Application Guide

How to Apply for Executive Assistant to the CEO & CTO (Founders)

at Irregular

🏢 About Irregular

Irregular appears to be an Israeli startup with global operations, given the need for managing US/Europe time zones and international travel. The company likely operates in a fast-paced, high-growth environment where supporting founders directly means you'll be at the center of strategic decisions and rapid scaling. Working here offers exposure to both CEO and CTO perspectives in what seems to be a tech-focused venture.

About This Role

This Executive Assistant role uniquely supports both the CEO and CTO (who are founders), requiring seamless coordination between leadership and product/technical functions. You'll be the operational backbone for founders managing complex calendars across time zones, international travel, and critical stakeholder communications. Your impact comes from protecting founders' focus time and ensuring smooth execution during pivotal moments like board meetings.

💡 A Day in the Life

Your day might start by coordinating a morning meeting with US stakeholders for the CEO while simultaneously preparing the CTO for a product review with European teams. You'd manage calendar conflicts, draft communications in both English and Hebrew, and potentially rearrange international travel plans that changed overnight. Throughout the day, you'd track action items from both business and technical meetings while ensuring founders have protected blocks for deep work.

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🎯 Who Irregular Is Looking For

  • Has 3+ years supporting C-level executives in startups or high-growth tech companies, not just corporate environments
  • Demonstrates proven ability to manage complex, last-minute changes to international travel and multi-timezone calendars without stress
  • Is bilingual in English and Hebrew with experience communicating professionally across US/European business cultures
  • Shows exceptional judgment in prioritizing conflicting demands between CEO and CTO needs

📝 Tips for Applying to Irregular

1

Highlight specific examples of managing calendars for executives across US/Europe time zones - mention actual time differences you've navigated

2

Demonstrate your startup/high-growth experience by describing how you've adapted to rapid changes and ambiguous situations

3

Include Hebrew language proficiency prominently in your resume and application materials

4

Showcase experience with both CEO and technical/CTO support - emphasize understanding of product/tech workflows

5

Provide concrete examples of 'protecting focus time' for executives and how you've handled last-minute travel changes

✉️ What to Emphasize in Your Cover Letter

['Your experience supporting founders or executives in startup environments specifically', "How you've successfully managed competing priorities between multiple senior leaders", 'Examples of handling international coordination across time zones and cultures', 'Your approach to maintaining calm efficiency during last-minute changes and high-pressure situations']

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Research Israeli startup culture and the typical pace/expectations in high-growth tech companies
  • → Look into common travel routes and challenges between Israel, Europe, and the US for business travel
  • → Investigate the tech/startup ecosystem in Israel to understand the environment Irregular operates within
  • → Try to identify if Irregular has specific industry focus (tech, SaaS, etc.) through any available online presence

💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Describe a time you had to manage conflicting calendar requests between two executives - how did you prioritize?
2 Walk through how you would handle a last-minute international travel change requiring visa adjustments
3 How do you ensure action items from technical meetings (with CTO) versus business meetings (with CEO) are tracked differently?
4 What systems have you used to manage time zones for US/Europe meetings, and how do you prevent scheduling errors?
5 How would you handle a situation where both founders need your support simultaneously during a critical board meeting preparation?
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⚠️ Common Mistakes to Avoid

  • Applying with only corporate/established company EA experience without highlighting startup adaptability
  • Not clearly demonstrating Hebrew language proficiency or international work experience
  • Presenting as someone who needs clear structure and predictable schedules rather than thriving in ambiguity

📅 Application Timeline

This position is open until filled. However, we recommend applying as soon as possible as roles at mission-driven organizations tend to fill quickly.

Typical hiring timeline:

1

Application Review

1-2 weeks

2

Initial Screening

Phone call or written assessment

3

Interviews

1-2 rounds, usually virtual

✓

Offer

Congratulations!

Ready to Apply?

Good luck with your application to Irregular!

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