Executive Personal Assistant to Entrepreneur Job at Pocketbook Agency, Manhattan, IL

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  • Pocketbook Agency
  • Manhattan, IL

Job Description

JRN: 2124

We’re seeking a sharp, resourceful Executive Personal Assistant with a strong background in marketing and public relations to support a high-level executive across professional ventures, creative projects, and personal tasks. This unique role is ideal for someone who thrives in a fast-paced, entrepreneurial environment and loves wearing multiple hats from running high-level marketing initiatives to managing daily logistics. The breakdown of responsibilities is split between marketing/PR, executive assistance, and personal assistance.

Requirements:

  • 5–10 years of experience in marketing, public relations, and/or high-level entrepreneurial support is highly preferred
  • Proven ability to ideate, implement, and evaluate marketing campaigns (digital + experiential)
  • Comfortable doing deep-dive research on niche topics (ex: AI-generated campaigns, obscure creative tech, nonprofit integration strategies)
  • Strong communication and vendor management skills
  • Experience coordinating influencer partnerships and securing media exposure (podcasts, press, social campaigns)
  • Exceptionally organized and self-directed with the ability to manage multiple concurrent projects
  • Comfort around animals/pet friendly and ability to coordinate vet visits or care when needed
  • Technologically fluent, especially in AI tools, marketing platforms, and digital research
  • Must be based near or able to commute regularly to the south Chicago area

Responsibilities:

Marketing & PR

  • Plan and run social media campaigns, email newsletters, and broader PR efforts across various ventures
  • Research and implement innovative marketing tools including AI-powered content and campaign automation
  • Coordinate influencer campaigns, securing talent and overseeing deliverables
  • Build, test, and optimize marketing funnels and donation initiatives for charitable ventures including handoff and documentation
  • Hire and manage creatives (graphic designers, illustrators, artists) to produce assets for various projects
  • Develop timelines, briefs, and performance recaps for each campaign
  • Secure and coordinate podcast interviews and media opportunities

Executive Assistant

  • Manage calendar scheduling across business, creative, and philanthropic obligations
  • Book complex domestic and international travel itineraries
  • Oversee inbox management, draft professional correspondence, and coordinate with internal and external stakeholders
  • Implement systems for communication, project tracking, and relationship management
  • Manage logistics and execution for various business concepts including new launches, charitable initiatives, and partnership implementations
  • Help with the hiring and onboarding of creative contractors and freelancers
  • Support remote ranch management in Texas by coordinating vendors and ensuring project updates

Personal Assistant

  • Run location-appropriate errands (stacking when possible) including but not limited to:
  • Dry cleaning drop-off and pick-up
  • Prescription pickup
  • Mail and package management
  • Occasional grocery runs or gift sourcing
  • Coordinate vet appointments and household needs
  • Maintain a basic rhythm of personal task support that respects time, geography, and efficiency

Schedule:

Monday to Friday, 9 AM to 5 PM

Compensation:

$80-120K, depending on experience, 80% employer-paid healthcare (PPO plan), unlimited PTO, and additional perks

Location:

Chicago, IL (South Chicago/Manhattan region)

Job Tags

For contractors, Freelance, Remote work, Monday to Friday,

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