In this episode, host Sara Sheehan welcomes Jed Ayres, the visionary CEO of ControlUp, a leader at the forefront of digital employee experience and autonomous IT operations. Jed reflects on his early years owning and operating a hotel and restaurant, where performance feedback was immediate and ruthless. These formative experiences shaped his servant leadership philosophy, which emphasizes empathy, accountability, and trust as the foundation of high-performing organizations. Jed’s unique journey reveals invaluable lessons in leadership excellence and transformational leadership.
Jed explains how the shift to remote and hybrid work during the pandemic revealed a critical gap in traditional IT operations. While companies spent years prioritizing customer experience, employee digital experience lagged behind. This lag created friction, anxiety, and lost productivity. From that, Jed led the evolution of ControlUp from a deep technology platform into a cutting-edge, unified digital employee experience solution. As organizations navigate the complexities of the digital employee experience, understanding the human element becomes essential. He clarifies the difference between managing technology performance and managing employee experience, highlighting how real-time telemetry, automation, and AI eliminate repetitive troubleshooting and dramatically lower ticket volumes. Gartner predictions support this shift, suggesting organizations that fail to adopt these platforms risk falling behind operationally and competitively.
Sara and Jed discuss how AI transforms IT from a reactive cost center into a strategic enabler. By using real-time data contextualized around individual employees, AI can identify issues, recommend fixes, and even remediate problems. This not only reduces operational drag but also frees IT teams to focus on higher-value strategic work. Jed also addresses common misconceptions about DEX, urging organizations to prioritize core IT operational efficiencies before venturing into HR aspects. This strategic alignment is crucial for fostering an environment where talent can thrive, ultimately leading to organizational growth and innovation in leadership.
From a leadership perspective, Jed emphasizes that successful digital workplace transformation requires executive sponsorship, cross-functional collaboration, and cultural readiness. Successful organizations formalize digital employee experience at the board level, invest in dedicated ownership, and commit to long-term partnerships rather than isolated tool deployments. With these accelerating changes in how we work, Jed emphasizes the urgent need for seamless technology experiences that empower employees and enhance productivity. This episode is not just a conversation; it’s a clarion call for transformational thinkers to embrace change management strategies that cultivate workplace culture and enhance communication in leadership.
The episode posits a bold prediction: In the near future, manual troubleshooting will be viewed as reckless and wasteful. Autonomous IT operations powered by AI will become the standard, fundamentally reshaping how organizations operate and how leaders think about productivity and human potential. Don’t miss out on this opportunity to engage with one of the industry’s leading voices in business transformation. Tune in to Transformational Thinkers with Sara Sheehan and discover how to transform challenges into opportunities for growth and success.
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About Jed Ayres:
Jed Ayres brings vast experience in leading multinational software organizations to ControlUp, successfully executing strong organic and inorganic growth strategies, building groundbreaking leadership teams, executing strong partnerships, and expanding internationally. Most recently, Ayres served as CEO of IGEL, where he was instrumental in its acquisition by TA Associates and positioning it as a market leader. Prior to that, Ayres was responsible for the strong growth in category leader AppSense (acquired by Ivanti) and held executive leadership positions with MCPc (acquired by Logicalis), MTM Technologies, and GE Capital IT Solutions.
Key Moments:
00:00:01 – Welcome and Introduction to Jed Ayres
00:01:30 – Hospitality Roots and the Servant Leadership Mindset
00:03:00 – Why Digital Employee Experience Became a Strategic Imperative
00:04:45 – The Hidden Cost of Poor Technology Experiences at Work
00:06:20 – Optimization vs Monitoring in Digital Employee Experience
00:08:10 – From Legacy IT Tools to Real Time Data and Automation
00:10:00 – Why AI Is Perfect for Eliminating Repetitive IT Work
00:12:45 – Reframing DEX as a Business Outcome for CEOs and Boards
00:15:30 – Tool Consolidation and the Financial Impact of Automation
00:18:00 – Cutting Through Data Noise with AI Driven Insights
00:20:15 – Frontline Workers, Brand Experience, and Digital Friction
00:23:20 – Common Misconceptions About Digital Employee Experience
00:26:15 – DEX as the Gateway to Autonomous Endpoint Management
00:29:45 – Leadership, Trust, and Empowerment in Transformation
00:45:10 – A Bold Prediction for the Future of Work and IT Operations
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Contact Sara Sheehan | Sara Sheehan Consulting:
Contact Jed Ayres | ControlUp:
- Website: ControlUp.com
- LinkedIn: JedAyres
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