The AI ROI Pressure Point The conversation has shifted. Most CTOs are not struggling to invest in AI, but they’re struggling to account for it. Boards that spent 2024 asking “what’s your AI strategy?” are now asking “what did it cost, what did it return, and how do you know?” Those are different questions, and […]
What Your CEO Actually Needs From You. Managing up is the skill most CTOs and CPOs never got taught. Your good at building teams, shipping product, and navigating technical complexity. The relationship with your CEO is a different kind of problem, and quietly, it’s where some of the most capable technical leaders I coach and […]
From SDLC to Agentic SDLC I’ve lived through a lot of process evolutions. The move to agentic development is different in kind, not just degree. It’s changing what it means to lead an engineering organization altogether. CTOs aren’t asking “should we use AI?” anymore. That debate is over. They’re asking: how do we rebuild our […]
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 […]
In 25 years of working in and around technology leadership, I’ve watched a lot of shifts and coached many CTOs and CPOs. 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 […]
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 […]
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 […]
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, […]
Preparing for Technical Due Diligence Technical due diligence requests arrive at the worst possible time — mid-fundraise, mid-acquisition, mid-everything. The engineering leaders who handle them well aren’t the ones who scramble. They’re the ones who were already prepared. It’s common for engineering leaders to receive technical due diligence requests on behalf of an investor or […]
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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