Senior Executive Assistant & Operations Coordinator

Job Description

AZIMUTH CONTRACTING, LLC

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SENIOR EXECUTIVE ASSISTANT & OPERATIONS COORDINATOR

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Westchester, Illinois | Full-Time | Salaried

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$80,000–$95,000 annually

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Are you the person others trust to keep things organized, follow through, and get important work finished?

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Azimuth Contracting, LLC is a veteran-owned facilities management and government-contracting company supporting healthcare operations, including facilities services, break-fix repairs, fire- and life-safety coordination, and construction-related work for veteran healthcare facilities.

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We're seeking a Senior Executive Assistant & Operations Coordinator to work directly with ownership as the administrative backbone of a growing company. Reporting to the COO and working closely with the CEO and field team, you'll organize priorities, build practical systems, manage follow-up, and personally execute important business-support work.

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This is a high-trust, hands-on, Westchester-based role for an experienced professional who can independently organize work, build systems, follow through, and personally complete important administrative and operational tasks.

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A SMALL-TEAM ROLE WITH REAL OWNERSHIP

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Azimuth is intentionally small and practical—not a large corporation with layers of departments and narrow job boundaries. You'll work directly with ownership, see how decisions become action, and understand how your work affects the company, field team, clients, and future growth.

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Our team consists of two owners, a field project manager, a field supervisor, managing roughly 10–20 projects per year. That lets us build practical, repeatable systems rather than bureaucracy.

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Some days involve paperwork, data entry, and document follow-up. Others involve preparing a purchase order, organizing subcontract paperwork, entering field records, or improving a Planner workflow. We need someone who enjoys the work, takes ownership, and makes the next occurrence easier.

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This is not a receptionist or people-management position—it's a senior, hands-on individual-contributor role with no direct reports. You'll personally prepare documents, build and maintain workflows, enter information, maintain records, follow up with others, and bring routine work to completion. Leadership retains final financial, contractual, and strategic decisions.

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WHAT YOU WILL DO

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Keep Tasks and Recurring Work Moving

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·       Use Microsoft Planner as the central record for priorities, deadlines, and follow-up.

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·       Turn emails, meetings, and field information into clear tasks with owners, due dates, and files.

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·       Build task lists so the team can pull work from an active system instead of verbal reminders.

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·       Track deadlines and blockers; raise issues early when leadership input is needed.

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·       Provide concise updates to ownership at key decision points.

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·       Use approved AI tools for task creation, summaries, and draft communications, reviewing all outputs for accuracy.

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Prepare Subcontract and Insurance Documentation

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·       Populate subcontract templates and attach scopes of work from leadership.

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·       Prepare contract-administration packages for review, routing, signature, and filing.

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·       Track outstanding signatures, certificates of insurance, endorsements, and waivers of subrogation.

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·       Follow up persistently with subcontractors and vendors on missing information.

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·       Maintain organized contract, vendor, and project-administration files.

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·       Escalate coverage questions or unresolved risks to the COO.

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Support QuickBooks and Routine Purchasing

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·       Prepare estimates, purchase orders, and invoices in QuickBooks per company procedure.

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·       Support booking transactions once approvals and documentation are complete.

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·       Coordinate orders for supplies, materials, and equipment; track deliveries and receipts.

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·       Occasionally process client credit-card payments by phone (about once monthly).

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·       Protect confidential financial information; ownership retains pricing, accounting, and final approval authority.

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Maintain Recurring Business Obligations

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·       Track rent, mail, registrations, licenses, and insurance/compliance renewal dates.

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·       Maintain a master task system with early reminders and responsible parties.

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·       Organize files and route incoming administrative information appropriately.

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Support Client Maintenance Records

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·       Enter and organize field service, inspection, and work-order data in the client maintenance-management system.

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·       Check submissions for completeness and maintain organized records.

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·       Help build repeatable processes for collecting and reporting field information.

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Provide Payroll and Reporting Backup

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·       Cross-train on payroll and union-reporting support. 

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·       Collect and prepare information per established procedures; protect confidential data.

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·       Route work for designated review—this role supports, but doesn't finalize, payroll decisions.

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Improve Systems as You Learn

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·       Turn on-the-job instruction into checklists, templates, and recurring Planner tasks.

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·       Work within Microsoft 365 (Planner, Outlook, Teams, Excel, shared files).

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·       Recommend practical ways to standardize or automate repetitive administrative work.

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WHAT MAKES YOU A GOOD FIT

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·       A track record of reliability and completing important work without repeated reminders.

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·       Comfort personally preparing documents, entering data, and following up until work is complete.

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·       Ability to manage work spanning days, weeks, and months without losing the next step.

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·       Clear writing and professional follow-up by email, phone, Teams, or in person.

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·       Sound judgment on what to handle independently versus escalate to leadership.

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·       Accuracy with documents, numbers, and confidential information.

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·       Comfort learning software and building reliable digital workflows.

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·       Motivation from direct ownership access and visible impact in a growing company.

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QUALIFICATIONS

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Required

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·       7+ years in executive support, business operations, office/project/contract administration, bookkeeping support, or a comparable role.

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·       3+ years directly supporting an owner, executive, or small-business leadership team.

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·       Demonstrated ability to work independently, prioritize, and drive follow-up to completion.

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·       Strong proficiency with Microsoft 365 (Outlook, Teams, Word, Excel, OneDrive/SharePoint, task tools).

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·       Experience building trackers, recurring workflows, checklists, or document-control processes.

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·       Strong written communication and professional follow-up skills.

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·       High discretion handling confidential business, payroll, and vendor information.

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·       Ability to work productively in an in-person, small-team environment.

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Preferred, But Not Required

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·       QuickBooks Online experience (estimates, purchase orders, invoices, transactions).

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·       Experience with contracts, subcontracts, insurance certificates, or compliance documentation.

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·       Purchasing, vendor coordination, and purchase-order tracking experience.

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·       Payroll, union reporting, certified payroll, or prevailing-wage documentation experience.

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·       Experience with a CMMS, work-order system, or field-service platform.

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·       Background in facilities management, construction, fire protection, government contracting, or healthcare facilities.

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You don't need experience in every function listed. We value transferable experience, sound judgment, initiative, and the ability to build dependable systems. We welcome candidates from organizations of any size who want a hands-on, small-team environment.

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HOW WE WORK

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This full-time, salaried position is based in our Westchester, Illinois office. Regular in-person collaboration matters, especially during onboarding while you learn our systems, priorities, and clients.

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Our workday typically starts earlier than 9:00 a.m. and wraps up around 4:00 p.m. We expect dependable availability and consistent follow-through during operating hours. We measure success by whether important work is organized, visible, and completed correctly—not by rigid desk time.

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Schedule flexibility may become available over time based on demonstrated proficiency and business needs. This is not a remote position, and flexibility is never guaranteed.

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COMPENSATION AND BENEFITS

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·       Budgeted annual base salary: $80,000–$95,000, based on experience, capabilities, and fit.

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·       Eligibility for discretionary company bonuses based on performance and contribution.

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·       Generous paid time off, managed responsibly around company needs and coverage.

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·       Practical flexibility and increasing autonomy as trust is established.

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·       Health insurance arrangements discussed in the final offer.

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·       Azimuth intends to expand benefits over time, including future retirement-plan options.

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HOW TO APPLY

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Please submit your resume and a brief response to this question: Tell us about a time you owned an important task that depended on other people. How did you keep it moving and ensure it was completed correctly without your manager having to chase it?

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Azimuth Contracting, LLC is an equal opportunity employer.