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In a recent Startmate Collective (fka. Ladymates) session, Kate Andrews, ex-CTO at CipherStash, gave us a rare behind-the-scenes look at what it really takes to lead at the highest level in tech.

But not the shiny version - the version that’s lived-in, hard-earned and so very memorable.

What makes Kate stand out isn’t just her technical skill or incredible career (35+ years in tech and counting) - it’s how openly she shares the real stuff: the sliding door moments, the awkward mistakes, the life re-prioritisations and the deeply human lessons that shaped her into the leader she is today.

Here’s are a couple of the lessons she shared: 

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💥 Lesson 1: Risk isn’t reckless it’s a privilege

Kate started her career in UI development, but when her company was acquired, she was reassigned to actuarial COBOL programming.

“I hated it. I was taking sick days wherever I could. I just hated the idea of getting out of bed and going to work.”

Then she saw a newspaper ad that read, simply: “Are you a bored programmer?”

She called the number. That phone call set her on a new path one that aligned better with her strengths in psychology, communication, and empathy. The role was in technical writing. She didn't even know it existed.

“That risk ended up paying off. I learnt early on that taking risks can have great returns but I also learnt that being able to take a risk is a privilege. Not everyone can. So take them when you can. And be grateful.”

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👊 Lesson 2: Don’t wait to be picked

During the conversation, Kate reflected on how asking the right question can quietly shift how you're seen. When a male peer was quietly being considered for a Head of Engineering role and she wasn’t Kate asked the CTO a question that changed the game:

“What would I need to do to be the obvious choice next time?”

She planted the seed and within a week, she was invited to apply. She got the role.

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💬 Lesson 3: Kindness > Niceness

Kate admits she spent the early part of her leadership career being “catastrophically nice.”

“I’d sugarcoat feedback so much that people would walk away thinking, ‘That was a great conversation. I’m doing so well.’ But niceness is about you. Kindness is about them. Be clear that’s the kindest thing you can do.”

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🔥 Lesson 4: You don’t have to know everything

At one point, Kate found herself envious of a colleague who had every Jira ticket tracked in a mega spreadsheet. She tried to emulate it… and realised it was a trap.

“He knew everything. But he couldn’t see the big picture - and his team didn’t feel trusted. I learnt to get comfy with not knowing.”

If you're aiming for a CTO role, here's your permission slip: You don’t need all the answers. You need the right people around you, and the humility to let them shine.

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Kate's story isn’t about a perfect roadmap to the top. It's about navigating leadership with humour, integrity, and deep awareness of the humans around you - including yourself.

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She’s not just a CTO. She’s the kind of leader who makes space for others to grow.

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✨ Want to learn from leaders like Kate?

Kate is a member of the Startmate Collective Leaders a community for women and non-binary people in leaders, operators and founders who want to grow and learn from those just a few steps ahead.

These sessions (like the one you just read about) happen because of members like Kate. If you're intrigued by a future in leadership - especially in tech - this is your place.
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👉 Apply to the Startmate Collective

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