Executive Assistant
Headstart Warranty Group
Salary: $70,000–$80,000 annually, depending on experience
Bonus: Bonus structure to be determined at the time of hire
Experience: 10+ years of relevant Executive Assistant experience preferred
Headstart Warranty Group is seeking a highly experienced, confident, and exceptionally dependable Executive Assistant.
This is not a passive administrative role. We are looking for someone with strong character, excellent judgment, a strong work ethic, and the confidence to take ownership of schedules, priorities, meetings, and day-to-day demands.
The right person must learn quickly, listen carefully, retain information, and develop a strong understanding of how leadership thinks, works, communicates, and prioritizes. This person should anticipate needs and minimize the amount of time leadership spends repeating instructions, tracking down information, or dealing with matters that can be handled or resolved independently.
What You'll Do
- Manage and protect executive schedules, time, and priorities
- Serve as a gatekeeper for requests, meetings, and interruptions
- Find out what someone needs before escalating a matter to leadership
- Gather the necessary information and context before involving leadership
- Determine what can be handled, delegated, redirected, or resolved independently
- Be confident saying no, pushing back, or redirecting people when necessary
- Ask the right questions and quickly understand what needs to be accomplished
- Listen carefully and retain important information from conversations
- Take accurate notes and keep track of verbal instructions, commitments, and follow-up items
- Learn leadership preferences, priorities, communication styles, and decision-making processes
- Remember previous conversations, instructions, names, details, and decisions
- Connect information from different conversations and recognize when something needs attention
- Anticipate needs before being asked
- Manage complex calendars and proactively resolve scheduling conflicts
- Prioritize meetings and requests based on importance and business needs
- Plan and coordinate internal and external meetings
- Prepare agendas, documents, reports, presentations, and other meeting materials
- Coordinate conferences, executive events, and business engagements
- Arrange travel, accommodations, itineraries, transportation, and related logistics
- Occasionally travel when business needs require it
- Track deadlines, decisions, commitments, and outstanding items
- Follow up with employees, leaders, vendors, and outside contacts when information or action is needed
- Handle confidential and sensitive information with discretion
- Keep priorities moving without requiring constant direction or reminders
Qualifications
- 10+ years of Executive Assistant or senior-level administrative experience preferred
- Must be highly proficient in Microsoft Word, Excel, PowerPoint, etc..
- Strong overall computer and technology skills
- Must be comfortable learning new systems, software, and technology
- Ability to learn unfamiliar software and systems quickly with minimal instruction
- Comfortable adapting when the company implements new technology, processes, or tools
- Resourceful enough to troubleshoot, research, and figure out new systems independently
- Ability to create, edit, organize, and format professional documents and spreadsheets
- Strong character and confidence
- Extremely dependable and trustworthy
- Fast learner who can absorb and retain information quickly
- Exceptional listener with strong retention and memory
- Able to ask thoughtful and relevant questions to quickly understand what leadership needs
- Remembers conversations and does not need the same information repeatedly explained
- Highly observant and able to recognize patterns, preferences, and priorities
- Confident enough to say no when necessary
- Comfortable pushing back and establishing boundaries
- Protective of leadership’s time and priorities
- Not easily intimidated by titles, personalities, or pressure
- Professional, direct, assertive, and respectful
- Excellent judgment and discretion
- Highly organized with exceptional attention to detail
- Proactive rather than reactive
- Resourceful and able to solve problems independently
- Comfortable making appropriate decisions without waiting for constant direction
- Able to adjust quickly when priorities change
- Strong written and verbal communication skills
- Takes ownership and follows responsibilities through to completion
- Willing to learn and receptive to feedback
Compensation
The anticipated salary range is $70,000–$80,000 annually, depending on experience and qualifications.
A bonus structure will be discussed and determined at the time of hire.
The Person Who Will Succeed Here
We are looking for someone who understands that being an Executive Assistant means much more than managing a calendar.
You need to be a strong gatekeeper who understands the value of executive time. When someone needs access to leadership, your first responsibility is to understand what they need, gather the information, determine whether you can resolve or redirect it, and decide whether leadership actually needs to be involved.
You must be comfortable protecting executive time, even when that means saying no, redirecting someone, pushing back, or requiring additional information before scheduling a meeting.
Just as importantly, you need to learn quickly. Listen when people speak. Ask good questions. Remember the answers. Learn preferences and priorities. Pay attention to how decisions are made and what information is important.
You also need to be comfortable with technology. We need someone who can be introduced to a new system or software and learn it quickly. You should be willing to explore, troubleshoot, research, and figure things out rather than immediately depending on someone else to walk you through every step.
As you learn the role, you should become increasingly capable of anticipating needs, recognizing what is important, and knowing what requires attention without needing constant instruction.
If you need every step explained, frequently need instructions repeated, have difficulty learning new technology, have difficulty setting boundaries, or are uncomfortable dealing with strong personalities, this will not be the right role.
If you listen closely, learn quickly, remember details, take ownership, protect priorities, adapt to new technology, and naturally stay several steps ahead, we want to meet you.