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Balancing the Grind with Jenna Leo, CEO & Co-Founder of Like Family

Jenna Leo is the co-founder and CEO of Like Family, a Sydney-based impact tech-startup connecting carers with people who need a helping hand.

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

I started my career as a finance management trainee in a large FMCG. It was a great place to build career foundations and I had the opportunity to work across all aspects of the finance department, understand what really drove the business, and learnt how to communicate with stakeholders across the organisation.

I also was supported to go to The College of Law, acquire my accounting qualification, and work on a secondment to Japan for 3 months and experience an entirely different culture!

I then expanded my experience to encompass a mix of finance, marketing, and sales in an entertainment company where, because it was a smaller business, I had the opportunity to get closer to the setting of the strategic direction and seeing how the budget impacted results and ROI.   

At the same time, I did my yoga teacher training, and it was as a yoga teacher that I discovered my passion for helping people and also got my first taste of entrepreneurialism, which later led me to start Like Family.

As a founder, my role is consistently evolving as the business grows.  As CEO, my main focus is on future strategy planning and ensuring we have the resources to deliver our ambitious goals.  

When we first started this was creating the business model and plan, creating the MVP, speaking to customers and setting up the legal structure and financial requirements.

Now my role as CEO is to ensure alignment to the strategy across the entire business and taking accountability for ensuring the strategy is effective to hit our goals. And, as we move from a startup to scaleup my role is to develop our culture and values and ensure we’re building a team of high performers who are also focused on the value we contribute to our community.

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

Here’s my day today: 

Jack is awake at 6am so Mat and I are up! We pop him into a carrier and head to our local cafe, baby bottle in hand, for a coffee and breakfast to connect on the top work and personal issues plus diary scheduling for the week.

At 8am, my mum arrives and I hand over Jack to head to my home office. Today, I’m working from home so I head to my desk to review my schedule, plan out my week, and read up on an issue that I’m thinking about.

Top of my mind today is how I can best lead the team for an effective goal session that meets our ambitious OKRs. I check my emails and manage my to-do list by smashing through small but urgent tasks and quick wins.

At 11am, Jack is awake from his nap, so I take a work break to feed him before passing him back to my mum.

Then I have a VC one-on-one to catch up with a member of my team.

At 12.30, I have lunch with my mum and Jack outside on our deck to enjoy the sunshine.

At 1.15pm I prepare for our weekly Like Family leadership team meeting and share the agenda.

The next hour is dedicated to interviewing a candidate for an open role to assess skills and cultural fit.

At 3:00pm I run our weekly leadership meeting.

From 4.30-6.30pm, I’m in deep work. I don’t know why but this time of day tends to be my most productive for focused work.

Around 6.30pm, I feed Jack and put him to bed before Mat and I cook and have dinner together.

At 8.00pm, we have what we call our “Hour of Power” before singing off for the day. Both Mat and I set one hour to crack through a key task that requires some dedicated time. 

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

Because we’ve been working remotely since Covid, it’s allowed us to be more flexible and be open to continue being flexible for the whole Like Family team.

My current role has a mix of thinking, collaboration and communication and collaborating and communicating when my team is available is important. But the thinking and getting things done can be done flexibly as long as it’s delivered to the team and stakeholders in time to ensure they have what they need from me to stay on track.

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

I try to be flexible in the way I manage my week so that I can fit in quality time with my family, ensure I’m on top of the work and available to my team, and also fit in time for my own health and wellbeing.

My first child, Jack, is just 8 months old so my life changed a lot this year.  My husband is also my Co-Founder of Like Family, so we have a lot of ‘work’ conversations when we’re not ‘working’. But when you’re passionate about something it really doesn’t feel like work.

The challenge is to maintain that passion and balance is key to helping that.  Before I had Jack I could easily ‘overwork’ myself because I love what I do and it didn’t matter how many hours I worked, as long as I could go to yoga or for a walk.

Now work-life balance is different because I need to care for Jack and want to get play time with him each day and I also want to give myself time to go to yoga and exercise and if I can, get some sleep too!

So, that might mean rising at 6am some days to get a couple of hours of work complete before the rest of the household needs me, heading back to my desk after I put Jack to sleep at 7pm or sneaking in a few hours on the weekend. On the flipside, it allows me to care for Jack, take him to baby yoga, go to pilates, get my work done and get the right mix of work and play into my life.  

Having this flexibility for our team as well is really important.  We are focused on collaboration, outcomes and results, not on clock-watching.  

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

All my old routines went out the window when I had Jack so this year has been the year of new and extreme discipline! I’ve had to give myself more flexibility and increase my efficiency to ensure I have time for everything that’s important. My discipline levels have reached new heights! 

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

The First Round Review blog for interesting articles  https://review.firstround.com/ 

For inspiration, the “How I Built This,” podcast makes for fascinating listening.

The Lean Startup is a must read and go-to as a startup founder.

And when things are hard I love to turn to the book, The Hard Thing about Hard Things which makes my problems seem like molehills!

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

I couldn’t live without Google Docs. The ability to edit and share makes a really big difference in collaboration, especially while we all work from different locations.

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

I’d love to hear more from founders who are a couple and also have children.  I’m still searching for them.

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

Work-life balance is different for everyone and is also different depending on your stage of life. It’s about finding a rhythm that works for you, building a flexible but driven team who can support that, and also being open to change.

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About Author

Balance the Grind is a work-life balance publication on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.