Executive Assistant (EA) at UpSkill… at EF Specialists · San…

About the Company 

UpSkill Specialists, LLC is an adult executive function coaching company that supports neurodivergent adults, professionals, students, and organizations in building executive function skills through personalized, 1:1 virtual coaching. Their approach focuses on practical strategies and ongoing accountability to help clients improve daily functioning, independence, and success in work and life. We serve clients nationwide, with all sessions conducted remotely.

The company was founded by Eric Kaufmann and Sean G. McCormick in 2023 and is based in California. Both founders come from a background in education, special education, executive function coaching, and educational therapy, and have run their own coaching companies.

Position Overview

The Executive Assistant (EA) at UpSkill Specialists serves as a strategic partner to the CEO and lead coaches, managing high-level administrative operations, complex calendars, marketing, and client communications to support business growth. This role oversees program logistics, facilitates client intake, coordinates training, and acts as a gatekeeper—ensuring leadership can stay focused on content delivery and strategic priorities.

This individual functions as a trusted right-hand, managing day-to-day operations, protecting executive time, maintaining internal systems, and ensuring clear, consistent communication across coaches, clients, contractors, and professional partners.

This role reports directly to the founder. It is a part-time, hourly employee position, requiring approximately 5–15 hours per week.

Ideal Candidate

The ideal candidate thrives in a fast-paced environment, anticipates needs before they arise, and is equally comfortable managing logistics, refining systems, and handling sensitive information with discretion. They are self-motivated, able to work with minimal supervision, and capable of managing a flexible schedule.

We are looking for an organized problem-solver who is passionate about supporting the company, its clients, partners, and staff through thoughtful collaboration and high-quality service.

Key Responsibilities

• Manage complex calendars, scheduling, and prioritization of meetings and commitments
• Serve as the primary point of contact for internal and external communications
• Coordinate client intake, onboarding, and ongoing communication
• Oversee program logistics, including scheduling sessions, tracking engagement, and ensuring smooth service delivery
• Assist with marketing and materials that include: blog posts, newsletters, presentations, and website content.
• Prepare, organize, and maintain documents, reports, and internal systems
• Support training coordination, team meetings, and internal operations
• Act as a gatekeeper by prioritizing requests and protecting executive time
• Maintain and improve operational systems and workflows for efficiency
• Liaise with coaches, clients, contractors, and professional partners to ensure clear communication
• Act as the primary point of contact between the CEO, staff, clients, and contractors
• Ensure timely follow-up on internal and external requests
• Handle travel and booking logistics as requested
• Handle sensitive information with a high level of discretion and professionalism
• Support continuous improvement of systems and documentation
• Assist with special projects and strategic initiatives as needed
• Other tasks as requested by Leadership

Requirements, Skills & Qualifications

• Must reside in California
• Able to provide professional references within the field
• Must be able to pass a background check and fingerprinting (California requirements)
• Available to meet weekly via Zoom with the founder during normal business hours
• Able to manage a flexible schedule and prioritize responsibilities independently
• Comfortable working with minimal supervision while maintaining strong accountability
• Have a dedicated quiet space to hold meetings with leadership, clients, staff, and partners
• Computer (Mac or PC) for daily work and having remote meetings
• Have a smartphone for communication and texting
  

Core Skills & Competencies

• Highly organized, detail-oriented, and able to manage multiple moving parts
• Proactive problem-solver with the ability to anticipate needs before they arise
• Strong prioritization and time-management skills
• Clear and professional communicator (written and verbal) with excellent follow-through
• High level of discretion and ability to handle confidential information
• Adaptable and able to thrive in a fast-paced environment
• Systems thinker with the ability to improve and maintain workflows
  

Technical Skills, Apps, and Software

• Google Workspace (Gmail, Google Calendar, Docs, Sheets, Drive)
• Microsoft Office (Excel, Word, PowerPoint)
• Zoom, Google Meet, and Team
  
• Instagram, TikTok, LinkedIn (basic familiarity)
  
• Comfortable learning and using new platforms such as: 
•  GoHighLevel and Notion
  
• Wix (blog formatting and SEO settings)
• Notion
• CRM systems, Tutorbird
  

Key Expectations by 60 Days

• Complete all onboarding and orientation tasks
• Meet weekly with the founder for guidance, feedback, and ongoing support
• Collaborate with the founder to develop a role-specific playbook, including SOPs, templates, checklists, and workflows to support scalability
• Gain proficiency in GoHighLevel to support sales, client intake, scheduling, and data tracking

- Establish a Consistent Operating Rhythm

• Maintain weekly internal check-ins
• Take ownership of calendar and inbox management, including prioritizing communications, resolving scheduling conflicts, and managing shifting priorities

- Growth in the Role

• Transition from reactive task execution to proactive support by anticipating needs, suggesting solutions, and initiating actions
• Begin identifying and recommending process improvements to streamline workflows and enhance operations
• Build strong working relationships with the founder, coaches, clients, and key stakeholders
• Demonstrate increasing ownership of high-level responsibilities, such as coordinating travel, planning meetings, and supporting strategic initiatives

How to Apply

Apply online through Bamboo HR. Please submit the following materials: 

1. Resume, Cover letter, LinkedIn Profile, and any certifications
2. Professional references (3)
3. Why you would be a good fit for this role
4. Availability 

• Your current availability (estimated hours per week)
• Available to start date