Cape Town, Western Cape, South Africa · Hybrid
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, …
Skills: Property Management, Financial Administration, Airbnb Management, Bookkeeping, Diary Scheduling
Cape Town, Western Cape, South Africa • Hybrid
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The role involves managing a rental property in Claremont, including Airbnb guest communication and maintenance coordination. Additionally, the assistant provides financial and business support by liaising with accountants and managing schedules for a founder.
The ideal candidate is a proactive, detail-oriented individual with strong organizational skills and a professional demeanor. A background in bookkeeping or financial administration and proficiency with AI tools are highly preferred.
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.
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.
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)
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
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
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
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)
Please visit our Careers page.
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
An Exceptional Support Service for Seniors. Stay Independent. Be Connected. Live Fully.
Sidekick provides exceptional, on-demand personal assistance to seniors, enabling independence, enriching lives and delivering peace of mind. Your personal assistant, concierge, helping hand, friendly companion. Sidekick Concierge is not a healthcare provider nor are Sidekicks a substitute for registered nurses or home health-aides. Sidekick Concierge does not provide any medical care. Visit us at http://sidekickconcierge.com
Offices: New York, US
View all jobs at Sidekick Concierge Inc.An Exceptional Support Service for Seniors. Stay Independent. Be Connected. Live Fully.
Sidekick provides exceptional, on-demand personal assistance to seniors, enabling independence, enriching lives and delivering peace of mind. Your personal assistant, concierge, helping hand, friendly companion. Sidekick Concierge is not a healthcare provider nor are Sidekicks a substitute for registered nurses or home health-aides. Sidekick Concierge does not provide any medical care. Visit us at http://sidekickconcierge.com
Offices: New York, US
View all jobs at Sidekick Concierge Inc.