About Sidekick

We help founders (and other busy humans) escape admin overload by pairing them with hand-picked assistants who protect their clients' most valuable resource; time.

We're a small team of kind, big-hearted, excellence-obsessed people who genuinely love helping people thrive.

We’re looking for a highly capable, detail-loving, get-things-done kind of human to join us as a Sidekick, someone who thrives on bringing order to chaos, staying one step ahead, and making life easier for the people around them.

If you enjoy variety in your day, take pride in doing things properly, and like the idea of being a trusted right-hand in both business and life admin, this might be for you.

The Role

This is not your typical desk job. It’s a dynamic, hands-on role that blends property management, financial admin coordination, and business support.

You’ll work closely with a founder to keep things running smoothly behind the scenes, from making sure properties are guest-ready to ensuring deadlines aren’t missed and systems stay organised.

This is an in-person role based in Newlands, with regular trips to a property in Claremont.

Key Responsibilities

1. Property Management

• Oversee a rental property in Claremont (3 tenants in one house)

• Take full ownership of Airbnb management when applicable, including:

• Guest communication (friendly, responsive, and on point)

• Check-ins, check-outs, and making sure everything runs like clockwork

• Manage tenant relationships, leases, and admin

• Coordinate maintenance, repairs, and service providers (and make sure things get done properly)

2. Personal Financial & Administrative Support

Think of this as bringing calm and clarity to the numbers and paperwork.

• Liaise with tax advisors and accountants (you’ll coordinate, not do their job)

• Keep track of documents, deadlines, and follow-ups (ensuring nothing slips through the cracks)

• Track and organise expenses across different entities

• Keep financial records neat, structured, and easy to understand

3. Business Support

• Help coordinate proposals and performance reports

• Manage diary scheduling and meeting logistics

• Work alongside a small, focused team

• Over time, there’s an opportunity to grow into a para-planner role

Who We’re Looking For

You’re the kind of person who doesn’t wait to be told, you notice, think, and act.

You take ownership, solve problems early, and genuinely care about doing things well.

You’ll likely be:

• Highly organised (you love a good checklist)

• Detail-oriented (you notice the small things others miss)

• Proactive and resourceful (Google & Claude are your besties, but so is Common Sense)

• Calm under pressure and good at prioritising

• A clear, confident communicator (you’re comfortable speaking up and suggesting better ways)

• Warm, professional, and easy to work with

• Trustworthy and discreet

• Someone with strong judgement — you just get it

Skills & Experience

• A background in bookkeeping or financial admin understanding is a big plus

• Strong written and verbal communication skills

• Tech-savvy and comfortable using tools (including AI)

Compensation, application process & other FAQs

Please visit our Careers page.

Good luck!

Some people are just wired to help. If that's you, and you take quiet pride in doing things properly, we'd love to hear from you. All the best with your application, we're rooting for you