sidekick

Kindness and Excellence

 See open roles

Build a world that’s organised and kind.

Sidekick pairs (brilliant & wonderful) personal and executive assistants with (busy & appreciative) clients.

See open roles How hiring works

Are you…

Tick all that apply

Well then, you’ve found your people!

So what do Sidekicks do?

Since 2021, 74 Sidekicks have been getting ducks in a row for 163 clients: executives, NGO directors, ambitious founders and busy working parents. See examples of tasks below.

Personal assistance

You take over the life admin that eats your client’s evenings, weekends and inner peace.

  • Play calendar ping-pong and wrangle someone’s schedule before it wrangles them
  • Plan the trip to Eataly, right down to the visas, flights (that exclude a 14-hour layover in Dubai), baggage limits and pasta points.
  • Find birthday, anniversary and Christmas gifts that are thoughtful, on time (and not a regift of granny’s bath soaps)
  • Plan & organise meals that are thoughtfully curated to your client’s needs
  • Be the person who anticipates your client’s personal needs like booking doctor’s appointments, scheduling that overdue eye test, and more.
  • Decode a medical aid claim before it becomes a 6-month saga
  • Keep the finances from becoming a shoebox of receipts and good intentions
  • Take their car in for a service before they know it’s due
  • Deal with Home Affairs, SARS, Vodacom and the bank, so they never sit on hold again.
  • Handle the school forms and keep the lift club running.
  • File the IDs, policies and tax certificates so anything’s findable in 10 seconds.

Business/Executive assistance

You protect your client’s time and focus by taking everything else off their plate.

  • Tame the email and WhatsApp inbox that multiplies like rabbits – triaging, drafting, unsubscribing, replying and following up
  • End the calendar ping-pong by handling all things scheduling.
  • Guard their valuable time and ensure their calendar matches their priorities.
  • Turn chaotic notes, voice memos and meeting notes into neatly-organised and actionable tasks that you track to completion
  • Build and maintain the systems, standard operating procedures, meeting rhythms and information that keeps everything organised and everyone sane
  • Keep the money stuff moving – invoices, receipts and expenses
  • Build team culture and celebrate people – birthday cards, all-hands presentations, year-end events, the moments that matter
  • Manage socials so your client has a presence without it consuming their existence
  • Create the deep-dive research docs, slide decks, and spreadsheets your client keeps bumping to ‘when things are quieter’ (they won’t be)
  • Keep the office running – supplies, lunches, deliveries, cleaners, visitors, the stuff nobody notices until it stops working
  • Plan the work trip down to the last detail. Flights, hotels, transfers, restaurants, and the backup plan when something inevitably goes wrong.

What Sidekicks say

In their own words.

I’m surrounded by the most genuine people, who are always ready to lend a hand.

Being a Sidekick has been an incredible journey. The team took real care to match me with clients who suit my skills and working style, and they’ve provided continuous support to both the clients and me every step of the way. What’s truly opened my eyes is the community: I’m surrounded by the most genuine people, who are always ready to lend a hand. If you’re looking for flexible, meaningful work where you’re genuinely looked after, I can’t recommend being a Sidekick enough.

Alice
Cape Town

You’ll find great people, interesting work and a community that genuinely wants to see you succeed.

When I joined Sidekick, I was looking for great clients. What I found is a community that adds so much to the experience.

There is a genuine culture of people sharing knowledge, resources and practical help whenever someone needs it. It’s an incredibly supportive environment that helps you do your job well and feel part of a team.

The clients are another huge part of the experience. Sidekick connects you with an incredibly diverse range of businesses and entrepreneurs, from people building their first company to highly experienced founders and executives. The breadth of businesses and people you get to work with creates so many opportunities to learn and grow.

And behind all of this is a management team that genuinely cares about making an impact. They take what they’re building seriously, but they also know how to have fun along the way.

If you’re considering becoming a Sidekick, I’d say go for it. You’ll find great people, interesting work and a community that genuinely wants to see you succeed.

Shannon
Port Elizabeth

For me, it really is the best of both worlds.

