Pocketbook Agency

Compensation

Full Description

A private tech entrepreneur is seeking a highly organized, intuitive, and tech-savvy Remote Executive/Personal Assistant/Lifestyle Manager to provide comprehensive support across business, lifestyle, wellness, and social domains. This is a unique role for someone who thrives in a fast-moving environment, loves problem-solving, and can anticipate needs before they're mentioned. The ideal candidate is proactive, discreet, thick-skinned, and comfortable supporting a high-achieving principal with diverse personal and professional priorities, ranging from operations and scheduling to wellness, gifting, social planning, and travel coordination. Responsibilities: • Monitor inboxes, flag priority messages, and respond or draft replies as needed • Proactively manage calendar and schedule meetings in 15/30/45/60-minute blocks • Add travel buffers, manage time zones, and ensure seamless coordination with internal and external teams • Book all travel, accommodations, reservations, and related logistics • Maintain a running list of pending responses and follow-ups • Support interview scheduling, travel for candidates, and onboarding workflows • Assist with end-of-year tax preparation (personal + company coordination) • Coordinate legal and administrative tasks (document signatures, filings, virtual mail, etc.) • Oversee mail handling, virtual mail services, and operational admin requirements • Schedule all recurring personal appointments (PT, yoga, haircut, doctor, massage, etc.) • Research, purchase, and manage personal items (electronics, wellness devices, household purchases) • Keep the principal updated on new tech releases (iPhone/MacBook refresh cycles, etc.) • Support nutrition, health, and wellness goals, including sourcing chefs, massage specialists, and wellness service providers • Coordinate family-related needs and birthday gifts • Help plan dinners, brunches, small events, and travel with friends • Coordinate guest lists, logistics, reservations, and experience flow • Maintain a gifting calendar and ensure timely, thoughtful gifts are sent for birthdays and key dates • Collaborate with friends’ assistants and team members for group coordination • Suggest events, trips, and experiences aligned with preferences • Re-share posts via company socials • Flag meaningful DMs across LinkedIn, Twitter, and email for follow-up • Monitor replies and sentiment • Monitor inbox for scheduling requests; cc yourself and archive when appropriate • Anticipate needs, propose improvements, and keep the principal organized • Work seamlessly with an on-site house/office manager to delegate physical tasks Requirements: • 5+ years supporting a founder, entrepreneur, investor, or UHNW individual • Experience working remotely in a fast-paced, high-volume environment • Exceptional written communication and rapid-response capability • Tech-savvy: proficient in Google Suite, Slack, automation tools, task platforms, and general digital literacy • Thick-skinned, assumes good intent, and comfortable with concise communication styles • Strong judgment, confidentiality, and emotional intelligence • Ability to handle both high-level strategic tasks and everyday personal errands • Comfort working around individuals with diverse viewpoints; not overly sensitive or politically rigid • Proactive, anticipatory mindset, able to stay several steps ahead • Responsive during EST weekday hours; weekend standby required Schedule: 24/7 mentality required Compensation: Up to $220K+ based on experience, healthcare coverage, PTO, bonus Location: Remote on EST