Executive Assistant

Role Summary

Milele is scaling from a fast-growing trading business to a disciplined systems-led organization with Fortune-500 ambition. The Executive Assistant (EA) to the CEO is the force-multiplier for the chief executive owning the CEOs time priorities and information flow; creating visibility and cadence; and ensuring follow-through on critical decisions.

Key Responsibilities

• Time & Prioritization: Own the CEO's calendar, travel and daily agenda; protect focus time. Apply time ROI triage anti-meeting rules and escalation protocols. Ensure pre-reads/decision memos and options are ready for each meeting. Prepare meeting briefs with objectives, context, risks and talking points. Capture decisions/actions in real time; ensure follow-up completion.
• Operating Cadence & Program Management: Run WBR/MBR/QBR with agendas, scorecards and concise narratives highlighting deltas, risks and asks. Track company-wide strategic initiatives (owners, dates, risks); escalate blockers early.
• Communications & Stakeholder Management: Draft internal/external communications on behalf of the CEO (emails, memos, speeches, LinkedIn). Prepare board and investor materials; manage logistics and minutes with discretion. Represent CEO with investors, suppliers and public officials. Synthesize ambiguity into 1-page briefs using Pyramid Principle / MECE. Maintain live Decisions & Actions Log; ensure downstream alignment. Apply professional gatekeeping with judgment and tact.
• Information Documents & Knowledge Management: Maintain a single source of truth for CEO files, briefs and templates (Teams/SharePoint). Standardize and enforce document templates and hygiene. Manage access control, auditability and confidentiality.
• Travel, Events & Logistics: Plan complex international travel with cost/risk controls. Organize leadership offsites, VIP visits and high-stakes meetings end-to-end. Provide limited personal support to ensure seamless execution.
• Automation & Tools (AI First): Use Microsoft 365 Teams Power Automate for workflow orchestration. Leverage generative AI (ChatGPT, Claude, Gemini) for summarization, drafting and research. Build basic dashboards in Excel/Power BI.

Professional Standards

• Availability: On-call across time zones; quick response (15 min within working hours, 60 min after hours).
• Quality: Zero-defect mindset; double-check all names/numbers; cite sources.
• Writing: Concise, decision-oriented executive summaries first; bullet points preferred.
• Professional Presence: Calm under pressure; respectful challenge when needed.
• Client Service: Anticipatory, discreet, proactive.
• Work Ethic: Comfortable with extended hours as in elite consulting/IB environments.
• Compliance: DA signed background checks cleared; anti-bribery and data privacy adherence.

Qualifications & What Were Looking For

Education:

• Bachelors degree required (Business, Communications, Operations or related).
• Masters/MBA preferred.

Experience:

• 6 years supporting C-suite/founders in high-growth or multi-country organizations.
• Demonstrated success implementing executive cadences (OKRs, WBR/MBR, board packs).
• Proven experience working directly with a UHNWI CEO/Chairman/Founder in a fast-paced high-stakes environment.

Technical Skills:

• Advanced Microsoft 365: Outlook, Teams, SharePoint, Excel (pivots/lookups), PowerPoint.
• Comfortable with workflow tools and dashboards.
• Strong document control and knowledge management habits.

Communication & Leadership:

• Exceptional writing and synthesis skills.
• High EQ, mature judgment, impeccable discretion.
• Systems thinker focused on leverage and time savings.

Languages:

• Excellent spoken/written English required.

Nice to Have (Differentiators)

• Certifications: CAP (IAAP), PMP (PMI) or equivalent.
• Experience in fundraising, investor relations or board governance.

Cultural Fit & Mindset

This role is not for everyone. You will be working directly with a UHNWI CEO/Founder in a high-stakes, high-velocity environment where expectations are on par with elite consulting, investment banking and global leadership offices.

The right candidate will:

• Thrive under pressure and maintain composure even when timelines are tight and stakes are high.
• Be solution-oriented, anticipating problems before they arise and proposing clear options with pros/cons.
• Operate with total discretion; confidentiality is non-negotiable.
• Embrace direct, concise communication and welcome respectful challenge to achieve the best outcome.
• Show extreme ownership — if it\'s yours, it\'s done without handholding.
• Adapt quickly to changing priorities, time zones and last-minute shifts in the CEO\'s schedule.
• Possess a service mindset without being subservient; proactively supporting while protecting priorities.
• Maintain high personal standards in appearance, professionalism and ethics at all times.

If you\'re looking for a comfortable predictable 9-to-5 job this is not the role for you. If you want to operate at the highest level, create massive leverage for a top CEO and be trusted with sensitive business-critical matters we want to hear from you.

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