CTO coaching and mentoring for engineering leaders navigating scale, AI adoption, technical debt, and the transition from builder to executive.
You were promoted because you were a great engineer. But great engineers and great engineering executives require entirely different skills, and most organizations don't teach you how to make the leap.
Most CTOs and VPs of Engineering are technically excellent but were never taught how to lead an organization. They manage instead of leading, react instead of strategizing, and accumulate technical debt because they never had time to step back and architect a solution.
CTO coaching gives you the outside perspective, accountability, and frameworks to grow as a leader, not just a manager. It accelerates what would otherwise take years of trial, error, and burned goodwill.
Over 25 years, Leigh Newsome has worked with CTOs and engineering leaders at small and mid-sized companies to build engineering organizations that deliver consistently, scale gracefully, and attract strong talent.
Start the Conversation →Every engagement is tailored, but the work almost always touches these four areas. They're deeply interconnected, weakness in one tends to cascade into the others.
Leigh is a Partner at Hoola Hoop, a full-service executive coaching and advisory firm. He works alongside a team of partners and coaches to support you, from the boardroom to the engineering floor.
CTO coaching isn't just for CTOs. The challenges of engineering leadership show up across titles, company sizes, and industries.
Every client relationship is different. Whether you need focused 1:1 support, peer connection, or broader team development, there's a format that fits.
The core engagement. Regular coaching and mentoring sessions focused on the leadership, strategic, and organizational challenges you're navigating right now. Tailored to your stage, your company, and your goals.
Small-group peer sessions organized around a shared challenge, managing up to a CEO, navigating AI adoption, org restructuring, and more. Curated cohorts mean everyone in the room is working through something similar.
Broader leadership development beyond the CTO, for senior managers, VPs, and full engineering leadership teams. Structured programs and group coaching tailored to your org.
Leigh Newsome isn't a typical executive coach. He has been an engineer, and he has been a CTO - he has lived the full arc from writing code to running large engineering organizations as a CTO. That practitioner experience is what separates his coaching from those who have only observed the role from the outside.
Most CTO coaches have one track. Leigh has several including software development, hardware engineering, audio systems, analytics and holds many issued US patents. A background in psychology and software development gives him an unusual lens: he understands how systems break, and why the people running them do too.
The difference between an engineering organization that thrives and one that barely survives usually isn't technical, it's leadership.
Over more than two decades, Leigh has worked with engineering leaders at companies ranging from early-stage startups through public companies, across fintech, health tech, SaaS, and consumer technology. Leigh launched CTO Coach NYC more than 10 years ago. It was long before CTO coaching and mentoring became a recognized discipline to bring structured, experienced coaching to engineering leaders who are often the least supported in an organization. The CTO is expected to have all the answers, but rarely has anyone to think out loud with.
Leigh is a Partner at Hoola Hoop, a full-service executive coaching firm serving CEOs, CTOs, boards, and investors at growth-stage companies. He focuses on 1:1 CTO coaching and, through Hoola Hoop's team of coaches, can support broader leadership development across your entire engineering organization.
Leigh is also an Adjunct Professor at New York University, teaching advanced audio and web engineering in the Master's degree program, reflecting his cross-disciplinary technical background.
Practical thinking on the challenges CTOs and engineering leaders face most often. No fluff, just actionable perspective from the coaching room.
The quarterly roadmap is becoming mismatched to the operating tempo most engineering orgs now face. A look at the continuous planning cadence that is replacing the quarterly review cycle.
Read on Hoola Hoop →AI is making the CPO–CTO partnership explicit. The synthesis work that used to absorb disagreement is being automated away, which means CTOs and CPOs need a joint operating system that actually holds.
Read on Hoola Hoop →A new shape of engineering team is quietly winning the operator phase of AI, smaller, more senior, with different roles and metrics. What AI-native team topology actually looks like in 2026.
Read on Hoola Hoop →Most CTOs have shipped agents. Very few have scaled them. Why some organizations are compounding value while others see pilots stall, and the five things that separate them.
Read on Hoola Hoop →Token leaderboards are the new lines of code, they look rigorous, travel well in a board deck, and reward the wrong behavior. Why tokenmaxxing took hold and what the scoreboard that actually matters looks like.
Read on Hoola Hoop →Should your CTO and CPO be one person or two? There is no universal answer, but AI is changing the urgency of the question. A clear-eyed look at the role convergence debate.
Read on Hoola Hoop →Deploying AI agents has become the easy part. Most engineering organizations are doing it faster than they can govern it, and that gap is where real risk accumulates. The governance framework every CTO needs in 2026.
Read on Hoola Hoop →Technical due diligence requests arrive at the worst possible time, mid-fundraise, mid-acquisition, mid-everything. A guide for engineering leaders who want to be prepared before the request lands.
Read on Hoola Hoop →Boards have moved from "what's your AI strategy?" to "what did it cost, what did it return, and how do you know?" A guide for CTOs navigating the AI ROI conversation in 2026, and how to build the case credibly.
Read on Hoola Hoop →Managing up is the skill most technical leaders are never taught. Learn what CEOs actually need from CTOs and CPOs to build trust, alignment, and stronger executive partnership.
Read on Hoola Hoop →The shift to agentic development is changing software delivery and engineering leadership itself. A practical guide for CTOs rebuilding process, teams, and strategy for an AI-native SDLC.
Read on Hoola Hoop →The hardest part of being a CTO isn't technology, it's leadership. For most engineering leaders, it's not technical competence that holds them back. It's the leadership aspects of the job that create the real challenges.
Read on Hoola Hoop →AI is changing not just how software gets built, but what it means to lead a technology organization. The boundary between product and engineering is shifting in ways that every tech leader needs to understand.
Read on Hoola Hoop →Leigh Newsome joins the EdTech Elevated podcast to discuss scaling EdTech companies through technology leadership, drawing from his experience as both a Silicon Valley engineering leader and executive coach.
Read on Hoola Hoop →CTOs and CPOs navigate the complex intersection of technology, product strategy, people leadership, and business objectives. A look at what specialized executive coaching for tech leaders actually involves, and what it isn't.
Read on Hoola Hoop →In mergers, acquisitions, and investment decisions, comprehensive product and tech due diligence is crucial. A deep dive into technical debt assessment, architectural decisions, R&D analysis, and team capabilities evaluation.
Read on Hoola Hoop →Through years of CTO coaching, four fundamental pillars have emerged that determine a technology executive's effectiveness. Whether you're a new CTO or a seasoned leader, these are the areas that matter most.
Read on Hoola Hoop →How to prepare for investor and M&A technical due diligence before the request arrives, including what evaluators look for and the common mistakes CTOs make.
Read on Hoola Hoop → Watch video on ELC →New York has one of the densest concentrations of engineering leadership talent in the world, and some of the most unique pressures that come with it. We work with CTOs in the NYC tech community and serve clients globally.
The first step is a no-pressure discovery call. We'll talk through where you are, where you want to be, and whether coaching is the right lever. No commitment required.
Or reach out directly at ctocoach@ctocoachnyc.com