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: www.sidekick.cool

 

The Role As a Sidekick...

You'll work full or part-time with one or more clients, supporting them across their personal and professional lives. 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 clients whose needs align with your skills and experience. Over time, many Sidekicks grow into indispensable partners in their clients' lives.

 

We're currently looking for Sidekicks based in or around Cape Town who thrive in fast-paced, high-agency environments, and who are process-driven, for hybrid client support.

 

Personal Assistance Depending on your client, you might be helping with:

• Calendar ping pong and wrangling someone's schedule before it wrangles them

• Planning an epic overseas trip (that doesn't involve a 14-hour layover in Dubai)

• Finding birthday gifts that are thoughtful, on time (and not a regift of your granny's bath soaps)

• Planning & organising meals that are thoughtfully curated to your clients needs

• Being the person who anticipates your clients personal needs like, booking doctor's appointments, scheduling that overdue eye test, and more.

• Decoding a medical aid claim before it becomes a 6-month saga

• Keeping the finances from becoming a shoebox of receipts and good intentions

• Taking their car in for a service before they knew it was due

• Completing tedious paperwork for applications and being the main point of contact for your client

 

Business Assistance or on the professional side, you could be working on things like:

• Taming the inbox that multiplies like rabbits - triaging, drafting, unsubscribing, actually replying

• Booking and wrangling a high volume of calls and meetings before they wrangle your client's diary

• Fixing calendar sync issues across platforms (Google, Outlook) so nothing gets missed

• Turning chaotic notes, voice memos and meeting notes into neatly-organised and actionable projects & tasks

• Building and maintaining the systems, standard operating procedures, meeting rhythms and information that keeps everything organised and everyone sane

• Getting password and access management properly locked down across a team

• Keeping the money stuff moving - invoices, receipts, expenses, and the bookkeeping your client has been 'about to do' for three months

• Building team culture and celebrating people - birthdays, all-hands, year-end functions, the moments that matter

• Managing socials so your client has a presence without it consuming their existence

• Creating the deep-dive research docs, slide decks, and spreadsheets your client keeps bumping to 'when things are quieter' (they won't be)

• Keeping the office running - supplies, lunches, deliveries, cleaners, visitors, the stuff nobody notices until it stops working

• Planning the work trip down to the last detail. Flights, hotels, transfers, restaurants, and the backup plan when something inevitably goes wrong.

 

Who you are

• Genuinely love helping others, solving their problems, and being willing to go the extra mile to bring joy and order to their lives

• Process-driven and analytical, you'd rather follow (and improve) a good system than freestyle

• Extremely reliable and trustworthy

• Curious, open-minded, humble, and actively seek feedback to continuously grow and improve

• Highly organised, thorough and a detail-oriented perfectionist

• A great communicator who expertly manages expectations and creates clarity

• Positive, enthusiastic, uplifting energy

• Builds strong, professional relationships with clients

• Proactive and takes initiative

• Willingness to run errands and find joy in the mundane tasks

 

Requirements

• Fluent in English

• Based in or able to reliably commute to Cape Town

• Valid driver's license and your own car

• Tech-savvy and enjoy adopting new tools (e.g. Claude, Notion, etc.)

 

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!