Executive Assistant

Patriot Growth Insurance Services | United States | Remote | Full-Time

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.

Real Benefits for Real Life

At Patriot, great benefits mean more than coverage; they mean being there through every stage of life: your health, your family, your financial future, or simply time to recharge. Whether you're working or not, life doesn't stop. Neither should your benefits.

Highlights Include:

• Multiple medical plan options, with preventive care covered at 100%
• Free virtual medical and mental healthcare for employees and their families, plus a dedicated healthcare concierge to help you navigate benefits, compare prescription costs, and make more confident, personalized care decisions
• Employer-paid short-term and long-term disability coverage
• Paid parental leave
• Personalized PTO that lets you take time away when you need it, without traditional accruals, plus separate sick leave
• Competitive 401(k) company match to help you build your financial future
• Comprehensive dental and vision coverage
• Employee Assistance Program with confidential mental health, legal, financial, and work-life support

About Patriot Growth Insurance Services

At Patriot, we build our teams around a simple idea: people do their best work when they feel supported as whole people, not just managed as employees. We're invested in your growth, not just your output, and we back that up with a competitive salary and a comprehensive health and welfare program that extends to your family and domestic partners too, because who you're building a life with matters to us as much as the work you do.

Founded in 2019, Patriot is a growth-focused national insurance services firm that partners with employee benefits and property and casualty agencies across the United States. We're currently ranked the 25th-largest broker in the U.S. by Business Insurance and were named to the 2025 Inc. 5000 list of fastest-growing companies. With over 2,100 employees operating in 150+ locations across more than 45 states, our collaborative model gives every person and every agency the resources and support they need to grow, while each agency keeps its own identity, culture, and way of doing business. That growth has never been about numbers alone; it's about the people behind them.

Patriot Growth Insurance Services is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, citizenship or immigration status, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, leave of absence, compensation, benefits, and training. Patriot makes hiring decisions based solely on qualifications, merit, and business needs at the time. For more information, read through our EEO and DE&I Policy located on our website at www.patriotgis.com.