Now Hiring: Executive Assistant and Operations Coordinator

About This Role

I'm the founder and operator of three interconnected, but separate businesses: With Grace Coaching & Consulting (executive coaching and organizational development), Retreat Inward (luxury leadership retreats), and Coaching for Community Leaders (a 501(c)(3) nonprofit). I need someone who can support me in getting things done for With Grace and Retreat Inward—helping me bridge my strategy to the tactical work that keeps my businesses running while I focus on service delivery and development, strategic direction, and growth. My nonprofit (C4CL) has separate support, but you'll maintain visibility into the elements that affect my priorities and schedule.

This is a hands-on role that blends project management and executive support. You'll be managing client projects in Asana, drafting contracts, preparing workshop materials, coordinating schedules, executing marketing tasks, and handling the day-to-day operations that make everything work, while keeping an eye on support and capacity-building for me. 

A note on fit: My work centers on leaders who are often the 'only'—trailblazers whether by choice or lack of representation, and the 'other'—outsiders whose belonging is questioned or excluded by systemic design. I am committed to expanding who gets access to leadership development and potential-maximizing services I provide and supporting people in leading effectively and authentically—not despite who they are, but because of it. These values directly shape how I operate and grow my businesses, who I serve, and the kinds of teams I build. I'm looking for someone who shares this orientation and is comfortable with how overtly these values show up in my work—this isn't background or silent context, it's front and center in how I talk about what I do, who I serve, and why it matters. If this does not resonate authentically with you, please do not apply to respect both of our time. 

How I Work

I'm someone who sees what's possible and makes it real—that's been true in many ways in my life, across my career, and in building these businesses. That ability comes from the capabilities I've developed, my experience and formal education—and is powerfully fueled by my neurodivergence. My neurodivergence primarily shows up in how I think, solve, and adapt rapidly and creatively, see not only the bigger picture but the myriad details and dependencies others usually miss, and naturally see the path from concept to creation.

I know myself well—both my capabilities and internal obstacles, and what I need to support my success. I'm an active processor who thinks out loud, and I do my best work when I have a thought partner who can help me clarify the details of how and when, and then take ownership of executing those details. As that pertains to this role, I need someone who can engage with me as I'm thinking, has a project management mindset to break things down early so we can identify what doesn't have to be me, and then run with their piece.

The structures for how we work together are already largely in place and documented after learning from and experiencing the kind of support I need to maximize my strengths in my work. I need someone with the capacity and initiative to step into them, while remaining open to how things may need to evolve along with my businesses. Additionally, the current incumbent for this position is committed to a healthy transition period and will provide on-the-job training in a timeline that works well for all of us. 

To support our working relationship, I'll ask you to take a DiSC assessment once you're onboard and share mine with you. I'll provide a debrief session so we can understand each other's communication styles, tendencies, and potential areas of friction—and how to proactively navigate them. The assessment results and online tool access are yours to keep, regardless of how long we work together.

What I Need From You

I need a partner, not an order-taker—someone with the emotional maturity to engage in direct, honest communication without personalizing feedback or overthinking what I say. I need to work with someone who takes me at face value or if something feels off about what I’m saying vs. doing – you’ll care for yourself by not wasting time/energy on assuming and also respect me enough to raise it for discussion. 

This role also requires someone who already has the personal systems and habits to stay organized, manage multiple priorities, and follow through without reminders or relying on others to motivate them. This is not the job where you'll finally become that person—I need someone who already is and is energized by the opportunity to flexibly and meaningfully apply their talents in this role. 

You must be a strong written communicator—clear, professional, and able to adapt tone for different contexts. You’ll also need to be comfortable working across multiple technology platforms, learning new systems quickly as needed and leveraging AI appropriately to increase efficiency and quality outcomes. 

Here's what that looks like in practice:

• Get things done without constant supervision. I'll provide direction on what needs to happen and when. I’ll rely on you to figure out how to make it happen, ask questions when you need input, and deliver. You must be comfortable engaging with me while I’m still working something through—not waiting for perfect instructions, but helping shape them in a way that enables your contributions and take ownership of your piece once we're aligned.

• Ask good questions. If something is unclear or you're not sure how I'd want it done, ask. Clarifying your understanding and checking in isn't “bothering me”—it's good communication and partnership.

• Receive feedback. Sometimes the way you do something won't be quite right, and I'll need to redirect. I need someone who can hear that, adjust, and move forward, instead of experiencing it as an indictment on their competence or value. Feedback is part of how we get better together.

• Pay attention to details. Formatting matters. Deadlines matter. Getting names and numbers right matters. I need someone who catches their own errors and takes pride in quality work.

• Care about the bigger picture. Even though the work is tactical, I need you to understand why it matters—and you can count on me to constantly equip you with context accordingly. When you know the context, you make better decisions about how to execute and can help identify where you can contribute more.

• Be reliable and consistent. I need to be able to count on you. That means meeting deadlines, communicating proactively if something is delayed, and showing up consistently.