I’m so thankful to be part of a community that genuinely cares and is always there for one another. I also love the freedom and flexibility that Sidekick gives me. I’m able to be home when my kids come home from school, be there for my “demanding” husband 😄, and still do meaningful work and help provide for my family.

For me, it really is the best of both worlds. I feel supported, valued and incredibly grateful to be part of the Sidekick community. 10/10 would recommend!

Areejh
Cape Town

It feels great having a proper support system behind you that actually cares about getting things done right.

Being a Sidekick has been such a great experience. They really took the time to find someone who fits how I work, which made all the difference. The support doesn’t stop after the match either, the whole team is responsive, thoughtful, and always willing to help. It feels great having a proper support system behind you that actually cares about getting things done right.

Zoey
Durban

This year alone, I’ve ordered nine cakes and counting!

I love being a Sidekick. It gives you a lot of freedom in your days. You get to choose what you’re going to do minute by minute, hour by hour. You get to meet lots of different people and deal with lots of different personalities every day. You get to do lots of fun and interesting tasks, and some not-so-fun ones too.

This year alone, I’ve ordered nine cakes and counting! Some days I’m stuck in a bog of admin, but other days I’m organising parties, dealing with caterers, or shooting content for one of my clients. When I think about the list of things I’ve done as a Sidekick, it’s actually crazy. I think my job as a mom, a wife, and just a human has set me up well to manage a job like this.

Nicola
Cape Town

It’s not just your typical virtual PA setup.

Sidekick and its team have a remarkable ability to match clients to the best sidekick. The team go above and beyond not only for their clients but for their sidekicks. They are also just a message away for anything you need. It’s not just your typical virtual PA setup. There is a genuine want to make someone’s life easier.

Amy-Jan
Botswana

A great sidekick is the person beside you who makes life a little easier.

Working at Sidekick has been such a refreshing experience. The culture is warm, encouraging and genuinely people-focused. It’s clear that the same care that goes into supporting clients also goes into supporting the Sidekicks.

What I love most about Sidekick is that the name really does capture what we do. A great sidekick is the person beside you who makes life a little easier. Someone who brings structure to the chaos, takes things off your plate, keeps the details moving and ultimately gives you back something incredibly valuable: your time.

Jubilee
Paarl

The day-to-day is never the same.

I’ve been at Sidekick for just under four years, and it’s been an amazing journey. I was matched with my clients almost instantly and connected with them from the start. I’ve grown so much as a PA, the day-to-day is never the same (planning a 5-day wedding festival one day and taking a beloved pet to hydrotherapy the next) and the support from management has been exceptional.

I’m very grateful to be here :)

Tate
Cape Town

Why Sidekicks stay

Save someone’s week, every week

When life gets cloudy with a hundred small things, you bring the order and clarity that let the light back in. It brings so much joy to the person you help. And somehow, even more to you.

No two days look the same. One day you’re planning a five-day wedding festival (with a spreadsheet so beautiful it could make you cry). The next, you’re finally getting your client to that specialist appointment they’ve been avoiding for a year.

Maya Angelou
“Try to be a rainbow in someone’s cloud.”
Maya Angelou Photo: York College ISLGP, CC BY 2.0

Work that fits around your life

Many roles are remote/hybrid, so you can shape your week, do school lifts and work from home. Be a present parent and take on rewarding work. Like Hannah Montana, you get the best of both worlds.

A Sidekick playing with a toddler at home

Earn well, without hassle

Earn R200 to R280 an hour, depending on your experience and your clients’ needs. With a full client load of 40 hours a week, that’s R25k to R39k a month (before tax).

Predictable income. Clients sign up for a set number of hours each month, so you know what’s coming in, even when a client goes on holiday.

No paperwork. We help with the contracts, invoicing, and chasing, and pay out your earnings monthly.

Matched with care

We take care of finding your clients, so you can focus on the work. We thoughtfully match you with founders, CEOs, NGOs and busy families doing big things, people who’ll truly value you. No awkward pitching, no chasing leads.

