Job Description
We’re partnering with a founder/CEO of a boutique coaching and advisory practice that supports senior executives and private equity-backed leadership teams at critical inflection points. We're looking for a high-trust, long-term Executive Assistant who can operate as a true right hand - someone proactive, detail-oriented, and strong in communication. This is a fully remote role in Costa Rica or Colombia working 9:30am – 5:30pm EST.
This isn’t just a task-based EA role - you’re stepping in as a true partner to the executive. You’ll be deeply involved in keeping both the professional and personal side of the business running smoothly, with a high level of trust and autonomy. If you’re someone who enjoys making everything run seamlessly and you take pride in being proactive, organized, and reliable - this could be a great fit.
What You’ll Do
• Own and manage an extremely high-touch calendar - protecting time, planning ahead, and resolving conflicts before they happen
• Act as “traffic control” for a fast-moving schedule with senior executives and CEOs
• Help prepare for clients and meetings – pull together bios, background briefs, and pre-read summaries
• Manage inbox and draft clear, polished communication on behalf of the executive
• Coordinate travel (flights, hotels, itineraries) and logistics
• Support offsite preparation: agendas, slides, surveys, participant materials
• Stay on top of follow-ups, trackers, and workflows so nothing slips
• Handle some personal logistics (appointments, household, healthcare reimbursements, pet insurance, light bill pay, reservations)
• Support light business admin tasks (prepare proposals, contracts, monthly invoicing inputs, and expense reports)
We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.
Required Skills & Experience
What We’re looking For
• Strong English proficiency - both written and verbal
• Strong calendar management skills (this is a must-have)
• Highly organized with exceptional attention to detail (time zones, links, invites, etc.)
• Proactive - you’re always thinking a few steps ahead
• You’ve supported a founder, executive or other senior professional
• Comfortable operating in a high-trust, fully remote environment
• You'd rather be the calm, capable center of a small practice than one of many in a large corporate environment
Tools
• Comfort with Google Workspace. Gmail, Calendar, Drive, Docs, Sheets.
• Strong with spreadsheets. The practice runs on a tracker with formulas, structured tabs, and data.
• Experience with Outlook.
• Comfort using Claude or other AI tools, and willingness to learn new tools as needed.
• Canva and/or Google Slides experience for offsite and presentation materials is a plus.
• Experience preparing bios, briefs, and pre-meeting materials.
• Comfort coordinating with other senior EAs as a peer.
Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.