Primary Responsibilities

Client Project Management (Core)

• Create and maintain client projects in Asana—setting up project structures, tracking deliverables, updating status

• Keep project records current so I always know where things stand

• Flag blocked or stalled work before it becomes a problem

• Prepare data and updates that support invoicing processes

• Coordinate with other subcontractors on project deliverables and status updates

Contract & Document Preparation (Core)

• Draft client contracts and engagement letters using templates and my input

• Prepare materials for workshops and presentations—slides, handouts, participant materials

• Track contracts through signature process and follow up as needed

• Maintain organized files and documentation

• Draft other communications/deliverables as requested

Calendar & Schedule Coordination (Core)

• Manage scheduling across all three businesses, including awareness of how my nonprofit commitments affect availability

• Coordinate meeting logistics—location, timing, participant communication

• Handle scheduling changes and communicate updates to relevant parties

• Over time, take on more scheduling decisions as you learn my preferences and constraints

Marketing Execution (Core)

• Create and maintain a content calendar based on marketing strategy I provide

• Execute consistent posting on LinkedIn and Instagram with content I provide (1-2x/week)

• Manage newsletter production and distribution

• Track and support engagement and flag what's working/not or requires my action

• Implement basic website updates as needed

Retreat Inward Support (Seasonal/Event-Driven)

• Coordinate logistics for local retreats and day events

• Manage participant communications and registrations

• Support marketing for offerings

• Provide logistics, participant management, and administrative support for larger events (ex: annual retreat in Hawai'i), but likely with the added support of a travel specialist in the future for larger destination retreats

Inbox & Communication Support (Light)

• Draft responses for my review when requested

• Track pending items (contracts awaiting signature, follow-ups needed) and manage follow-up

• Monitor cc'd communications and flag anything requiring action

Financial Operations Support (Light)

• Interface with my CFO regarding invoicing processes

• Prepare data and maintain records that support the invoicing cycle

• Keep projects updated that involve financial tracking

• (Note: You won't do bookkeeping or direct invoice creation—that's handled separately)

Personal/General Assistance (Light)

• Research and narrow down options for decisions (travel, services/service providers, vendors, purchases)

• Make dinner reservations and similar bookings

Systems We Use

• Asana — project and task management

• Google Workspace — email, calendar, docs, sheets

• Calendly — scheduling

• Mailchimp — email marketing

• Squarespace — website management

What Success Looks Like

In the first 3 months:

• You're fully familiar with our routines and handling core responsibilities more independently—client project management, contracts and documents, scheduling, and marketing execution

• You're building experience with the other areas (retreat support, financial operations) and know when to check in vs. move forward

• You've started identifying gaps in our processes or systems—places where things are clunky, unclear, or could work better—and we're beginning to discuss and prioritize improvement opportunities together

• Process documentation is current and reliable

• Your work is getting done on time and done well, AND you're helping me stay on track, following up when you're waiting on my input and holding me accountable to deadlines we've set together, instead of the other way around

In 6 months:

• We've implemented improvements in core areas and solidified how we work together

• We're in a genuine rhythm—you can anticipate what's coming and I can trust that things are handled

• You're starting to apply your strengths more strategically as you've learned more about me, my preferences, and my businesses

• We're looking at the year ahead together, bringing structure to my strategic direction and planning how your support will evolve

• Your compensation rate has increased to reflect the tangible value you're bringing

The bigger picture:

• My time and capacity have grown—I'm spending less energy on operations and more on clients, programming, and future direction

• We've optimized current operations while building flexibility for how my businesses will grow and change

• You're not just keeping things running; you're helping me stay ahead of what's coming and what I want to create

Schedule & Availability

• Weekly sync: We'll meet for approximately 1 hour each week to align on priorities. Mondays between 9am-1pm EST work best given the nature of the work cycle, but there's flexibility to adjust when needed.

• Other meetings: Flexible within normal business hours, as-needed. It’s likely we’ll have more as you get up to speed and to support seasonal/kick-off types of efforts as they arise, and wane as we get into a routine.

• Availability: Much of this work can be planned and scheduled in advance, but some coordination happens in real time—especially around scheduling, client communications, and task handoffs. Because my client work operates on East Coast business hours, you'll need overlap with that window most weekdays so we can collaborate when needed and you can act on time-sensitive requests without significant delay. This doesn't mean being on-call or having set hours, but it does mean I can generally expect you to be available most days of the week—either to respond within the same or next business day, or to coordinate with me on adjusting priorities to accommodate something new that needs attention.

• Time off: Just communicate in advance when possible so we can plan accordingly.

Compensation & Growth

• Hours: 15-20 hours/week 

• Compensation: $30-35/hour to start (1099 contractor), with a minimum 10% rate increase at the 6-month mark based on performance aligned with the success factors described above.

• Start: Ideally early March 2026, with transition support from current incumbent provided.

• Growth potential: There is real opportunity for this role to grow—either expanding toward full-time hours or evolving into a more senior position as my businesses develop. I can also envision splitting this into two roles in the future. At the same time, you have no requirement to grow nor do I make any promises—all of this will depend on business needs, how we work together, and your ambitions. I care about and invest in the people I work with and genuinely want to see them develop their fullest potential, and I’m always happy to provide those opportunities where I can or supporting them in finding that path for themselves.