About The Role

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 themPlanning 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 needsBeing 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 sagaKeeping the finances from becoming a shoebox of receipts and good intentionsTaking their car in for a service before they knew it was dueCompleting 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 replyingBooking and wrangling a high volume of calls and meetings before they wrangle your client's diaryFixing calendar sync issues across platforms (Google, Outlook) so nothing gets missedTurning chaotic notes, voice memos and meeting notes into neatly-organised and actionable projects & tasksBuilding and maintaining the systems, standard operating procedures, meeting rhythms and information that keeps everything organised and everyone saneGetting password and access management properly locked down across a teamKeeping the money stuff moving - invoices, receipts, expenses, and the bookkeeping your client has been 'about to do' for three monthsBuilding team culture and celebrating people - birthdays, all-hands, year-end functions, the moments that matterManaging socials so your client has a presence without it consuming their existenceCreating 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 workingPlanning the work trip down to the last detail. Flights, hotels, transfers, restaurants, and the backup plan when something inevitably goes wrong. Who you areGenuinely love helping others, solving their problems, and being willing to go the extra mile to bring joy and order to their livesProcess-driven and analytical, you'd rather follow (and improve) a good system than freestyleExtremely reliable and trustworthyCurious, open-minded, humble, and actively seek feedback to continuously grow and improveHighly organised, thorough and a detail-oriented perfectionistA great communicator who expertly manages expectations and creates clarityPositive, enthusiastic, uplifting energyBuilds strong, professional relationships with clientsProactive and takes initiativeWillingness to run errands and find joy in the mundane tasks RequirementsFluent in EnglishBased in or able to reliably commute to Cape TownValid driver's license and your own carTech-savvy and enjoy adopting new tools (e.g. Claude, Notion, etc.) Compensation, application process & other FAQsPlease 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!