Executive Assistant To Ceo – Real Estate Investment Firm

Remote | Full-Time | U.S. Applicants Only

How to Apply
To apply, send both a resume and a short cover letter to team@winnco.net
Subject line: Executive Assistant Application

About Us:

We’re a fast-moving, family-owned real estate investment and development firm with a big vision: to create long-term value through land development, strategic acquisitions, and high-impact projects. We’re lean, entrepreneurial, and hands-on — operating at the intersection of hustle and heart.

We’re building something lasting, and we need the right people to help shape it!

Why This Role Matters:

This isn’t a traditional EA job focused on inboxes and calendars. This is a high-trust partnership with the CEO — designed for someone who’s ready to learn the business inside and out, wear multiple hats, and become a critical operations partner as we scale.

We’re looking for someone who’s hungry to grow, obsessed with execution, and ready to help bring big vision to life — one strategic step at a time.

You won’t just support — you’ll lead, organize, implement, and streamline. You’ll help drive our business forward by taking real ownership of marketing, systems, and daily execution — while keeping the CEO laser-focused on what matters most.

Who We’re Looking For:

✅ A self-starter who thrives in entrepreneurial environments and is energized by growth

✅ Excited to work side-by-side with a founder to scale operations and build something meaningful

✅ Experienced in real estate — you've spent 2+ years in investing, development, brokerage, or a related field

✅ Passionate about marketing — you understand funnels, KPIs, and what makes campaigns perform

✅ Organized and systems-minded — you think in workflows, automations, and SOPs

✅ Tech-forward — you love testing new tools, working with CRMs, and exploring AI

✅ A proactive doer — you solve problems before they’re voiced, and you get stuff done

✅ Looking to get out of the corporate grind and into a tight-knit, mission-driven team

What You’ll Do:

⚙ Own Daily Execution

• Help the CEO stay focused by taking lead on daily priorities, tasks, and project management
• Keep operations and marketing initiatives on track and moving

⚙ Support Marketing & Metrics

• Coordinate and support marketing campaigns
• Track performance, manage content calendars, and support data-driven decision-making
• Help develop and refine a company-wide KPI dashboard

⚙ Build & Optimize Systems

• Identify inefficiencies, build out SOPs, and help streamline core business workflows
• Implement tools, automations, and AI to create leverage

⚙ Wear Multiple Hats

• Jump in on projects across title coordination, dispositions, and land development
• Step into key roles temporarily to evaluate systems and scale effectively
• Work directly with the CEO to build new entities, processes, and teams as we grow

Why Join Us

✨ You’ll be part of a family-run business

✨ You’ll work directly with the founder and have a true seat at the table

✨ You’ll wear many hats, grow fast, and make a real impact

✨ You’ll have ownership, flexibility, and room to grow into a key leadership role

✨ You’ll be part of a values-driven, high-trust, and mission-focused team

This is a launchpad — not a landing spot. If you’re ready to grow into an operator, help build something meaningful, and be part of a business that values people just as much as performance, we want to hear from you.

How to Apply
To apply, send both a resume and a short cover letter to team@winnco.net
Subject line: Executive Assistant Application

Applications that don’t follow these instructions will not be reviewed

U.S. applicants only — this is a remote role, but we require U.S. residency

Job Types: Full-time, Part-time

Pay: $40,000.00 - $50,000.00 per year

Expected hours: 30 – 40 per week

Benefits:

• Paid time off

Work Location: Remote