About the CEO

Yoshi Yokokawa is Co-Founder and CEO of Alpaca. With experience across investment banking and entrepreneurship, he leads Alpaca’s mission to democratize financial services through developer-centric platforms. He has been recognized internationally, including selection as an Endeavor Entrepreneur.

Role Summary

We are seeking a highly proactive Executive Assistant to serve as a strategic partner and force multiplier to the CEO. This role goes beyond administrative support — you will protect the CEO’s focus, manage complex global priorities, and drive cross-functional accountability in a fast-moving fintech environment.

You operate with sound judgment, high emotional intelligence, operational rigor, and discretion — anticipating needs, eliminating friction, and ensuring execution without bottlenecks.

Key Responsibilities

Strategic Calendar & Time Management

• Own and optimize the CEO’s calendar across global time zones, aligning time to highest business priorities.
  
  
• Protect deep-work blocks, investor meetings, regulatory discussions, off-sites, and strategic engagements.
  
  
• Prepare high-quality briefing materials and pre-reads.
  
  
• Anticipate conflicts and rapidly reprioritize based on urgency and impact.
  
  
• Act as a strategic gatekeeper — distinguishing urgency from noise and protecting executive leverage.

Executive Communication & Inbox Ownership

• Serve as primary point of contact for internal leaders and external stakeholders (investors, board members, regulators, partners, senior customers).
  
  
• Fully triage and manage a high-volume global inbox; draft, delegate, and maintain a zero-lag follow-through system.
  
  
• Draft and refine high-impact communications aligned with the CEO’s voice and Alpaca’s mission.
  
  
• Ensure timely escalation of critical decisions and commitments.

Board, Leadership & Stakeholder Coordination

• Coordinate board and leadership materials, including agendas, logistics, minutes, and action tracking.
  
  
• Support flow of sensitive information with strict confidentiality.
  
  
• Interact professionally with C-suite executives, investors, regulators, and enterprise stakeholders.

Project Coordination & Cross-Functional Execution

• Track CEO-level initiatives and action items; drive accountability across teams.
  
  
• Support strategic initiatives including investor relations, partnerships, global licensing, customer escalations, and executive planning.
  
  
• Maintain dashboards, documentation, timelines, and status updates to ensure execution without bottlenecks.
  
  
• Proactively identify risks, blind spots, and operational inefficiencies.

Operational Excellence & Systems Optimization

• Improve executive workflows, communication systems, and internal processes to increase scale and velocity.
  
  
• Coordinate NDAs, vendor onboarding, presentations, and operational infrastructure.
  
  
• Build reliable systems for meetings, decisions, and stakeholder management.
  
  
• Recommend process improvements that enhance executive productivity.

Global Travel & Event Management

• Plan and execute complex multi-country travel, including visas, budgets, contingency planning, and regulatory or board meetings.
  
  
• Support participation in high-profile industry events and external engagements.

What Success Looks Like

• The CEO’s time is focused on the highest-value activities.
  
  
• Communication across teams and stakeholders is timely, clear, and frictionless.
  
  
• Projects under the CEO’s remit remain on track and well-managed.
  
  
• External partners experience a responsive, professional executive office.
  
  
• The EA anticipates needs and executes independently with minimal direction.

Goals & Performance Indicators

• Executive Responsiveness: 95% of priority emails and stakeholder communications addressed within 1 business day.
  
  
• Calendar Precision: Maintain <5% scheduling conflicts or preventable reschedules per quarter.
  
  
• Execution Reliability: ≥98% of tracked action items and commitments delivered on time.
  
  
• Travel & Logistics Accuracy: 100% adherence to executive preferences, budgets, and timelines.
  
  
• Stakeholder Satisfaction: ≥85% executive and leadership satisfaction with support effectiveness.
  
  
• Presentation & Materials Quality: Consistently deliver high-quality executive materials on time, meeting clarity and professionalism standards.

Who You Are

Experience

• 5+ years supporting C-suite executives in technology, fintech, financial services, or high-growth startups.
  
  
• Experience operating in fast-paced, globally distributed environments.
  
  
• Experience working with senior external stakeholders (investors, regulators, enterprise clients).
  
  
• Bachelor’s degree preferred.

Skills & Traits

• Japanese language (spoken and written) proficiency preferred
• Exceptional written and verbal communication.
  
  
• Strategic thinker with strong prioritization and judgment.
  
  
• High emotional intelligence; skilled at navigating sensitive, high-stakes contexts.
  
  
• Operates independently and anticipates needs before they arise.
  
  
• Meticulous, detail-oriented, and highly organized.
  
  
• Comfortable managing confidential information and complex decision environments.
  
  
• Able to context-switch, manage ambiguity, and maintain composure under pressure.
  
  
• Proactively supports executive goals, objectives, and KPIs.

Technical Proficiency

• Strong proficiency in Google Suite, Slack, Confluence, JIRA, and Microsoft Office (Word, Excel, PowerPoint, Outlook).
• Strong presentation-building capability.
• Quick to learn and adopt new systems