Simon Ingleson is the founder & Managing Director of RosterElf, a cloud software that handles all SME staff management tasks, including rostering, payroll, and more.

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1) To kick things off, could you tell us a little about your career background and current role?

Most of my career was at News Corp. I started there straight after uni, selling car ads in the classifieds, back when classifieds existed. It was my first real corporate job, and I ended up staying there for 15 years, which wasn’t the plan.

 I stayed because I had a fantastic CEO named Ish Davies, who boot camped me and took me under his wing. After many years he’s recently retired from News Corp and was just a great guy. His way of mentoring me and helping me grow was career changing. 

I worked my way up in Perth, Western Australia, all the way up to advertising director. I remember the day of being promoted like it was yesterday. I was 28 years old, and at the time, I had all of three direct reports. I was running a magazine we had launched, and the ad director who was my boss resigned, and I got pulled into Ish’s office. He said, “Congratulations, you’ve now got 150 staff, the job’s yours.”

It was exciting and scary, but Ish didn’t just dump me in it; he supported me, he mentored me. He knew that I had some skills to learn, and through this, I stayed at News Corp for a long time. 

After multiple offers in the later years to go to Sydney, I eventually said yes. The director in Sydney was across all the products there, so print, magazines online, and a huge team. So that was a real insight into the head office and business operations. Mr Murdoch had his office upstairs for when he was in the country, and it was a unique experience dealing with that calibre of people. 

I was doing a lot on the tech side as News Corp was transitioning from traditional newspapers to online media. I enjoyed the fast pace of change and new challenges, which ignited my entrepreneurial spark.

I decided one day, much to everyone’s shock, that 15 years was enough, and I had this weird entrepreneurial bent that wasn’t going away. So, I resigned with their blessing, gave my heap of notice and moved on, but I wasn’t quite sure at that point what to do.

I did some consulting and then decided to open a Mexican franchise restaurant. Probably not the best business decision ever, but that’s ultimately how RosterElf came about.

I had about 40 staff across two stores, and managing the complexities of shift-based companies, be it hospitality, retail, etc., is more than just a little challenging. I faced the complexities of managing a small business and needed better solutions. Unfortunately, when I went to find the answers, nothing jumped out as a viable option. 

And that was how RosterElf was born from humble beginnings. 

It was very much a side project for a few years, but I piled a lot of my own money in, worked for zero, and got to the point where the business was gaining traction. So now I’m the managing director of a fast-growing tech start-up that’s working to scale across the globe.

2) What does a day in your life look like for you? Can you take us through a recent workday?

I guess one of the adjustments from News Corp is that you have an HR department, an IT department, and a collection of other departments to support you. You don’t have any of that when you’re building a fast-growing tech company. My day is pretty much plugging the gaps. 

One day I can be jumping into marketing and helping there. The next day I can be jumping into sales. Day three, I’ll be jumping into support, and that’s either strategically or often still hands-on when the business needs me.

I see my role as trying to steer a ship and be aware of where the pressure points are as we grow and try to jump in and support and spend as much time with the team as I can to take pressure off. 

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

As a business, we’ve transitioned to a mixture of face to face and remote work. We’re a tech company, and you don’t need everyone sitting next to each other. So, after managing global teams over the last few years, we’re almost remote first.

We’ve got fantastic online systems to support our activities, but it’s still critical to get the balance right. It’s been a challenge building culture as it’s a real shortcut having people together each day. If there are issues or concerns, you can address them straight away. You can misread a Slack message much easier than you can misread a one-on-one conversation. 

But we have a hybrid model, and the sales guys are in less often because they’ve just got to be on the phone. Marketing, tech, customer support, et cetera, spend a few days in the office, a few at home. It’s working well, and I think that’s the reality of where the business and many others will go.

For me, it works well. I get time to think when I’m working from home, and as my staff often know, I come up with these crazy ideas between 10:00 PM and 3:00 in the morning, which means if I’m up till 3:00 in the morning, I don’t have to be bright-eyed and bushy-tailed at 9:00 AM. Then, I blow-up everyone’s inbox and Slack channels with some ideas, and people can review and respond in turn. 

4) What does work-life balance mean to you, and how do you work to achieve that goal?

I’m not going to write a book on it at the moment because I don’t have it. It is tough when you are at this life stage because I’m constantly thinking even when I’m not working.

I’m thinking about strategies in the business. I’m thinking about shareholders. I’m thinking about the next round of funding. I’m thinking about how we’re going to launch overseas. I’m thinking about how to get the most out of the people. 

On that one, I’m not currently very good at that, is the honest answer. If you see me with bags under my eyes, there’s usually a reason, but it’s something I’ve got to work on as we grow. It’s been a while since I’ve had a break, and I don’t think I’ve had a holiday in the last few years where I have entirely not thought about the business.

