Position Description: Executive and Personal Assistant to CEO - With Grace LLC  

Position Type: Independent contractor (1099)

Schedule: Part-time, almost all responsibilities can be completed asynchronously/at any time of day. There will be approximately 5 hours/week initially, with potential for more based on candidate’s abilities and preferences. The position is available immediately.

Location: Remote with some in-person opportunities local to the DMV area (primarily Howard County, MD)

Pay Range: starting at $25/hour 

About Us: With Grace LLC is a growing executive coaching and consulting company specializing in leadership development for those who consider themselves to be the “Only,” a trailblazer by choice or lack of representation, and the “Other,” an outsider whose belonging is questioned internally and/or externally face additional challenges. The With Grace philosophy centers on helping clients achieve success and fulfillment because of their unique differences rather than in spite of them. Services range from one-on-one coaching sessions, in-person and virtual group facilitation, workforce consulting and solution delivery, and bespoke training, workshop, and keynote speaking engagements. 

The Retreat Inward is a growing business venture of With Grace LLC that provides transformative self-leadership retreat experiences in partnership with a creative collaborator. Over the next year, this venture will become an increasingly significant aspect of the Executive Assistant’s responsibilities. 

There is a wonderful incumbent in this position who is still providing support for key responsibilities until a new candidate is in place and trained by the incumbent.

Personal Attributes Required:

I strongly believe that our interpersonal chemistry and alignment of values is going to make or break the value of working together. As such, the below list of your personal attributes will be the most important aspect of initial vetting. If this list is describing you or how you sincerely endeavor to achieve, please keep reading!

Self-Awareness as evidenced by your clear understanding of your own needs and responsibilities, what your strength and growth areas are, and the growth you have fostered in yourself as a result. 

Direct Communication as evidenced by your ability to express your needs and concerns clearly and professionally, your ability to have difficult conversations effectively, and comfort with giving and receiving direct feedback. 

Emotional and Interpersonal Maturity as evidenced by your ownership of managing your own emotional responses, lack of expectation for others to intuit on their behalf, and maintaining appropriate professional boundaries. 

Personal Agency as evidenced by your consistent initiative in problem-solving and solution-building vs. just highlighting or accepting problems, proactively managing your own role and responsibilities in all areas of your life, and discernment in knowing when/how to handle issues independently or need to escalate and ask for support. 

Primary Responsibilities:

Executive Support

• Manage CEO's calendar, scheduling, and coordination with clients and team members

• Manage CEO's inbox, including email prioritization, organization, and proactive handling of routine correspondence

• Monitor and respond to emails within scope of authority

• Maintain organized email filing system and flag urgent matters requiring CEO attention

• Maintain organized systems for virtual filing and document management

• Process and review invoices, reconcile accounts receivable

• Format and proofread documents and deliverables

• Create first drafts of presentation materials

• Research and report on requests from CEO (i.e. vendors, products, solutions, etc)

• Maintain and create documented processes for key/routine business activities

• Provide support for CEO’s personal/family requirements such as creating and maintaining family schedule templates, researching camps or activities options for her children, researching and/or booking personal travel, scheduling appointments or reservations, researching/coordinating vendors, services, and/or other requests to support reducing CEO’s administrative burden  

• Negotiable: run local errands/returns 

Client & Project Management

• Update and maintain client status tracking in Asana

• Prepare client status summaries and project updates

• Coordinate with contractors and team members

• Monitor project timelines and deliverables

• Ensure all systems are updated at least a couple times a week

Retreat Program Support

• Serve as Retreat Concierge for attendees, managing registration and communication

• Track attendee progress and provide support throughout their pre/post retreat journey

• Assist with travel arrangements as needed

• Research and evaluate potential retreat locations

• Support retreat planning and event coordination

Ideal Skills & Qualities:

• Exceptional organizational and time management skills

• Strong attention to detail and ability to maintain accurate records

• Proficiency with project management tools (specifically Asana)

• Experience with or ability to learn basic accounting/bookkeeping tasks

• Professional demeanor and strong client service orientation that is effectively conveyed in both written and verbal communication via tone, spelling, and grammar  

• Self-motivated, proactive, and works independently

• Previous assistant/administrative experience

• Background or desire to support event planning/coordination

• Experience with social media management

• Familiarity with coaching/consulting industry

Training & Support:

• Comprehensive training to be provided by current virtual assistant

• Regular bi-weekly meetings with CEO

• Additional support available from the CEO as needed

Growth Opportunity:

• Potential for increased hours and  more complex and strategic projects in accordance with the Executive Assistant’s interests, availability, and capabilities

• While all work can be completed remotely, there will be opportunities based on the candidate’s preferences to occasionally provide support for in-person meetings/engagements or other tasks/actions that may require local travel

Technology Requirements:

• Reliable internet connection 

• Password protected profile on computer/laptop (non-mobile computing device required for certain responsibilities) to ensure data integrity and confidentiality of With Grace client and financial information  

• Proficiency in standard business software (Microsoft, Google Workspace) 

• Ability to learn and adapt to new digital tools