Emily Mikailli: Women’s careers have moved on — the career ladder hasn’t

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There is still an unspoken belief that careers should follow a familiar upward path: you join, you learn, you progress, and then you keep climbing up the corporate ladder. That thinking shapes everything from promotion cycles to performance reviews.

It assumes everyone is always aiming for the next step in the same way, at the same pace. But that model was never built around the realities of modern women’s working lives. Acting as though it fits everyone only makes the gap harder to ignore.

My own career is a prime example of why the metaphorical ladder falls apart. I qualified as a solicitor, then moved into talent acquisition — first at Google, then SurveyMonkey — when I saw how my legal training could apply differently.

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Midway through SurveyMonkey, I made what seemed like a sideways step, leaving recruitment to take on a broader people-focused role. It didn’t read as progress on paper, but it gave me the foundation to build Signifyd’s HR function from the ground up.

I spent over a year out of work after having my first daughter. I wouldn’t change that time for anything, but it was the longest stretch of time I hadn’t worked since being old  enough to have a job. That break changed what I wanted from work and what I was willing to prioritise.

I came back with a different set of criteria for how I wanted to spend my time at work. But according to traditional frameworks, a year-long absence registers as a problem to overcome rather than a legitimate part of someone’s professional journey. None of these choices fit the upward-only narrative, yet all of them made me more effective at what I do now.

We’re measuring the wrong things

The pivots and pauses in a career are often where the real growth happens: a lateral move that expands your skill set or the time spent building depth rather than chasing the next title. These experiences don’t show up as progress in traditional performance systems but they’re often what prepare someone for the complexities of leadership.

From my own experiences, drive doesn’t always look like relentless upward motion. Sometimes, staying power matters more than speed. Over thirty or forty years, the people who last might be the ones who know when to step back or when to move horizontally to build capabilities they’ll need later.

The problem is that our systems all assume linear progression is the only kind of progression worth pursuing.

The best careers rarely move in straight lines

I’ve seen this play out at Signifyd over the best part of a decade. In the early days, careers developed beyond traditional ladder rungs; people would spot a gap, step into it and then often find themselves doing something completely different from the role they were originally hired for. There was far less focus on whether it formally counted as a promotion; what mattered was whether it helped move the business forward.

Growth requires frameworks. You need to be able to tell people the steps they should take to progress and develop, but frameworks tend to harden. They start rewarding one kind of story – the person who joined as an individual contributor, became a manager, then a senior manager, then a director, all within the same function.

Some of our best leaders don’t have that story. They’ve zigzagged across teams or spent time building expertise in areas that barely existed three years ago even if it didn’t come with a better title. The trick is preserving space for that kind of growth even as the organisation matures.

Building organisations around real employee needs

Organisations often treat flexibility as accommodation: someone needs to work from home two days a week and that arrangement gets locked in. But people’s needs shift constantly.

Rigid flexibility isn’t flexibility at all. What works is ongoing conversation between managers and their teams about what’s needed, coupled with evaluating people on what they deliver rather than when or where they deliver it. That’s harder than implementing a policy, but significantly more effective.

This matters especially at senior levels. There’s an assumption that people have “figured it out”, but senior leaders face the same tensions around time, energy and competing demands — they’re just less likely to raise them. They need managers and boards who recognise that sustainable performance doesn’t mean being available at all hours. Leadership also sets the template. If every executive took the same route to the top, that tells everyone else what success is supposed to look like, regardless of what the policy documents say.

Retention isn’t something you fix with an initiative when someone’s considering offers elsewhere. It’s what happens when people feel seen and understood throughout their time with you. That means career systems that recognise impact regardless of how long it took to achieve. Flexibility embedded in how you operate, not positioned as a benefit for special cases. Leadership that visibly represents multiple paths, not just multiple faces on the same path.

The aim isn’t to make room for non-linear careers as a concession. It’s recognising they’re how most careers work, particularly for women. Organisations that accept this don’t just retain more people. They get access to talent and perspectives they’d otherwise lose.

Chief People Officer at 

Emily serves as Chief People Officer and Chief of Staff to the CEO at Signifyd, where she leads global people strategy for the world's leading commerce protection platform. Since joining the company in 2016 , Emily has been instrumental in scaling Signifyd into to a global organisation with offices across San Jose, London, Belfast, and New York.

Emily specialises in building goal-driven, proactive HR frameworks that support rapid innovation. Prior to Signifyd, she held leadership roles at SurveyMonkey, where she headed recruiting for front-office teams, and earlier worked at Google, gaining experience in global talent operations.

Emily holds a Bachelor's degree from Duke University. Beyond her corporate work, she previously served as Vice Chair of the Board of Directors for Parisi House on the Hill - a residential treatment programme for mothers and children.

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