Top 17 CTO Coaches to Learn From in 2026

Andy Skipper is founder and CEO of CTO Craft, the leadership community he launched in 2017 after CTO roles at Made.com and Comic Relief and extensive interim technology leadership work.

Through CTO Craft, Skipper helps senior technology leaders build the skills, resilience, and commercial perspective needed for the role. His coaching and mentoring draw on experience across startups, scaleups, investing, and one of the field's largest peer communities.

Eric Weiss is the CEO of Chaos to Clarity and a CTO and executive coach with two decades of technology experience spanning Sony, Raytheon, Qualcomm, startup leadership, OpenAI, and coaching.

Weiss helps CTOs and technical founders grow their organizations without slowing their teams down. His CTO Operating System covers hiring, team structure, roadmaps, goals, executive leadership, and working with boards. His advice comes from his own experience building and leading technology teams.

Leigh Newsome is a CTO coach, partner at Hoola Hoop, and NYU adjunct professor. He spent more than 25 years of experience building and leading product and engineering organizations across industries.

A former CTO and engineering operator, Newsome coaches technology leaders from startups through public companies. His work covers executive leadership, organization design, product and AI strategy, technical debt, board communication, and the transition from hands-on builder to senior leader.

Brad Henrickson is a technology leadership coach and seasoned operator. His career spans founding Zoosk, VP Engineering roles at Keen.io and Earnest, and CTO leadership at Scoop and Change.org.

Through Henrickson Leadership, he works with technical founders and technology leaders on priorities, decision-making, organizational design, hiring, product-engineering collaboration, executive relationships, and the human side of scaling high-growth companies.

Adelina Chalmers is founder of The Geek Whisperer and a strategic adviser to CTOs and other STEM executives, with experience working across technology, science, and engineering organizations.

Chalmers helps CTOs connect technical work with business strategy, communicate with boards and executives, secure funding for engineering priorities, and handle leadership or performance issues. She also teaches executive communication at Cambridge and Oxford.

Joel Chippindale is a CTO coach and mentor at Monkey's Thumb with more than 20 years leading software teams, including CTO roles at Unmade and Econsultancy and CTO/COO leadership at FutureLearn.

Chippindale supports startup and scaleup CTOs as their teams and companies evolve. His coaching draws on firsthand executive experience and focuses on faster learning, better decisions, leadership development, communication, culture, and sustainable team performance.

Jossie Haines is an executive and engineering leadership coach and former VP of Engineering at Tile. She has more than 25 years of experience in software engineering and over a decade in technology leadership.

Her coaching helps Directors, VPs, and CTOs step into bigger roles, lead strategically, build executive influence, and avoid getting trapped in execution. Haines draws on leadership experience across Tile, Apple, Zynga, and other technology organizations.

Laura Tacho is an engineering leadership coach and technology executive. Her career includes CTO at DX and leadership roles at CloudBees, Aula Education, and Nova Credit, plus developer tools work.

Tacho coaches CTOs, VPs, and senior engineering leaders on organizational performance, executive presence, accountability, succession, and product collaboration. She also teaches data-driven engineering leadership, including developer productivity and AI-impact measurement.

Jason Noble is CTO, lecturer, and coach at CTO Academy, bringing board-level technology experience across software businesses, enterprise projects, innovation, and technical leadership.

At CTO Academy, Noble helps technology leaders strengthen strategic and operational decision-making. His background spans software entrepreneurship, technical sales, agile delivery, complex enterprise programs, and executive roles, giving his coaching a broad operator's perspective.

Hywel Carver is co-founder and CEO of Skiller Whale, a former startup CTO and technology adviser who has spent years building companies, coaching tech leaders, and convening CTO peer communities.

Carver helps engineering teams build the skills needed to support their technology strategies. His experience as a CTO, coach, and community builder shapes his practical approach to developing leaders, growing teams, and strengthening technical skills.