37: Scaling, Strategy & Survival: The CTO Playbook for Large Enterprises with Sarah Greasley

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Sarah Greasley is an IBM Distinguished Engineer turned CTO with over 40 years in tech, known for leading large-scale transformation projects at companies like IBM, Direct Line, and AWS.

In this episode, you’ll learn how to lead complex tech projects without getting lost in details, make tough calls when short-term goals clash with long-term needs, and understand why managing technical debt is a leadership issue, not just an engineering one. Sarah shares practical ways to align thousands of people, how language, culture, and clarity impact success.

Sarah was EMEA Director for Solution Architecture at AWS, leading a 1,300-person team, supporting over 612,000 customers, and driving AI, diversity, and inclusion initiatives. Before that, she was Group CTO at Direct Line Group, delivering tech strategy, architecture, and £100m+ programs, transforming the business for 5 million UK customers and doubling gender diversity in tech. Earlier, Sarah was IBM Technical Director and Distinguished Engineer, creating architectures for major financial services clients.

Timestamps:

[0:00] Introduction

[03:30] Moving from IBM to Direct Line Group

[05:10] The importance of purpose in career decisions

[06:30] Handling complexity between program goals and enterprise needs

[08:00] Leading with alignment in large organizations

[09:45] Reading between the lines in communication

[10:50] Different meanings of risk in insurance

[12:00] Learning to ask better questions instead of having all the answers

[13:30] Losing technical expertise and shifting to architectural thinking

[15:00] Cloud migration challenges at Direct Line

[16:30] Building scalable cloud solutions with performance testing

[17:55] Moving away from legacy mainframes

[18:50] Lessons from working on ATMs in the 1980s

[20:00] Building future leaders and emotional intelligence in teams

[21:30] Managing technical debt during high-stakes changes

[23:00] Human capital and specialist knowledge in legacy systems

[24:20] Aligning org structure with tech for adaptability

[25:40] Using analogies to explain technical debt

[27:10] The role of allies in building inclusive cultures

[28:30] Subtle meeting dynamics and how to navigate them

[29:50] Writing inclusive job specs that attract more women

[31:10] The importance of visible female role models

[32:20] Emotional intelligence as a leadership skill

[33:40] Thinking beyond tech: money and the business view

[35:00] Learning to let go and trust your team

[36:20] Building consensus in large enterprises

[37:40] The value of “disagree and commit”

[40:40] Structural changes that enable diversity and inclusion

[41:45] Leaving IBM after 33 years and embracing change

[43:00] First three things to do as a new CTO

[44:30] Owning your schedule and not apologizing for it

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Follow Sarah Greasley on LinkedIn

Resources Mentioned:

CTO Academy | Website

Radical Candor by Kim Scott | Book or Audiobook

Disagree & Commit by Justin Kuester | Kindle

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.