A client and his Sidekick smiling with a “Welcome to the Sidekick community!” box

You are not alone

As a Sidekick, a whole crew is in your corner.

  • Weekly online assemblies: AI, travel tips, solving stucks
  • The most helpful WhatsApp group in SA where genuinely kind people share knowledge, resources and practical help whenever someone needs it.
  • A Success team that’s always a WhatsApp away, and wants to see you thrive.
  • In-person meet-ups, because the people you message every day are even better in person.
A long table of smiling Sidekicks at a team dinnerSidekicks on a video call, celebrating a win with party emojis

What makes a great Sidekick?

Sidekicks are a particular kind of person. Here’s what the best ones have in common.

The must-haves

  • Fluent English
  • Driver’s licence and a car
  • Own working laptop and fast wifi
  • Love learning new tools (Claude, Notion and friends)

Qualities we love

The journey to become a Sidekick

  1. 1

    Apply

    Complete our application form. Real humans review all applications. You’ll hear back from us within 5 business days.

    Bring: energy, honesty & your CV.

  2. 2

    Work Simulation

    Experience two hours in the life of a Sidekick. Plus an interesting personality quiz.

    Bring: your A-game.

  3. 3

    Meet the Team

    Finally, a live interview!

    Bring: your authentic self and questions.

  4. 4

    Sidekick Academy

    Our onboarding & training course (created with love) that gets you ready for day 1.

    Bring: coffee.

  5. 5

    Get Matched

    We pair you with your clients whose needs match your strengths & style. Onboarding support included.

    Bring: champagne!

Questions? Good. We like curious people.

Most Sidekicks (about 90%) are independent contractors. Some clients need a dedicated full-time PA or EA, so Sidekick employs you and you work with that one client. Here’s how they compare.

Independent contractor You work with 2-4 clients to fill your hours. We match you with clients you’ll love working with, and we help with the paperwork & billing. Employee You’re employed by Sidekick and work with one client full-time. We stay on as your support and success partner.
Best for About 90% of SidekicksClients who need one dedicated PA or EA
Clients Usually 2 to 4. E.g. 4 clients at 10 hours a week each.One client, full-time
Hours 30 to 40 a week (ideally 40)40 a week
Drawcards Variety, a week you shape yourself, and you never rely on just one clientA steady routine and a deep partnership with one client
Your contract is with Each clientSidekick, permanent or fixed-term
Paid leave No, but you plan your own breaksYes
Tax Yours to handle. We’ll introduce you to our favourite tax guy.We handle your UIF and SARS deductions

Depends on the client. There are three flavours:

  • Hybrid: mostly remote, plus in-person bits like office days or taking the car for a service.
  • In-office: at the client’s office every day.
  • Fully remote: for clients in rural Eastern Cape, London, New York and beyond.

In-person roles are in Cape Town, Joburg, Durban, Pretoria, Gqeberha, and a growing list of other cities.

It helps. PA or EA experience and a relevant qualification will strengthen your application, but neither is essential. Some of our best Sidekicks had neither when they started. What matters most is judgement, follow-through and care.

Most Sidekicks land their first client within a week of finishing Academy, and fill their hours within a month.

Sidekicks keep roughly 70% of every monthly payment, and you can see what that looks like for you on our earnings card. 30% of the clients’ fees are retained by Sidekick (Pty) Ltd. We’ve invested millions of rands into the systems and people that handle sales, client matching, contracting, invoicing, billing, customer support, Sidekick Academy, customer success and most importantly, continuous support for you.

We doubt it. AI can draft an email. It can’t take a client’s car in for a service, or own a problem until it’s properly solved. We train every Sidekick to use AI well, to make you better and faster, not replaceable.

It depends on your experience and your clients’ needs. Here’s what Sidekicks earn, and how pay works.

See Earn well →
See all FAQs

Ready to join us?

Browse our open roles and apply. Don’t see the right fit, but know deep in your soul that you’re a Sidekick? Apply anyway and we’ll contact you when the perfect match comes up.

Open roles Apply anyway