Deputy Director of Investigations

POSITION DESCRIPTION

Location: Remote

Full-Time

Salary Range: $115,000-$135,000

Reports To: Director Of Progams

About The Sentry

The Sentry is an investigative and policy organization that seeks to disable multinational predatory networks that benefit from violent conflict, repression, and kleptocracy.

Pull back the curtain on wars, mass atrocities, and other human rights abuses, and you’ll find grand corruption and unchecked greed. These tragedies persist because the perpetrators rarely face meaningful consequences. The Sentry aims to alter the warped incentive structures that continually undermine peace and good governance. Our investigations follow the money as it is laundered from war zones to financial centers around the world. We provide evidence and strategies for governments, banks, and law enforcement to hold the perpetrators and enablers of violence and corruption to account. These efforts provide new leverage for human rights, peace, and anti-corruption efforts.

Position Overview

The Sentry is seeking an experienced investigator to serve as Deputy Director of Investigations (DDI). The DDI will be responsible for directing and supervising investigations as well as executing developmental edits and quality assurance processes for all investigative reports. The DDI works with investigators and collaborates with other team members to produce high-quality and high-impact reports and materials to engage a range of audiences, from experts and policymakers to law enforcement, journalists, influencers, and the general public. The DDI also assists in identifying, executing, and providing timely deliverables to donors.

Key Responsibilities

Investigations

• Work with investigators and others to identify and conceptualize impactful investigations in The Sentry’s program areas with a focus on identifying illicit financial flows that support conflict, corruption, and natural resource exploitation.
• Supervise investigations from inception to publication, including pitches, outlines, risk assessment reports, drafts, and developmental edits, while meeting agreed upon timelines and keeping others in the organization apprised of key developments.
• Ensure investigations are consistent with The Sentry’s mission, strategic priorities, evidentiary requirements, and donor commitments.
• Oversee issuances of requests for comment in consultation with the General Counsel, working with investigators, communications team members, and others as needed.
• Work with investigators to identify and contract with suitable consultants, performing necessary vetting, assisting with payments, and ensuring confidentiality when needed.
• Approve all plans for engagement of sources, consultants, and others to further investigations.
• Approve all plans for field investigations, ensuring they support investigation goals, meet ethical standards, and address all necessary safety protocols.
• Work with Development to ensure funding of investigations and other work, including but not limited to identifying potential donors, participating in pitching, and updating donors on progress.
• Engage in public and private briefings as needed to present investigative findings, leading those presentations where investigators are not available to participate.
• Provide expert advice to investigators and others on the collection of various kinds of evidence to support reports, including video, audio, and other digital evidence.
• Support The Sentry’s goal of being a leader in OSINT investigations, including using OSINT to follow the money.

Developmental Editing:

• Serve as developmental editor on all investigative projects published by The Sentry.
• Work with the Senior Editor as needed on investigative report outlines as well as developmental, line, and copy edits.
• Ensure alignment of written products with agreed investigative requirements, policy frameworks, strategic objectives, and The Sentry’s core mission.
• Steward, implement, and maintain The Sentry’s voice across investigative products written by diverse authors as needed for a developmental edit and determined in consultation with the Senior Editor. [Same point as immediately above]
• Strengthen structure, sequencing, coherence, and clarity of content, ensuring that main ideas and policy points are presented powerfully and concisely.
• Evaluate, challenge, and bolster, as appropriate, the logic, coherence, and consistency of facts and arguments presented by authors.

Coaching and Mentoring:

• Work with investigators of varying skill and experience, providing constructive feedback and one-on-one coaching to improve investigative, reporting, and writing skills as needed.
• Review and give constructive feedback at every stage of investigation, from conception to final draft.
• Identify and provide training opportunities for investigators and The Sentry related to developing investigative, reporting, and writing skills.

Security

• Lead the assessment of physical security risks and ensure development of adequate plans to address identified risks. For legal, cyber, and reputational risks, work with the appropriate staff members, such as the General Counsel, to assess and address appropriately.
• Work with investigators to identify and assess risks throughout the lifetime of a product, reassessing as needed for changed circumstances.
• Work with others at The Sentry to identify technology to support security.

Other:

• Facilitate strong communication between investigators and others at The Sentry to ensure internal collaboration related to investigations and related policy work.
• Engage in administrative and organizational tasks as necessary.
• Other duties as assigned.

Required Experience and Qualifications:

• Bachelor’s degree.
• At least 7+ years of experience supervising investigations.
• A track record of authoring and supervising publications.
• Superior writing and developmental editing skills with at least five years of supervisory editorial experience.
• Organized and effective working in a fast-paced, rapid-response environment, balancing multiple projects and tasks while meeting deadlines.
• Well-developed decision-making, planning, organizational, problem-solving, and interpersonal skills.
• A high level of energy, dependability, creativity, initiative, and passion.
• Commitment to The Sentry’s mission and goals.

Preferred Experience and Qualifications:

• Advanced degree in relevant field.
• Foreign language skills, especially French or Arabic.
• Experience collecting evidence of various kinds, including in video and audio forms.
• Experience working on corruption, illicit finance, environmental crimes, human rights, or conflict investigations.
• Extensive experience with OSINT investigations, datasets, and tools.

Salary & Benefits:

The Sentry is committed to attracting, developing, and retaining exceptional people, and will pay a competitive salary for this position matching this commitment. Benefits include paid vacation leave, paid family and medical leave, health insurance including vision and dental plans, and 401k plan with employer match.

The Sentry is an Equal Opportunity Employer. We are committed to building a diverse and inclusive team and strongly encourage candidates from all backgrounds to apply. In compliance with federal, state and local laws, The Sentry’s work environment is safe and open to all employees and partners, respecting the full spectrum of race, color, religious creed, sex, gender identity, sexual orientation, national origin, ancestry, age, disability, marital status, familial status, genetic information, military or veteran status, domestic violence victim status, arrest or conviction record, or any other characteristic protected under applicable law. We are committed to providing reasonable accommodations for qualified individuals with disabilities and to ensuring equal opportunity in all aspects of employment, including recruitment, hiring, promotion, compensation, and contracting.

To apply, submit a resume and cover letter to jobs@thesentry.org by January 6, 2026. Please include “Deputy Director of Investigations" in the subject line of your email.