Sidekick (Personal/Executive Assistant) | Pretoria
About Sidekick
We help Founders, CEO's, Directors (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.
See our website for more info:
The Role As a Sidekick...
We're currently looking for Sidekicks based in or around Pretoria who thrive in fast-paced, high-agency environments, and who are process-driven, for hybrid part-time or full-time client support. No two days look the same, and that's exactly why this role suits people who are organised, adaptable and energised by variety. You'll be matched with a client(s) whose needs align with your skills and experience. Over time, many Sidekicks grow into indispensable partners in their clients' lives.
Personal Assistance
Depending on your client(s), you might be helping with:
Supporting home errands and small renovation or repair projects as they come up
Being the person who anticipates your client's personal needs and general life admin as the relationship grows
Picking up the household load that currently falls on a partner or spouse
Meal planning and grocery list coordination
Being the main point of contact for all of your clients needs
Business Assistance
Or on the professional side, you could be working on things like:
Taming the inbox that multiplies like rabbits, especially when your client is travelling or heads-down - triaging, drafting, flagging what needs a response
Post-meeting follow-up, note-taking and task capture, working alongside whatever meeting-notes and project-management tools your client already uses
Liaising on your client's behalf with skilled communication
Logistics support during busy weeks - picking things up, coordinating with a stretched team, being a point of contact
Being polished and professional enough to represent your client when the need arises
Who you are
Confident and able to run with a clear instruction without needing to be micromanaged
Honest and upfront, someone who owns mistakes rather than covering them up
A strong two-way communicator
Genuinely love helping others and willing to go the extra mile
Curious, humble, and actively seek feedback to grow
Positive, proactive energy, and find joy in the mundane tasks
Requirements
Fluent in English
Own Laptop + Fast & Reliable WiFi
Based in or able to reliably commute to Pretoria
Valid driver's license and your own car
Tech-savvy and enjoy adopting new tools (e.g. Claude, Notion, etc.)
A bonus if you have some background in production, media or project management, though attitude and adaptability matter more than industry experience
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!
PS. A quick note on "full-time": this isn't a permanent employment role. Like most Sidekicks, you'll work as an independent contractor, and we'll match you with several clients to fill your week (for example, four clients at 10 hours each for a 40-hour week). If a client ever ends their engagement, which is rare, they're required to give one month's notice, and we'll work to match you with a new client in that time.
Skills
As published by ashby · 22 questions · 12 written answers
Basics
Let's start with the easy stuff. What's your first and last name?, Email, Please upload your CV
Short answers (6)
- What's your Whatsapp number? (I'll use this to contact you about the application process, and promise not to sell your number to a funeral insurance company)
- Let's have an honest conversation about earnings. optional
- Link to your LinkedIn profile
- What's your address? Please include your suburb, city and country.
- When would you be available to start working as a Sidekick?
- For each manager listed above, do we have your permission to contact them for a reference check?
Pick from a list (4)
- Do you have your own car and valid driver's license?
- Which formats of work are you open to?
- Which of the following do you have experience in?
- Do you have your own laptop and fast wifi? optional
Written answers (12)
- Give me the headline version of you - who you are, what you love doing outside of work, and a pet peeve. optional
- Tell me about a gift or act of kindness for a friend/stranger that you’re proud of optional
- Are you looking for full-time or part-time work? How many hours per week are you available? Do you have any time constraints (e.g. can only work from 9am to 1pm because you're parenting)? *Note: we ideally want candidates who are keen to fill 30 to 40 hours per week with Sidekick work. In some cases, we have candidates who start with only 15 hours available, but then move towards 30-40 hours.
- Have a read of "How much will I get paid?" on our Careers page. Does that work for you? Tell us why or why not.
- Tell me about your career story. Where have you worked in the past? What type of work do you love vs hate? optional
- I'm sure you're normally humble. But for one moment, take your humility hat off. Why do you think you’ll be an incredible Sidekick? What experiences and achievements would you like to share? optional
- What position do you currently hold? What are the push and pull factors influencing your next career move? optional
- If you could invite 3 famous people for dinner (dead or alive), who would you invite and why? optional
- Please list your current manager (if applicable) and your previous two managers. If you do not currently have a manager, please list your previous three managers. For each, provide their full name, job title/relationship to you, email address, and contact number.
- For each manager you've worked with, briefly note the strengths and development opportunities they would highlight in your performance optional
- How did you hear about Sidekick and this opportunity? Please be as specific as possible (e.g. name the person, describe the Linkedin post) optional
- Any final comments or questions for me?:) optional