value during economic downturns (34:01) Closing remarks