Balancing the Grind with Jeremy Gupta, Chief Operating Officer at

Jeremy Gupta is the Chief Operating Officer at, a SaaS platform that enables car dealerships, OEMs, Rideshare and other emerging automotive subscription providers to offer their own vehicles for subscription to customers.

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

I’ve got a background in Computer and Biomedical engineering but fell into a Software Engineering pathway after University as it offered better career prospects at the time. From there I progressed from software engineering through to management and CTO roles before eventually agreeing to join a startup, Loopit after consulting with them for a few months.

As CTO I helped build version 1.0 and turn it into the leading car subscription platform in ANZ before moving to my current role as Chief Operating Officer earlier last year. Nowadays I’m responsible across all the internal teams with a view to ensuring we are operationally equipped to achieve the (big) goals we’ve set ourselves.

We’ve just wrapped up raising a seed round which gives us the capital and partners to move internationally and grow our market share further.

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

Given the variance in teams I am responsible for I try to theme one day a week on a certain core area – e.g. Mondays might be Engineering, Wednesdays People & Culture and so on.

I read Jack Dorsey did this so that he could appropriately lead both the Twitter and Square (now called Block) teams so I thought if it works for someone like him then I’m sure it would for me! I tried it out in a previous role and it helped immensely with clarity on what is important in any given day so I’ve adopted it ever since.

Based on that I usually set aside time for deep work before the kids get out of bed and then use the rest of the morning for meetings in a core area before keeping the afternoons free where possible. I’ll occasionally throw in some admin post dinner once or twice a week to keep things ticking over but I do my best to keep from 5-7:30pm meetings free and for family time.

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

For me it means achieving the outcomes both I and others set for myself in my professional and personal life. Being in technology I’m grateful of the flexibility it offers me in terms of ways or working and working “hours” – which in turn allows me to be present in my personal life for things that pop up week to week like school drop offs/pickups and after-school sport. Without clear goals none of that is possible so work-life balance starts there.

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

Post lockdown I’ve been very conscious of separating time for deep work vs “busy” work which wasn’t always possible when the kids were at home being home-schooled! This enables me to get through the strategic aspect of my work life while also keeping the tactical work ticking over and preventing myself from being a blocker to anyone or team.

Exercise has also been a key habit that I’ve got into a better rhythm with – deliberately carving out time in the day when working from home gives me a second life post exercise instead of the day or my energy levels dragging.

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

Most of my books, podcasts and newsletters all orient to my work life so are typically centred around operating and growing SaaS businesses like Loopit. There’s too many to mention but I’d be happy to go into more detail if someone wanted more detail around it specifically

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

Jack Dorsey. Please tell me he does actually theme his days and it does work!

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

Everyone has different personal and professional lives not to mention genetic makeup which can dictate how and when they are the most productive. Just because it works for someone (Jack Dorsey apart) doesn’t mean it’ll work for you so experiment your way to balance and productivity and don’t stake it all on a 4am wake up and regular classes of lemon water just because you read somewhere that it works.

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About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.