1. What have you found most challenging as a CEO or executive of a large enterprise?

Communication and focus.
If only communication were as easy as saying or writing something, the real challenge is in how people interpret what you say/write. How often do you see an organisation where teams are on a different page to each other, and everyone has a different perspective on what the company strategy is?
At a leadership level, communicating one to one, or even to a group is only the tip of the iceburg. You need to learn to operationalise your communications if they're really going to stick and help create clarity.
This means you need to be consistent. You need to document your comms, share it in 1:1s, across all hands, in docs, during inductions, in casual conversations, in newsletters...you need to communicate until you're utterly bored by saying the same thing. And even then, you need to test to ensure it's penetrated to every layer...you should include it in company-wide surveys and find other ways to objectively test how well understood your communication is.
And then there's focus. As you can imagine, if communication is that hard...communicating lots of ideas or changes in direction will be a challenge multiplied tenfold! And yet as a leader you're going to be exposed to so many ideas every day. From your team (and theirs), clients/customers, other leads, books etc.
It's important to expose yourself to all these ideas and feedback; and it's even more important you evaluate and say no to 99% of them. Every new initiative could be a winner, but it could equally be a huge drain on resources too. The more focussed you are as a leader and an organisation, the more likely you are to succeed in those areas. Spreading yourself too thin is a recipe for disaster, but it takes a lot of discipline to say no to so many great ideas every day!
Finally, bringing both challenges together, it's just as important to communicate clearly and consistently what you're not doing (and why) as it is to say what you are working on. It saves a huge amount of time and energy across the company by ensuring razor sharp focus on executing against what matters. A 'don't do list' is possibly even more powerful than a 'do list'!

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

It's not been a straight line!
I left University unsure what I really wanted to do, but knowing I wanted the opportunity to keep learning and enjoy as much autonomy as I could.
I found myself in the conference industry, which was a wonderful early experience that exposed me to many different markets and leaders; allowed me to work across sales, marketing and operations; offered international travel; and made me a mini-business owner from the get-go.
I was enthralled by the world of technology, and so decided to launch my own tech startup. After that entrepreneurial stint of 18 months and going through the 'school of life' I was keen to learn from a tech 'Unicorn' and joined Eventbrite to see how great companies operated at scale.
From there I decided to go to the other end of the spectrum, and joined a very early stage startup - Attest - where we grew rapidly from 10 to over a 120 people when I left; and now I currently run a functional revenue team of just over 80 people across 3 continents at Student Beans.
If I were to highlight the common threads that run through my career there would be three: calculated risk, accountability and impact.
While I believe it's important to stick to a role and commit to a company, there will often be a time when your learning curve can be accelerated in a new environment, so weighing up those two forces is tricky and making the move will always be a calculated risk.
Wherever you are, it's important to always give your all and be 100% accountable. Speak up if you believe the company can do better. Try new things and innovate even if it feels like that's above your 'pay grade'.
And work hard to deliver results, no matter what barriers you face. Don't be afraid to fail, as long as you learn fast you'll ultimately be rewarded.

3. How do you structure your work days from waking up to going to sleep?

I aim to get up between 6 and 6.30 so I have time before the kids wake up and set my intention for the day.
I enjoy a black coffee and get a little life admin done or reply to emails first thing, then do exercise - typically running, yoga, pilates or weights - before getting ready for the day.
Food is really important to me, so I (almost) always ensure I have time to cook and eat a proper breakfast before the work day really kicks in.
My work days are very meeting heavy, ranging from 1:1s with my direct reports to team meetings, project catch-ups to planning sessions. This is the best way to provide the support and enablement needed for the team to succeed.
I usually manage a break for lunch, before an afternoon of more meetings.
I always make a point of ensuring I catch-up with other leaders from different industries to share best practices, and I also make time to provide coaching to startup founders each month.
My work day is typically done around 6pm (from a meeting perspective) and I'll cook dinner.
In the evenings when I have my girls (aged 5 and 6), we play lots of games and hang out. On other nights I'll catch up with my partner or friends.
If I have work to catch up on I'll be online again from 9, but I try not to work past 10.30.
I round off most weekdays reading a book and aim to be in bed by 11.

4. What's the most recent significant leadership lesson you've learned?

Leadership doesn't happen in a bubble. You can have the clearest idea about where you're going, but if there's not explicit alignment across the whole leadership team then it's all but impossible to effectively execute against those plans.
To help overcome this, there's a great tool discussed in an excellent book, the Five Dysfunctions of a Team, and popularised by its use at Amazon: Disagree and commit.
With a disagree and committed approach to decision making at the leadership level, you can mine for dissent and ensure absolutely everyone has contributed their genuine thoughts on a particular topic (this is essential). Inevitably in a room full of leaders, consensus rarely emerges, but by having the debate and knowing everyone's opinion has been heard and considered, the final decision will gain more buy-in.
And so once a direction has been decided, even if it doesn't align to your original viewpoint, everyone must (after disagreeing), now commit. They can't work to undermine the outcome or ignore it, the position becomes one everyone gets behind, and this helps generate stronger cross-functional and organisational alignment.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The One Minute Manager series is wonderful. I was given the original book when I became a manager for the first time. It had a profound impact on how I approached leadership, and much of it has stuck with me. From the importance of providing clarity to the power of positive reinforcement, it contains many great lessons.
Two subsequent books on delegation and situational leadership are equally useful parables that have informed my approach to leading people and teams for many years.

6. How do you build leadership capacity in a large enterprise?

There are three key aspects you need to consider: model behaviour, hire well, make meetings effective.
On modelling behaviour, you have to 'walk the walk' when it comes to living your leadership principles. For example you can't preach a work life balance, and then fire off messages all hours of the day and weekend. Or say that punctuality is essential and then turn up late for meetings (or allow yours to overrun). What you say and do have to be absolutely congruent, otherwise you're communicating a mixed message. However if you are able to act on what you say consistently, this is modelling behaviour and others will start to emulate you.
The second aspect of modelling behaviour is ensuring promotions, rewards and other public recognition reinforces the behaviour you want to see. For example you can't have a 'no assholes' policy and then promote a salesperson who's the biggest asshole just because they closed the most deals.
On hiring well, it's essential you hire for future potential and not just past experience. If you want to bring leaders into your business, you need to create a process that hires for a growth mindset and cultural diversity. You then need to build a people model around these hires than encourage innovation, failing fast, open feedback, psychological safety and coaching to allow your future leaders to develop.
Finally, you need to ensure meetings are effective. They often feel like a heavy tax on your time, and leaders complain all the time about being in too many meetings. But Andy Gove, the legendary former CEO of Intel, has a different perspective. Meetings offer one of the largest operating leverages a leader can exert across the organisation. You just need to know what you're trying to achieve from and approach them with the right focus and agenda to maximise their impact.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

When I left my last role, I had so many amazing messages and feedback from the team, many of whom I stay in contact with.
There were two that really stood out though. One person said I'd helped change the course of their career through offering coaching/guidance and giving them opportunities to prove themselves; while the other said the freedom and trust they had meant they were able to achieve their best work.
I don't mean this to be self-aggrandising, but the leadership lessons I took from it were twofold:
1. Don't just measure your impact in terms of revenue or business outputs. You're privileged to be in a position to help shape others' career, so remember the human element of leadership.
2. Your impact is often measured by what you don't do e.g. giving the space and freedom for your team to chart their own path, rather than feeding them the answers.