Director of Investigations

Sitreps 2 Steercos
New York, NY

Head of Intelligence

Location: New York City (On-Site, 5 days) Compensation: $160K–$190K base + meaningful early-stage equity + full benefits. (Flexible for an exceptional candidate). Reports To: CEO, CTO & COO

About Us

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, and 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.


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 12 to 18 months, the role grows. You will hire and lead a team of analysts, own the budget, and become the named face of our intelligence capability to enterprise clients. When the head of special investigations at a multi-billion-dollar carrier wants to understand how we illuminate fraud rings, you are the person they meet. When investors want to know who is behind the platform, you are the answer.

This is a builder seat. There is no existing playbook. The right person is energized by that.


What You Will Own

  • High-Stakes Investigations: Personally identifying individuals, aliases, and hidden post-claim activity; mapping the fraud networks behind organized claims rings.
  • Team Building: Hiring and building the intelligence team and managing the budget that supports it.
  • Product Partnership: Working with engineering and data science teams to translate investigative tradecraft into structured data signals, workflows, and product features.
  • Tool Procurement: Identifying and onboarding off-the-shelf intelligence, analytic, and OSINT tools where they accelerate the work.
  • Operational Excellence: Establishing the SOPs, quality standards, and documentation practices that let the function scale without losing rigor.
  • Customer Facing & Evangelism: Representing our intelligence capability to enterprise customers post-contract—explaining methodology, demonstrating value, and serving as the technical credibility behind the relationship.
  • Investor Relations: Showing up in Series A investor conversations as the intelligence leader behind the platform.


What We Are Looking For

  • 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: Top-tier academic background, distinguished military service in selective units/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.
  • 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.
  • Technically Conversational: You do not need to write code, but you do need to sit with an engineer and articulate what an investigative workflow actually requires.
  • On-Site Presence: Five days a week on-site in NYC. Being in the room with the executive team and engineering is non-negotiable.


Strongly Preferred

  • Military intelligence officer or NCO background 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/recent experience at a high-pedigree defense, intelligence, or tech employer where you are no longer building the kind of new thing you want to build next.
  • Experience presenting intelligence to senior external audiences (federal partners, enterprise customers, executive leadership, investors).
  • Familiarity with commercial OSINT, intelligence, or analytic platforms (Palantir, Maltego, Babel Street, Recorded Future, Skopenow, ShadowDragon, etc.). Welcome but trainable.
  • Spanish, Portuguese, or other relevant language capability.


Why You Should Want This

  • 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.
  • $160K to $190K base + equity + benefits.


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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