Job Description

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
1) Time & Prioritization

• Own the CEOs 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.

2) 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.

3) 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.

4) 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.

5) 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.

6) 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 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/Founderin ahigh-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 its yours, its done to the highest standard without handholding.

• Adapt quickly to changing priorities, time zones, and last-minute shifts in the CEOs 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.