The Todd Group is a family-owned landscape design, build, and maintenance firm with over four decades of experience delivering premium outdoor environments. Together with our sister company, Peters–Todd’s Inc., tree care and plant health care solutions.  LandBox LLC (LandBox Design Studio) is our in-house design studio creating a single source solution. Our companies thrive on craftsmanship, accountability, and teamwork, values that have guided us since day one.

This is not a traditional assistant role. This is an Operator EA position – part execution partner, part billing/admin quarterback, part internal communications hub.

Your mission is simple: increase CEO bandwidth and reduce chaos by:

owning the CEO’s workflow and initiative “buckets,”

driving follow-through across department leads,

supporting month-end billing and collection management,

handling executive communications,

personal support,

keeping executive systems clean (Dynamics dashboards, trackers, reporting cadence).

This role touches confidential financial, HR, and client matters – discretion and maturity are mandatory.

1. CEO Workflow, Priorities, and Accountability (Operator Core)

Build and maintain the CEO “Control Center” (tracker) for all initiatives, follow-ups, decisions, and deadlines.

Run a weekly cadence with the CEO: priorities, blockers, decisions needed, upcoming deadlines.

Protect CEO focus time and enforce calendar discipline (no agenda, no meeting; right people, right outcome).

Convert meetings into action: document decisions, assign owners, set due dates, and manage completion.

2. Month-End Billing Support (Unload the Weight)

You will become the quarterback for getting billing out the door.

Coordinate with Accounting and department leaders to gather job status updates, time and material work orders, change orders, and supporting backup needed for billing.

Track month-end billing readiness by department (Production, Maintenance, Tree Care/PHC, Irrigation/Lighting, etc.).

Ensure invoice timing aligns with internal deadlines.

Catch “billing leaks” early (missing documentation, unclear scope, unapproved changes).

3. Executive Email + Communications Management (Business + Personal)

Triage and manage CEO inbox(es): flag urgent, route/delegate, draft responses in CEO voice.

Maintain a simple response system: client follow-ups, vendor replies, internal

Draft key internal communications to department leaders and managers on behalf of the CEO.

Keep communication short, clear, and outcome-driven.

4. Executive Accounting & Admin Support

Support basic executive-level accounting coordination: approvals, expense routing, receipt capture, documentation requests, signature packages.

Organize and route documents between CEO and Accounting and relevant teams.

Assist with client billing communications and package presentation as needed.

Maintain clean file structure and standardized templates

5. Special Projects & Strategic Initiatives (TTG/PT/LandBox)

Execute special initiatives led by the CEO (process rollouts, new systems, team cadence, service offerings).

Build simple project plans and timelines; track progress; escalate roadblocks fast.

Coordinate cross-company initiatives that affect TTG, PT, and LandBox.

6. Department Lead Updates & Weekly Rhythm

Proactively collect updates from department heads and translate them into a concise executive summary:

Wins

Risks/Issues

Decisions needed from CEO

Next milestones

Run follow-up loops to ensure commitments are met.

7. Dynamics Dashboard Ownership (Once Built)

Maintain and refresh the Dynamics Sales Hub dashboard once created: pipeline hygiene, task follow-ups, reminders, dashboard accuracy.

Ensure consistent data entry habits across the team (light policing + training).

Provide CEO with a weekly dashboard snapshot: pipeline changes, stuck deals, next actions.

8. People Operations (HR.  Support — Coordination & Follow-Through

Coordinate recruiting logistics: postings, candidate scheduling, interview coordination, and hiring pipeline tracking.

Manage onboarding logistics and ensure all new hires complete required paperwork, system access, and role-ready setup

Maintain HR administrative records and compliance trackers (licenses/certifications, training completions, acknowledgements).

Coordinate PTO/attendance workflows and provide weekly visibility to leadership.

Support performance cadence: schedule reviews, track coaching plans/PIPs, and maintain documentation trackers for timely completion.

Coordinate safety training schedules and track compliance completion by department.

Handle sensitive employee information with discretion and professionalism.

Microsoft 365 (Outlook, Teams, Word, Excel, SharePoint/OneDrive, Planner)

Dynamics 365 Sales Hub (dashboard hygiene + follow-up cadence)

Sage 300 CRE formerly Timberline (billing support coordination with accounting)

ArborGold (PT operations awareness helpful)

Within 90 days, success looks like:

Month-end billing is organized, predictable, and on-time with fewer missing-backup scrambles.

CEO has a reliable “control center” with dramatically fewer dropped balls.

Department leaders provide updates in a consistent format; follow-ups are routine and effective.

CEO inbox is under control (triaged daily; drafts prepared; response time improves).

Dynamics dashboard hygiene is maintained, and the CEO can trust what it’s showing.

Must-Have

3–7+ years in EA / operations coordination / billing admin / project coordination.

Strong follow-through: you track, chase, and close.

Comfortable holding peers and managers accountable respectfully.

Strong writing skills and computer skills.

High discretion and professionalism.

Able to juggle multiple departments and shifting priorities without getting rattled.

Strongly Preferred

Experience in construction, trades, landscaping, home services, or project-based billing environments.

Familiarity supporting month-end billing.

Comfort learning CRMs and enforcing system hygiene (Dynamics, etc.).

Working Style Expectations (Important)

You’re proactive: you don’t wait for instructions when something is obviously slipping.

You bring solutions: when you escalate, you bring options.

You prefer clarity and order: you build systems and keep them alive.

You can handle direct communication and fast days.

Salary: $65k-75k (based on experience) + Bonus potential

Benefits: PTO, holidays, health, 401k

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