CTO Coaching

CTO Coaching: A Guide for Leaders

I’ve spent 25 years scaling product and engineering teams, and one thing I’ve learned is that the hardest part of being a CTO is not about technology. For most CTOs and engineering leaders I know and have worked with, it’s not technical competence that holds them back. It’s the leadership aspects of the job that […]

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AI Reshaping CTO and CPO role

In 25 years of working in and around technology leadership, I’ve watched a lot of shifts. But how AI is changing the CTO and CPO role feels different from anything I’ve seen before. It’s not just in how software gets built, but in what it means to lead a technology organization. The boundary between product […]

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Podcast: Optimizing Tech Teams & Strategy In EdTech

In this executive leadership episode of EdTech Elevated, Lisa March, President and Founder of Partner in Publishing, interviews Leigh Newsome, Partner at Hoola Hoop and New York University adjunct professor. This episode focuses on scaling EdTech companies through navigating the complexities of technology leadership. Drawing from his experience as both a Silicon Valley engineering leader […]

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Beyond the Code: Executive Coaching for CTOs and CPOs

Chief Technology Officers (CTOs) and Chief Product Officers (CPOs) navigate the complex intersection of technology, product strategy, people leadership and business objectives. At Hoola Hoop, we offer specialized executive coaching tailored to the unique challenges faced by these tech leaders. Let’s start by dispelling some common myths about CTO and CPO coaching. Common Myths About […]

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Product and Technology Due Diligence

In mergers, acquisitions, and investment decisions, comprehensive product and tech due diligence is crucial for informed decision-making and risk mitigation. This strategic evaluation process examines critical areas including technical debt assessment, architectural decisions, R&D investment analysis, and team capabilities evaluation. Beyond surface-level code review, it provides deep insights into a company’s technological sustainability, product validation, […]

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The Essential Pillars of CTO Leadership: A Strategic Guide

As a Chief Technology Officer (CTO) in today’s dynamic tech landscape, mastering the core responsibilities of technology leadership is crucial for organizational success. Through years of CTO coaching and technology leadership experience at Hoola Hoop, we’ve identified four fundamental pillars that determine a technology executive’s effectiveness and impact. Whether you’re a new CTO or a […]

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