Executive Assistant at WinChoice – Mountain Pine, Arkansas

Executive Assistant to the CEO

High-Trust | High-Impact | High-Growth Role

This is not a traditional Executive Assistant role.

Our CEO is a visionary, fast-moving, big-picture thinker who operates at the speed of growth. Ideas move quickly. Priorities evolve. The right person in this role won’t just keep up—they’ll help create order, momentum, and clarity in the middle of it all.

We’re looking for someone who sees this position as a career accelerator: high responsibility, high exposure, and high expectations.

The Role

You’ll serve as the CEO’s primary support partner, helping protect their time, sharpen their focus, and drive execution across the organization. Your job is to anticipate, organize, follow through, and keep things moving forward—even when things are moving fast.

You’ll be trusted with sensitive information, big decisions, and direct access to leadership. This role requires judgment, confidence, adaptability, and a strong bias toward action.

What You’ll Do

• Manage and protect the CEO’s calendar, priorities, and time—ensuring focus on the highest-impact work
• Anticipate needs by preparing materials, context, and follow-ups ahead of meetings and decisions
• Keep the CEO organized and grounded as priorities shift and new ideas emerge
• Track and follow up on action items, commitments, and deadlines across departments
• Help drive execution on key initiatives, projects, and communications
• Act as a gatekeeper and filter, saying “no” when needed and creating space for what matters most
• Serve as a thought partner, someone the CEO invests in professionally while you help them grow as a leader
• Move fast without complaining—this is a growth environment, and speed is part of the job

Who You Are

• Exceptionally organized, proactive, and calm under pressure
• Comfortable working with a leader who moves fast, thinks big, and doesn’t always slow down to explain every step
• Able to create structure without stifling creativity
• Direct, grounded, and confident enough to push back respectfully when needed
• High emotional intelligence—you read the room, anticipate tension, and keep things respectful and productive
• Thick-skinned, adaptable, and not easily rattled
• Discretion and trust are non-negotiable
• Technically adept: MS Office skills are essential and the ability to embrace new tech as needed

Culture & Fit

Our CEO is direct, passionate, and human. He cusses—but never at people. He’s always respectful, values honesty, and expects the same in return. This role requires someone who can operate comfortably in that environment and doesn’t need hand-holding or constant reassurance.

Why This Role Is Different

• You’ll have direct exposure to leadership, strategy, and decision-making
• You’ll be trusted early and often
• You’ll grow fast—professionally and personally
• This role is what you make of it; the ceiling is high

If you’re looking for a comfortable assistant role, this isn’t it.
If you’re looking to accelerate your career alongside a CEO building something meaningful—this might be exactly what you’re looking for.