Administrative Support Specialist

About us

Pain in the Assistant is a team\-based administrative support and digital organization agency serving entrepreneurs and professionals across industries — coaching, legal, finance, real estate, entertainment, healthcare, and beyond. Founded in 2021, PITA takes a software\-agnostic, human\-centered approach to the work that keeps businesses running. We've saved thousands of hours for corporate executives and passionate founders at every stage of their journey, building systems that actually match how people think, work, and grow. We are not afraid of AI or any tool that helps us serve our clients better — and we will never mistake speed for humanity. Good people helping good people.

As a certified LGBT\-led organization, we take pride in continuing to cultivate a space that prioritizes listening and growth and that is safe and accepting of individuals from all backgrounds.

Overview

Hours are flexible, and the position would begin at 10\-15 hours per week with significant room for increasing hours upon proof of capabilities.

We want to make this role the right fit for you, and are looking for individuals interested in contract\-to\-hire for 3\-6 months before assessing part\-time or full\-time employment.

Your Responsibilities

Support operations directly related to our organization while supporting administrative tasks on behalf of our clients, such as:

• Sort and triage email inboxes including responding, organizing, and tracking all correspondence in Google Mail (Gmail) and Microsoft Outlook;
• Schedule and prepare for meetings;
• Schedule meetings by email and phone, and manage calendar appointments using Calendly and Google Calendar;
• Manage tasks in Asana;
• Prepare and maintain spreadsheets, documents, and databases in Microsoft Office, in Google Docs and Sheets, and in Notion;
• Book travel and other professional and personal reservations;
• Maintain confidential and sensitive information;
• Design and create presentations in Powerpoint and in Canva;
• Assist with research and development tasks and projects, and be prepared to make recommendations as necessary;
• Transcribe audio clips using Descript, and document key takeaways, next steps, and action items;
• Email and communicate occasionally on behalf of supervisor(s) and clients;
• Maintain and track progress of tasks and projects, ensuring that deadlines are not missed;
• Revise and send contracts and invoices, and track receipts of payment;
• Document processes and standard operating procedures, and revise processes as necessary;
• Manage client and team onboarding and offboarding processes;
• Perform clerical tasks such as data entry, bookkeeping, and record keeping;
• Maintain CRM records in Honeybook and Notion, or other comparable software;
• Create and edit social media graphics, photos, and content, and manage posting schedules;
• Copy write marketing materials, track asset usage, and strategize campaigns based on what is trending and Search Engine Optimization (SEO) keywords;
• Website management in WordPress using Wix, coordinating and managing blog content.

Who You Are

As applicants are expected to report directly to the founder with responsibilities ranging across departments, this position would be a great fit for someone interested in business ownership, personal branding, and connecting in entrepreneurial spaces.

You might be our ideal new hire if you:

(NOTE: Not everything below needs to resonate with you!)

• Find cleaning, organizing, or tidying tasks enjoyable or even fun;
• Create solutions and step\-by\-step guides on how to accomplish tasks, and review and update these processes regularly;
• Navigate inbox, calendar, and document management with advanced computer literacy;
• Bring certain “random” skills to your professional life;
• Envision and implement designs with an eye for creativity;
• Perform tasks with punctuality, simplicity, and a precise attention to detail;
• Maintain confidentiality and handle sensitive information with discretion;
• Ability to manage multiple tasks and projects;
• Enjoy collaboration but can work independently;
• Have experience with remote workplaces;
• Prove your proficiency in software such as Asana, Canva, Quickbooks and Freshbooks, Google Workspace and Microsoft 365, Honeybook, and other comparable tools;
• Offer experience as an assistant in any previous or current professional capacity.

Access to transportation is not necessary as this position is fully remote; you are expected to furnish your own working and functionally efficient computer device for employment. We do ask that you have a bachelor's degree or equivalent.

Please note: Any forms of discrimination, hate\-speech, racism, misogyny, queerphobia, or threatening of safety or security will not be tolerated under any circumstances and are subject for immediate termination.

Job Types: Contract, Temp\-to\-hire

Pay: $18\.00 \- $20\.00 per hour

Benefits:

• Flexible schedule
• Professional development assistance
• Referral program

People with a criminal record are encouraged to apply

Application Question(s):

• Please note: Any forms of discrimination, hate\-speech, racism, misogyny, queerphobia, or threatening of safety or security will not be tolerated under any circumstances and are subject for immediate termination. Please respond "YES" below to confirm you have read and agree to these terms.
• The current hourly rate for this role is $18\-20/hr. Please confirm below that you understand and agree to this rate.
• Tell me more! Is there any other information or context you can offer that will help me better prepare for our time together?

Location:

• United States (Required)

Work Location: Remote