Executive Assistant

Why This Role Matters
As an Executive Assistant, you'll provide dedicated, high-trust support to Patriot's Chief Operating Officer and Chief Information Officer. By managing executive priorities, evaluating competing requests, and exercising independent judgment within delegated authority, you'll help both leaders focus their time and attention on critical business needs.

Your responsibilities will include complex calendars, travel, communications, and selected operational and technology assignments. You'll assess information, recommend solutions, and resolve matters within your authority while recognizing when executive decisions are needed. The role includes limited travel for occasional offsite meetings, conferences, or board sessions, along with occasional availability outside standard business hours.

How You'll Make an Impact
Own and manage the COO's and CIO's calendars, evaluating competing requests against business priorities, operational impact, risk, and decision deadlines.
Determine which requests require executive attention and which can be resolved, redirected, delegated, deferred, or declined within established decision rights.
Resolve competing demands within delegated authority, recommending tradeoffs and escalating conflicts that require executive alignment.
Prepare both executives for daily and weekly commitments with clear priorities, relevant background, and required materials.
Coordinate internal and external meetings, including agendas, participants, materials, logistics, and follow-up actions.
Arrange flights, hotels, ground transportation, and itineraries, responding promptly to last-minute travel and schedule changes.
Support leadership meetings, technology reviews, vendor discussions, operational planning sessions, and board-related engagements.
Draft and manage correspondence that accurately reflects each executive's voice, priorities, and direction.
Serve as an authorized contact for internal and external stakeholders, resolving inquiries and communicating executive direction within explicitly delegated authority.
Assess incoming issues for urgency and business impact, determine the appropriate response or escalation path, and prepare recommendations when executive decisions are required.
Handle confidential business, personnel, financial, operational, and technology information with discretion.
Evaluate sensitive matters and available response options, taking appropriate action within delegated authority and involving executives or functional specialists when needed.
Manage selected executive-sponsored operational and technology assignments from problem definition through completion, determining the approach, coordinating contributors, and evaluating alternatives.
Research and synthesize information into briefings, presentations, and reports that clearly identify issues, alternatives, risks, business implications, and recommended actions.
Track executive commitments and deadlines, assess delivery barriers, and recommend changes to sequencing, responsibilities, or approach when needed.
Coordinate activities related to technology implementations, IT governance, operational improvements, and cross-functional projects.
Partner with other executive assistants and teams across IT, Operations, Finance, HR, and other functions to maintain communication and follow-through.
Recommend improvements to executive-office workflows and implement approved changes that strengthen prioritization and decision readiness.

Who You Are
A polished, trustworthy professional who handles sensitive information with sound judgment and discretion.
Proactive and organized, anticipating needs and bringing structure to changing priorities.
Comfortable making independent decisions within clear boundaries and recognizing when to escalate.
Calm and resourceful under pressure, including last-minute changes and competing executive demands.
A clear communicator who represents senior leaders accurately and professionally.
Technologically comfortable and able to navigate IT leadership conversations and priorities.
Adaptable to two executives with different working styles, preferences, and business needs.
Accountable for follow-through, with the ability to turn ambiguous requests into clear actions and recommendations.

What You Bring
Day One:
7+ years of experience supporting senior executives at the VP level or above, including complex calendar and travel management.
Prior experience providing direct administrative support to a senior technology leader, such as a CIO, CTO, SVP of IT, or comparable executive.
Familiarity with corporate IT operations and priorities, including technology initiatives, vendor relationships, systems implementations, and cross-functional coordination.
Demonstrated experience supporting multiple senior leaders or managing competing executive priorities.
Experience exercising delegated authority on substantive executive-office or business matters, evaluating alternatives, resolving issues without detailed instructions, and recognizing when executive approval is required.
Ability to assess business implications, synthesize information from multiple stakeholders, and prepare clear, actionable recommendations.
Demonstrated ability to protect highly confidential information.
Excellent written and verbal communication skills.
Strong proficiency with Microsoft 365, including Outlook, Teams, PowerPoint, and Excel, along with standard travel and expense platforms.
Ability to anticipate needs, manage up, and adjust quickly to shifting priorities.
Availability for limited travel and occasional support outside standard business hours.

Valuable Additions:
Experience supporting a CIO or CTO within a complex organization with multiple locations.
Experience in insurance, brokerage, financial services, or another professional services industry.
Experience supporting executives in an acquisition-driven or multi-entity organization.
Familiarity with enterprise technology initiatives, IT leadership meetings, vendor management, cybersecurity discussions, or systems transformation projects.
Experience preparing and coordinating materials for executive leadership or board meetings.
Experience supporting both operational and technology leadership functions.
Certified Administrative Professional (CAP), Project Management Professional (PMP), or equivalent experience.