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Sitreps LLC

Head of Intelligence

Posted 8 Days Ago
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In-Office
New York, NY, USA
160K-190K Annually
Senior level
In-Office
New York, NY, USA
160K-190K Annually
Senior level
Lead and build the companys investigative intelligence function: conduct high-stakes OSINT investigations, map fraud networks, partner with engineering and data science to productize tradecraft, hire and manage an analyst team and budget, establish SOPs and quality standards, and represent investigative capability to enterprise customers and investors.
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Head of Intelligence

Location: New York City (On-Site)
Compensation: $160K–$190K base + meaningful early-stage equity + full benefits
Flexible for an exceptional candidate.
Reports to: CEO, CTO & COO

About the Client

We are a venture-backed intelligence platform helping insurers identify and prevent property and casualty fraud at scale. Our software combines open-source intelligence, network analysis, and machine learning to surface two things our customers cannot easily find on their own: individual claimants whose hidden online activity contradicts their reported claims, and the connected fraud rings behind organized claims schemes. Those rings look structurally similar to criminal or terrorist networks: interconnected nodes, leadership, accomplices, repeat patterns.

We have product-market fit. We have happy enterprise customers. We are heading into a Series A. The work is real and the upside is in front of us.

About the Role

We are hiring our first Head of Intelligence to build, own, and represent the investigative function that sits at the core of our product. You will start as an army of one. You will personally do the investigative work today: locating individuals behind aliases, surfacing hidden social media activity, mapping the conspirator networks behind organized claims schemes, and producing the intelligence outputs our enterprise customers rely on. You will partner with our engineering and data science teams to turn that work into systems that scale. Over the next twelve to eighteen months, the role grows. You will hire and lead a team of analysts. You will own the budget. You will become the named face of our intelligence capability to enterprise insurance clients. When the head of special investigations at a multi-billion-dollar carrier wants to understand how we illuminate the fraud rings in their book, you are the person they meet. When investors want to know who is behind the intelligence platform, you are the answer.This is a builder seat. There is no existing playbook for what you will be building. The right person is energized by that.

Responsibilities
  • Personally conducting the highest-stakes investigations: identifying individuals, aliases, and hidden post-claim activity; mapping the fraud networks behind organized claims rings
  • Hiring and building the intelligence team and managing the budget that supports it
  • Partnering with our engineering and data science teams to translate investigative tradecraft into structured data signals, workflows, and product features
  • Identifying and onboarding off-the-shelf intelligence, analytic, and OSINT tools where they accelerate the work
  • Establishing the SOPs, quality standards, and documentation practices that let the function scale without losing rigor
  • Producing intelligence outputs that support enterprise customer investigations, litigation, and decision-making
  • Representing our intelligence capability to enterprise insurance customers post-contract: explaining methodology, demonstrating value, and serving as the technical credibility behind the relationship
  • Showing up in Series A investor conversations as the intelligence leader behind the platform
Requirements Must-Haves
  • Deep intelligence background. Military, federal, or distinguished private-sector intelligence experience. You have personally targeted human beings and the networks around them. You think in relationships and structures, not just individual records.
  • A signal of supreme success on your resume. Top-tier academic background, distinguished military service in selective units or roles, or demonstrated excellence at a high-bar employer. When you describe what you have done, the room leans in.
  • Bias for action. You build before there is a playbook. Give you intent and a deadline and you go. You have a track record of standing up something new, not just executing something that already existed.
  • Hands-on today, leader tomorrow. You are not done doing the work. Years of experience matter less than whether you are still the person rolling up your sleeves.
  • Customer fluency. You can stand in front of an enterprise client and explain in detail how an investigation was run, why it matters, and what we caught. You are a product evangelist by temperament, not just an operator.
  • Technically conversational. You do not need to write code. You do need to sit with an engineer and articulate what an investigative workflow actually requires.
  • Five days a week on-site in NYC. Being in the room with the executive team and engineering is part of how this role works.
Nice-to-Haves
  • Military intelligence officer or NCO background, especially in roles focused on targeting individuals or human networks (SOF intel, MARSOC, Ranger intel, JSOC, MI officer at a selective unit, federal HUMINT-equivalent)
  • Federal intelligence or law enforcement experience at the working officer level (FBI, CIA, DIA, NSA, NCTC, financial-crimes squads)
  • Current or recent experience at a high-pedigree defense, intelligence, or technology employer where you are no longer building the kind of new thing you want to build next
  • Experience presenting intelligence or investigative work to senior external audiences: federal partners, enterprise customers, executive leadership, or investors
  • Familiarity with commercial OSINT, intelligence, or analytic platforms (Palantir, Maltego, Babel Street, Recorded Future, Skopenow, ShadowDragon, etc.). Welcome but trainable; we will not gate on tools.
  • Spanish, Portuguese, or other relevant language capability
Compensation & Benefits
  • $160K to $190K base plus equity, 100% employer-paid medical, dental, and vision
Why This Role
  • Direct ownership of a core function at a venture-backed company with product-market fit and a clear path to Series A
  • A real seat at the table with the CEO, CTO, and COO from day one
  • A chance to define how investigative work scales through technology in a category that is wide open
  • The kind of role that compounds: build the function today, lead the team tomorrow, become the named intelligence pedigree behind a category-defining platform
  • Meaningful early-stage equity in a company where the upside is in front of it
What This Role Is Not
  • Not a pure execution-only OSINT seat. The work is real but the trajectory is leadership.
  • Not a place for someone who needs a playbook handed to them.
  • Not a strategy-from-a-distance or chief-of-staff-style seat.
  • Not a sales role, but customer-facing fluency is required.
  • Not for someone who has stopped touching investigative work.

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