Sterling Readiness
Group

Know your team is ready before it counts

We help defense, security, and operations teams test decisions, find readiness gaps, and practice responses with AI-enabled exercises.Prepare for global threats across the spectrum of Multi-Domain Operations: Air, Land, Sea, Cyber, and Space.

Fight. Flight. Freeze.Which is your team?

The risk

Untested readiness is an assumption.

A plan can look sound until conditions change. Untested decisions leave gaps hidden until the stakes are real.

Exercise the plan. Find the gap. Give your team another rep. Prepare for anything.

Products

Four ways to put readiness to the test.

eWar.AI

Built for

Commanders, training officers, planners, and program managers

The readiness gap

Manual scenario design takes weeks and relies on fixed scripts. Generate adaptive war games in hours with recorded decision reviews. Integrate artificial intelligence (AI) and increase reps.

Explore eWar.AI

Cyber Ambush

Built for

Security teams, SOC leads, training managers, and IT leadership

The readiness gap

Generic tabletop exercises often miss how adversaries actually maneuver. Practice detection, triage, and containment against real-world attacker tradecraft. Leverage AI to develop and refine in real-time.

Explore Cyber Ambush

Sky Ambush

Built for

Base security, event safety, and critical-infrastructure teams

The readiness gap

Commercial drone incursions force split-second decisions under pressure. Rehearse recognition, reporting, and countermeasures within legal limits. Detailed guidance from OSINT.

Explore Sky Ambush

MDMP.si

Built for

Battle staffs, commanders, planners, and military students

The readiness gap

Military Decision-Making Process (MDMP) training stalls on static slides and printed aids. Accelerate all seven steps with collaborative sessions and a super intelligence (SI) coach.

Explore MDMP.si
See the full portfolio

Why Sterling

Experience that shapes the exercise.

Operator-led experience

Military intelligence, contingency planning, and wargaming experience inform how we design exercises.

Security meets legal judgment

Information-security expertise and legal experience connect technical exposure to decisions leaders can act on.

Realistic opposition

Exercises use adversary behavior and adaptive decisions, not just a fixed script.

Repeatable practice

AI-generated scenarios help teams get more repetitions without the cost of another live exercise.

Measurable decisions

Recorded objectives, decisions, and timing support honest after-action review.

The requirement comes first

We simplify the problem and optimize the process before applying AI or automation.

Our method

From requirement to a tested response.

  1. 01

    Define the threat

    Identify what your team needs to be ready for, along with the constraints.

  2. 02

    Model the risk

    Build a realistic scenario around the decisions and consequences that matter.

  3. 03

    Build the capability

    Practice the essential skills and refine the process before automating it.

  4. 04

    Prove it under pressure

    Exercise the plan, measure the result, and report the gap honestly.

Who we serve

Different teams. Real consequences.

Defense and government

Training officers, planners, and program managers preparing teams across land, sea, air, space, and cyber.

Security and IT teams

Security teams, SOC leads, and IT leadership practicing detection, response, and escalation.

Facilities and events

Base security, event safety, and critical-infrastructure teams responsible for their areas of operation.

Proof of readiness

Dig into what the exercise leaves behind.

Readiness needs evidence: recorded decisions, identified gaps, and responses your team has practiced.

Decisions you can review

eWar.AI records objectives, player decisions, and timing for after-action review.

See eWar.AI

Gaps you can act on

Cyber Ambush tracks defensive skills and turns exercise debriefs into a concrete hardening list.

See Cyber Ambush

Responses you can rehearse

Sky Ambush provides recognition training and decision drills aligned with the authorities operators actually have.

See Sky Ambush

Plans you can stress-test

MDMP.si guides staffs through all seven planning steps and wargames courses of action against an AI opposing force.

See MDMP.si

The founders

The officer and the counsel.

Joshua Witt

Co-founder

Joshua Witt

U.S. Army Reserve Military Intelligence Officer · MBA · CSP

More than 20 years across technology, industry, and military affairs, with experience in wargaming, contingency operations, and program management.

Michael Witt

Co-founder

Michael Witt

Attorney · CISSP · CCSP · CISM · CISA · HCISPP · PCI QSA

Legal and information-security experience spanning privacy, cloud security, compliance, incident response, and executive risk reporting.

Meet the founders

Your next step

Fight. Flight. Freeze. Which is your team?

Tell us what your team needs to be ready for. We will reply to arrange a time.

Bring your requirement, timeline, and biggest constraint.

support@sterlingllc.com