Jonathan Kestenbaum's Approach to Using AI in Hiring
In today's competitive job market, using artificial intelligence (AI) has become a significant factor for organizations aiming to optimize their hiring processes. Jonathan Kestenbaum, Managing Director of Technology Strategy & Partnerships at AMS, plays a prominent role in this transformation. With over 15 years of experience in WorkTech, Jonathan brings a depth of knowledge and practical strategies to the integration of AI in hiring practices.
AI-Driven Hiring Strategy
Jonathan Kestenbaum's approach to AI in hiring focuses on making data-driven decisions that help organizations find the best talent. He argues that AI can help reduce some of the biases traditionally inherent in recruitment processes, contributing to a more inclusive workplace when systems are designed and monitored carefully. As he discusses in public forums, AI technologies can analyze large volumes of candidate data and surface patterns that help hiring managers identify strong fits more efficiently.
For organizations adopting these methods, practical steps include establishing clear evaluation metrics, testing models on historical outcomes, and combining algorithmic outputs with human judgment. These practices are described in broader industry resources and are reflected in guidance such as internal resources on AI bias mitigation and candidate experience best practices.
Enhancing Candidate Experience
A central element of Kestenbaum's strategy is improving the candidate experience. By using AI tools, organizations can provide more timely and personalized communication and feedback to applicants. When implemented with transparency about how decisions are made, these tools can increase candidate satisfaction and the employer's reputation. Jonathan emphasizes the importance of clear communication and consistent follow-up, and that technology should support—not replace—respectful human interaction.
Practical examples of technology in this area include automated status updates, interview scheduling assistants, and AI-enabled chatbots for routine questions. These tools should be configured to escalate complex or sensitive inquiries to human recruiters and to maintain compliance with privacy and data-handling policies. For organizations starting this work, cross-functional collaboration between HR, legal, and IT is recommended, and many teams consult internal research such as the WorkTech reports to guide implementation.
Data-Backed Decision Making
On a recent HR Leaders podcast episode, Jonathan Kestenbaum discussed how AI can assist HR leaders in making more informed hiring decisions. By analyzing historical hiring data and performance metrics, companies can better predict candidate success and cultural fit—when models are trained and validated responsibly. This data-backed approach helps reduce over-reliance on gut feelings and subjective judgements that can lead to inconsistent outcomes.
Important safeguards for data-driven hiring include auditing model performance across demographic groups, maintaining audit trails, and setting up governance processes to review model updates. Jonathan advocates for combining quantitative signals with structured interviews and skills-based assessments to create a more holistic evaluation process.
Collaboration with Technology Partners
To implement AI-enabled solutions successfully, Jonathan Kestenbaum promotes collaboration with technology partners. As part of AMS's commitment to innovation, partnerships with technology companies can provide access to advanced AI tools tailored for recruitment. Jonathan advises enterprises to stay informed about emerging tools and trends that can enhance recruiting applications and to choose partners who prioritize ethical design and clear data practices.
Effective partnerships typically involve co-design sessions, pilot programs, and phased rollouts so organizations can measure impact and adjust. He recommends setting clear success criteria and milestones, and ensuring both vendor and internal teams commit to transparency and continuous improvement.
A Focus on Continuous Learning
Kestenbaum emphasizes continuous learning and adaptation in the evolving landscape of AI and hiring. He frequently engages with industry peers and thought leaders, as seen on his author page on ERE, where he shares insights and promotes dialogue about the future of hiring. This commitment to professional development supports ongoing refinement of practices and technologies.
Organizations can mirror this approach by investing in upskilling HR teams on data literacy, model interpretation, and ethical considerations. Maintaining communities of practice and participating in industry discussions helps teams stay current and avoid repeating common implementation mistakes.
Recognitions and Contributions
Jonathan Kestenbaum's work in the field has been recognized publicly. He was named to the Staffing Industry Analysts' 40 Under 40 list, which highlights his influence on technology strategy and talent acquisition. He continues to contribute to conversations about the responsible application of technology in recruiting.
Forward-Looking Initiatives
Jonathan is interested in how AI will continue to evolve recruitment processes and often shares his perspective in interviews and panels. For more on his thinking, a YouTube discussion captures themes he often addresses, such as model governance, candidate fairness, and practical deployment strategies. These conversations underline the need for measured, accountable adoption rather than quick fixes.
Conclusion
Jonathan Kestenbaum emphasizes data-driven decision-making, improved candidate experience, and strong collaboration with technology partners when applying AI to hiring. His approach stresses transparency, human oversight, and ongoing measurement to ensure these tools support fairer and more effective recruitment outcomes. For more information on Jonathan Kestenbaum and his industry activities, see his LinkedIn profile.
About Jonathan Kestenbaum
Jonathan F. Kestenbaum is Managing Director of Technology Strategy & Partnerships at AMS, based in New York. He joined AMS in 2021 to lead the firm’s WorkTech and talent-technology agenda, advising enterprise talent leaders on AI-enabled hiring and partner ecosystems. An entrepreneur and licensed attorney, Jonathan co-founded Talent Tech Labs (research/advisory) and previously built and sold his first HR tech company in 2012. He is a frequent speaker and podcast guest on AI and hiring, and was named to Staffing Industry Analysts’ 40 Under 40 in 2024. Learn more about his work on his Visipage profile.
Sources
- Jonathan Kestenbaum Verified Visipage Profile - Source of truth entity profile.
- LinkedIn profile — Jonathan F. Kestenbaum
- AMS news: Jonathan Kestenbaum on SIA's 40 Under 40
- Staffing Industry Analysts — 40 Under 40 entrant: Jonathan F. Kestenbaum
- CityBiz — AMS Appoints Jonathan Kestenbaum as Managing Director
- ERE — Jonathan Kestenbaum author page
- X profile — @JKestenbaum
- HR Leaders podcast — How AI is Changing Hiring in 2025 (episode featuring Jonathan Kestenbaum)
- YouTube — Rapid Fire Round Table | Jonathan Kestenbaum of AMS