Lead Administrator & Executive Assistant

Job Description

Job Description

Lead Administrator & Executive Assistant

Supporting Central Operations for a Family of Small Businesses (Aviation, Engineering, Technical, Skilled & Artisan Trades)

Contracts • Finance/Bookkeeping • Regulatory Filings • HR • Executive Ops • AI-First Systems

Overview

We build businesses that serve people. This role turns vision into motion—contracts signed, books reconciled, great people hired and onboarded, filings on time, leaders supported. Administration here is leadership: you create order out of noise, move work to done, and raise the standard while you do it.

On any given day you’ll face more pull than one person can finish. You will think, decide, and deliver: reduce thirty-five competing requests to the vital seven, set clear commitments for the rest, and ship accurate, on-time outcomes under pressure. You design simple systems, communicate crisply, use AI as a power tool (never a crutch), and know when to move fast and when to slow down to get it right.

If you’re energized by ownership, service, and results—and ready to invest yourself in meaningful work alongside high-performing teammates—you’ll thrive here. If you’re guarding hours, chasing “good enough,” or looking for a lifestyle desk, you won’t. We honor real family commitments and expect adults who keep their word.

Our Core Values

At the heart of our organization are three core values that guide everything we do—from daily tasks to long-term strategy. These values are not just ideals; they are behaviors we expect, reward, and live by across all companies in our network.

Excellence

We pursue excellence with confidence and humility—owning our work, communicating effectively, and refusing to compromise on quality. We believe true excellence blends technical skill with continuous learning, personal responsibility, and a team-first mindset.

Compassion (Others-First Service)

Our approach to compassion is action-oriented. We lead with empathy, selflessness, and teamwork—putting the needs of others first while maintaining high expectations. It’s about serving with care, offering support, and creating a positive impact—without enabling excuses or compromising accountability.

Purpose (You Were Made for This)

We believe each person was created for a purpose—and that includes their work. The best administrators don’t just organize calendars or run reports—they bring clarity, calm, and forward motion to everyone around them. They know why they do what they do, and they choose to serve others through their unique blend of insight, drive, detailed organization, and excellence.

If you’re someone who sees administration as more than a job—if it’s the work you were made to do—we want to hear your story. Show us how your sense of purpose aligns with this opportunity to lead, serve, and make an impact.

What You’ll Do

Central Administration

• Keep shared work flowing across companies.
• Coordinate leaders/admins; clear blockers fast.
• Publish simple weekly status and risks.

Contracts

• Manage templates, routing, signatures, repository.
• Track renewals and vendor requirements.

Finance

• Run AP/AR, purchasing, reconciliations.
• Support month-end close and cash visibility.

Regulatory

• Keep entities compliant: filings, licenses, deadlines.
• Coordinate with tax/accounting partners.

Hiring & Onboarding

• Post, screen, schedule, offers, onboard, support.
• Standardize onboarding checklists and records.

Executive Operations

• Own calendars, travel, meeting prep/minutes.
• Drive follow-through on initiatives.

Prioritize & Deliver

• Triage vital actions; set dates for the rest (and achieve the dates)... a step at a time
• Protect focus blocks; finish what you start.

Systems & Automation

• Build clean SOPs and checklists.
• Use AI and simple automations to remove busywork.

Who You Are:

• Ownership & Grit — You take responsibility, keep your word, and push through to done.
• Focus & Finish — Cut noise to the vital work; set dates for the rest; close loops.
• Craftsmanship — Clean, accurate work; know when speed is right and when precision is required.
• Others-First Service — Anticipate needs, make teammates better, protect their focus.
• Clarity & Calm — Plain language, clear next steps, steady under pressure.
• Systems Mindset — Build repeatable ways of working; leave every process better.
• AI, Used Wisely — Power tool, not a crutch; verify sources and catch errors.
• Coachable & Direct — Seek feedback, speak plainly, own outcomes.
• Practical Track Record — Real results from work, school, trade, or serious projects—not theory.

Qualifications

Must-Haves

• Proven capability: Degree or clear evidence of outcomes (internships, startup, military, trade, major projects).

• Executive-grade communicator: Clear briefs, texts, and emails; frame options with pros/cons and risks; offer a recommendation; anticipate questions; bring facts—not “what do you want?”.

• Owned end-to-end work: You have personally done at least three of the following from start to finish: getting contracts signed and renewed; closing monthly books and doing reconciliations; submitting required filings on time; hiring and onboarding a new team member; running executive operations (calendar, travel, meeting prep and follow-up).

• Financial basics: AP/AR, reconciliations, cash tracking; build and follow a simple budget.

• Core tools: GPT (prompting + fact-checks), QuickBooks Online, spreadsheets (lookups, pivots), bill-pay/expense app, a task manager, a docs/wiki, a simple hiring tracker.

Strong Pluses

• Multi-entity operations experience.

• Regulated or aviation-adjacent work.

• Portfolio integration: You’ve helped integrate an acquired company—people, payroll, policies, contracts, accounts.

Not a Fit If

• You optimize for hours over outcomes; a strict 9–5 is your priority.

• You ask “What do you want?” instead of presenting options with a recommendation.

• You avoid owning mistakes or you soften/hide bad news.

• You try to do all 35 requests and finish none; prioritization is painful.

• You freeze under pressure or chase perfection instead of shipping.

• You consider “small” tasks beneath you when the mission requires them.

• You won’t write clear briefs—no options, risks, or next steps.

• You dislike documenting process and keeping simple SOPs current.

• You resist learning tools (GPT, spreadsheets, QuickBooks) to move faster.

• You need constant supervision and don’t set or renegotiate dates proactively.

• You view administration as clerical, not leadership and stewardship.

• You’re uncomfortable handling confidential info with strict discretion.