However, it is my goal for the year to take some downtime because you can only push so much. It’s not like you can easily avoid this stage, but you can get through it. 

I do, however, know myself well. I’ve got epilepsy which probably doesn’t go great with this career choice, but it guides me and helps me ensure I don’t stress too much. I have learned the lesson of not pushing myself over the edge, and I know when to stop. Sometimes I’ll text the guys and go, “I’m having the day off,” and they all step up and defend the fort whilst I clear my head.

We are rapidly growing, and it’s exciting. Our leadership team lets me have that space where I don’t need to be involved so much day-to-day, and we’re not far away.

5) In the past 12 months, have you started or stopped any routines or habits to change your life?

I walk every morning; that’s my thing these days. I’ve got two dogs who don’t care in the slightest about RosterElf, and that is a great thing. My morning routine is a six o’clock wake up, and I’ll walk for an hour or two hours with the dogs. It clears my head and flushes out everything that has stressed me out overnight and yesterday. 

For me, it’s like a morning meditation. Animals are funny. They don’t worry about what humans do, which helps you break your state. So that’s something I’ve done. I used to swim a lot, and that’s something I miss, and again, it’s on my list for this year, is getting back in the pool. You can’t overthink while you’re swimming; otherwise, you’ll probably drown. It’s a good way I find to turn off.

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

I’ve got quite a few books I read, but I’m a classic Googler. When I’ve got a problem, and I don’t know how to solve it, I’ll Google it, and I’ll Google it because I’ll get 50 different opinions from vastly different sources, and I’ll then weigh it up, and I’ll think about it. I do love Google. 

I set a goal for at least a book a month with reading, and I’m currently on track which is a nice boost to feeling on top of things. I essentially don’t read business books, but I read many personal development books.

I think that’s probably the bit that is most important when you’re running a business; it’s people and personality. If you can improve yourself, you improve how you interact and relate, and you’ll struggle to change anyone else. 

As for reading suggestions: If you haven’t read Simon Sinek’s Start with Why, it is a classic and has aged well. Deep Work by Cal Newport is a critical read for driving personal performance, and The Power of Habit by Charles Duhigg will give you the ability to master yourself.

7) Are there any products, gadgets, or apps that you can’t live without?

I can just about run my business on my phone these days, our support board and CRM development board via ZenDesk, our team comms on projects via Slack, our Development pipeline on Jira, and our marketing feeds via Google Analytics and SEM Rush.

I have, however, set a goal for my year. I’m going to delete a few apps and focus on keeping the critical ones. Do I need to know everything every 15 minutes? Probably not. So, I can live without some of them, to be honest, as you grow the business, you want to hand over functions to your team and trust them to run with it. Letting go.  

It’s a big focus for me. I’ve got a great team, and I want to have fewer gadgets and apps, not more; I think I can live without many of them, to be honest.

8) If you could read an interview about work-life balance by anyone, who would that be?   

I think it was Ish back at News Corp. I’ll never forget when he said to me, “You start a new role. You’re feeling under pressure. You’re feeling stressed.” And he said, “Stress is all relative.” And I’ll never forget it.

Ish would say, “Look, you think you have stress. Imagine being the President of the United States,” what do we do with global security, energy, health, and the wellbeing of our people? So, it’s all relative, and you realize that over your career, as you step up, you laugh about the stuff you used to stress about before. 

These days I love hearing interviews or even talking to people that I meet who are in high-pressure roles, well above what I’m going through. If they’re honest, they will say they’re stressed, and it’s nice to know you’re not alone, but you realize they’re coping with 5, 10, 20, 100 times or more stress than you are.

So, it gives you a perspective that the world doesn’t end, and they struggle with stress. I think anyone in an environment where they have pressure struggles with stress. I think it’s just the nature of the game, but stress helps you perform, so it’s getting that balance right.

It’s about understanding that it’s relative, and there are times when you need to suck it up. You’re not running the United States. You’re not making global decisions. You’re just running a fast-growing tech company, so take a deep breath and put it in perspective.

9) Do you have any last thoughts on work, life, or balance that you’d like to share with our readers?

I’m going to give you stuff that I’m not doing yet, but I want to do. Get off devices. 

There’s a reason the Zuckerbergs and the like don’t want their kids attached to devices. It’s what that does to your subconscious and the requirement to feed that constantly.

So, I think my two tips are to start the morning with a routine that clears whatever’s good, bad, or otherwise, and delete some apps. If you can’t bring yourself to delete them, turn off all their notifications and move the apps to the last screen on your device.

They’re two things that I’m working towards, and I’ve already seen making a massive difference.

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