Executive Personal Assistant

Your Other Half; United States; Remote; USD 30,000 - 73,000; Full time

Job summary

Join a dynamic team as an Executive & Personal Assistant to the CEO at a leading remote organization. This role requires exceptional skills in digital organization, communication, and proactive support to streamline operations and prioritize effectively. You'll help manage the CEO's schedule and communications while driving organizational efficiency. We value teamwork, creativity, and a commitment to delivering quality results in a fast-paced environment.

Benefits

Paid holidays

Paid sick time

Weekly exercise class

Unlimited PTO if converted

Medical, dental, and vision insurance

401(k) with 3% match

$50/month wellness benefit

Annual professional development stipend

Qualifications

• 5+ years of Executive Assistant experience.
• 2+ years of remote work experience.
• Experience managing a founder or CEO's workflow.

Responsibilities

• Manage the CEO’s calendar, inbox, and travel.
• Draft and edit internal and external content.
• Organize and maintain documents according to SOPs.

Skills

Time-blocking

Digital organization

Project flow

Communication

Attention to detail

Proactive organization

AI tools usage

Tools

Asana

Google Suite

Slack

Zoom

Dex

Harvest

Job description

3 days ago Be among the first 25 applicants

Your Other Half - 100% Remote - Location = EST

Do you thrive on turning chaos into clarity, creating order, and building efficient systems? Do you stay grounded in fast-paced environments and love turning big ideas into real progress? Do you naturally bring calm focus and enthusiastic momentum to the leaders you support?

If so, you might be the Executive & Personal Assistant we’re looking for.

What You’ll Own

As our Executive & Personal Assistant, you’ll be the right-hand to our CEO—protecting her time, managing communications, streamlining workflows, and building systems to keep Your Other Half (and her life) running smoothly. This is a high-trust, high-autonomy, high-impact role where you’ll drive priorities forward and anticipate what’s next.

What You’ll Do

• Manage the CEO’s calendar, inbox, meetings, and travel—from daily logistics to long-term planning.
• Triage and respond to all communication across platforms (email, phone, Slack, social inboxes) quickly and clearly.
• Maintain relationships on the CEO’s behalf with professionalism, clarity and good judgement, including clients, prospects, vendors, and personal contacts.
• Track and update notes, documents, and workflows in Asana, Harvest, Google Drive, Dex, and shared calendars.
• Organize and file documents and information following SOPs, especially in the CEO’s workspace.
• Draft and edit internal and external content: emails, proposals, SOPs, and marketing copy.
• Design and refine workflows using AI tools for efficiency and clarity.
• Support personal logistics like appointments, errands, and travel.
• Proactively spot issues, anticipate needs, and solve problems before they arise.

What Success Looks Like

• The CEO’s schedule is aligned with business and personal priorities.
• Communication is streamlined, timely and brand-aligned.
• Key relationships are maintained professionally, even when the CEO is unavailable.
• Systems are smart, streamlined, and easy to use.
• Personal tasks are handled timely and discreetly, enabling deep work.
• Deadlines are met, projects stay on track, and the CEO feels supported.

Schedule: 8:00 AM-6:00 PM ET weekdays with a daily 1-hour lunch break

Location: Remote

Compensation: $30.00 per hour with overtime (with a pay increase post-contingency period)

Travel: Up to 8 weeks/year (currently 2-4 weeks/year)

Reports to: CEO

Start Date: June 2, 2025, or any Monday thereafter

About You

You’re a builder, fixer, and systems thinker. You take ownership, communicate clearly, and thrive in fast-paced environments. You find deep satisfaction in helping high-performing leaders stay in flow.

Must-Haves

• 5+ years of Executive Assistant experience, including 2+ years remote work experience.
• Experience managing the life and workflow of a founder or CEO.
• Skilled in time-blocking, digital organization, and project flow.
• Clear, warm communication and strong follow-through.
• Strong attention to detail and proactive organization.
• Proficient in Asana, Google Suite, Slack, Zoom, Dex, and Harvest (at least 4).
• Experience using AI tools to increase efficiency.
• Based in the continental U.S. with full work authorization.

Bonus Points

• Have built strong, long-term executive support relationships.
• Follow thinkers like Dan Martell, Brooke Castillo, Kim Scott, or Gino Wickman.

Why Join Us?

At Your Other Half, we’re building a culture where you’re set up to do your best work. We lead with curiosity, care deeply, take ownership, move through challenges as a team, and always make space for fun.

Our Hiring Process

• Why are you interested in this position?
• What do you know about our company?
• What is your ideal work environment?
• What are your strengths?
• Initial phone chat (30 min): Quick background conversation.
• CliftonStrengths 34: We’ll cover the cost to understand your work style.
• CEO Interview (1 hour): Get to know each other and explore alignment.
• Paid Test Project (2 hours): Work with us on a real task.
• Team Interview (1 hour): Confirm fit with our leadership team.
• Offer: If we’ve enjoyed working together, we’ll invite you to join the team.

We appreciate your time and effort. Every application is reviewed, and we aim to respond within

30 days. Your Other Half is an equal opportunity employer. We believe diverse teams create better business results, and we’re committed to building a company that reflects the people and businesses we serve.

Immediately upon hire: Paid holidays | Paid sick time | Weekly exercise class | Remote work

If converted to a regular position after 90 days: Unlimited PTO | Medical, dental, and vision insurance (50% employee-only premium paid) | Short-term disability, long-term disability, and life insurance (100% paid) | Retirement plan with 3% match | $50/month wellness benefit | Annual professional development stipend

About Your Other Half

At Your Other Half, we help small business leaders build, manage, and strengthen their teams. Our team of small business people experts brings over 122 years of combined experience in HR, recruiting, and leadership development. We work hands-on with impact-driven leaders to build people systems that drive confident leadership, sustainable growth, and strong, healthy teams.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Administrative, General Business, and Human Resources

• Industries

  Human Resources Services

Referrals increase your chances of interviewing at Your Other Half by 2x

Inferred from the description for this job

Medical insurance

401(k)

Vision insurance

Paid maternity leave

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