Application Guide

How to Apply for Deputy Director of Investigations

at The Sentry

🏢 About The Sentry

The Sentry is unique as an investigative organization that specifically targets the financial networks enabling conflict and corruption, using forensic financial investigations to expose illicit flows from war zones to global financial centers. Working here offers the opportunity to directly combat kleptocracy and predatory networks through evidence-based investigations that drive policy change and accountability.

About This Role

As Deputy Director of Investigations, you'll oversee the entire investigative lifecycle from pitch to publication, serving as developmental editor while managing security risks across physical, legal, cyber, and reputational domains. This role directly impacts The Sentry's mission by ensuring investigations meet evidentiary standards and strategically target illicit financial flows supporting conflict and corruption.

💡 A Day in the Life

A typical day involves reviewing investigative pitches and outlines, providing developmental feedback on draft reports, conducting security assessments for ongoing investigations, and coordinating with investigators to identify financial patterns in conflict-affected regions. You might spend the morning editing a report on illicit gold flows and the afternoon developing risk mitigation plans for fieldwork in a high-risk jurisdiction.

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Interview Prep

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🎯 Who The Sentry Is Looking For

  • Has 7+ years of investigative supervision experience with published work demonstrating superior developmental editing skills
  • Possesses expertise in conducting security risk assessments for sensitive investigations involving conflict zones or kleptocratic networks
  • Can balance multiple complex investigations while meeting deadlines in fast-paced environments
  • Has specific experience tracking illicit financial flows related to conflict, corruption, or natural resource exploitation

📝 Tips for Applying to The Sentry

1

Highlight specific investigations you've supervised that involved tracking money across borders or exposing financial networks

2

Include examples of how you've managed security risks (physical, legal, cyber) for sensitive investigations

3

Demonstrate your developmental editing skills by describing how you've shaped investigative narratives from raw findings to publication

4

Show familiarity with The Sentry's existing investigations by referencing specific reports or methodologies in your application

5

Quantify your supervisory experience (number of investigators managed, publications overseen, investigations completed)

✉️ What to Emphasize in Your Cover Letter

['Your experience supervising investigations that follow money trails across jurisdictions', 'Specific examples of developmental editing that improved investigative outcomes or impact', "How you've balanced multiple complex projects while maintaining security protocols", "Why The Sentry's focus on financial investigations targeting conflict networks aligns with your expertise"]

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🔍 Research Before Applying

To stand out, make sure you've researched:

  • → Review The Sentry's published investigations (especially those on Sudan, CAR, DRC) to understand their methodology and focus areas
  • → Study their policy recommendations and how investigations translate to advocacy impact
  • → Research their partnerships with media outlets and how they ensure investigative reach
  • → Understand their security protocols by reviewing any public statements about investigator safety
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💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Describe your process for conducting security risk assessments for investigations in conflict-affected regions
2 How would you develop an investigative pitch targeting illicit financial flows in a specific conflict zone?
3 Walk us through your developmental editing approach for turning raw investigative findings into compelling narratives
4 How do you prioritize and balance multiple investigations with different evidentiary requirements and deadlines?
5 What methodologies would you use to track natural resource exploitation through financial networks?
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⚠️ Common Mistakes to Avoid

  • Applying with only generic investigative experience without specific examples of financial investigations or conflict zone work
  • Failing to demonstrate understanding of The Sentry's unique model combining investigations with policy advocacy
  • Not addressing security considerations for sensitive investigations in your application materials

📅 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 The Sentry!

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